CN112437786A - Polyimide solution and polyimide - Google Patents
Polyimide solution and polyimide Download PDFInfo
- Publication number
- CN112437786A CN112437786A CN202080003434.0A CN202080003434A CN112437786A CN 112437786 A CN112437786 A CN 112437786A CN 202080003434 A CN202080003434 A CN 202080003434A CN 112437786 A CN112437786 A CN 112437786A
- Authority
- CN
- China
- Prior art keywords
- polyimide
- mass
- solution
- present
- solvent
- 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 title claims abstract description 243
- 229920001721 polyimide Polymers 0.000 title claims abstract description 243
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000002723 alicyclic group Chemical group 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- 230000009477 glass transition Effects 0.000 claims description 6
- 239000010408 film Substances 0.000 description 59
- 239000002904 solvent Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 38
- 238000000576 coating method Methods 0.000 description 25
- 239000011248 coating agent Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 22
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 239000011521 glass Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 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 description 14
- 238000003756 stirring Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 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 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- OVASAEXSPYGGES-UHFFFAOYSA-N C1C2C(C(OC3=O)=O)C3C1CC2(C1=O)CCC21CC1CC2C2C(=O)OC(=O)C12 Chemical compound C1C2C(C(OC3=O)=O)C3C1CC2(C1=O)CCC21CC1CC2C2C(=O)OC(=O)C12 OVASAEXSPYGGES-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 229920005575 poly(amic acid) Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FMACFWAQBPYRFO-UHFFFAOYSA-N 5-[9-(1,3-dioxo-2-benzofuran-5-yl)fluoren-9-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 FMACFWAQBPYRFO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic diamines Chemical class 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000002070 nanowire Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- LCCYEGJIEFWDSA-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)=C1 LCCYEGJIEFWDSA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 2
- HOOIIRHGHALACD-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(O)=O)C(C)=CC1C1C(=O)OC(=O)C1 HOOIIRHGHALACD-UHFFFAOYSA-N 0.000 description 2
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RPYFJVIASOJLJS-UHFFFAOYSA-N [3-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1CC2C(CN)C(CN)C1C2 RPYFJVIASOJLJS-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- MQQRFOXFIPBFOV-UHFFFAOYSA-N 1,2-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C(O)=O)C1(C)C(O)=O MQQRFOXFIPBFOV-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- SBHHKGFHJWTZJN-UHFFFAOYSA-N 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C)(C(O)=O)C1C(O)=O SBHHKGFHJWTZJN-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- QTMABCAIKABEFK-UHFFFAOYSA-N 2-[4-[9-[4-(2-aminophenoxy)phenyl]fluoren-9-yl]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC=3C(=CC=CC=3)N)=CC=2)C=C1 QTMABCAIKABEFK-UHFFFAOYSA-N 0.000 description 1
- UNVRXFDNODGYNP-UHFFFAOYSA-N 2-amino-4-(9h-fluoren-1-yl)phenol Chemical compound C1=C(O)C(N)=CC(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)=C1 UNVRXFDNODGYNP-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- SFHLLWPKGUSQIK-UHFFFAOYSA-N 2-methylcyclohexane-1,4-diamine Chemical compound CC1CC(N)CCC1N SFHLLWPKGUSQIK-UHFFFAOYSA-N 0.000 description 1
- RIQIAIDMIAVZAZ-UHFFFAOYSA-N 2-methylpentane-1,1-diamine Chemical compound CCCC(C)C(N)N RIQIAIDMIAVZAZ-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- JASHGAIOBWYPBI-UHFFFAOYSA-N 3a,4a,7a,7b-tetrahydrodifuro[5,4-a:5',4'-d]furan-1,3,5,7-tetrone Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C1O2 JASHGAIOBWYPBI-UHFFFAOYSA-N 0.000 description 1
- HVSOOROWXIVZSH-UHFFFAOYSA-N 4-(9H-fluoren-1-yl)-2-fluoroaniline Chemical compound NC1=C(C=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2)F HVSOOROWXIVZSH-UHFFFAOYSA-N 0.000 description 1
- RGVHBPPWCQVMDR-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21 RGVHBPPWCQVMDR-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- RDPQVEHCWKPHFR-UHFFFAOYSA-N 4-[2-(9H-fluoren-1-yl)phenoxy]aniline Chemical compound NC1=CC=C(OC2=C(C=CC=C2)C2=CC=CC=3C4=CC=CC=C4CC23)C=C1 RDPQVEHCWKPHFR-UHFFFAOYSA-N 0.000 description 1
- FNJFWOJEIGPYAS-UHFFFAOYSA-N 4-[4-(9h-fluoren-1-yl)phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)C=C1 FNJFWOJEIGPYAS-UHFFFAOYSA-N 0.000 description 1
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- KZJIOVQKSAOPOP-UHFFFAOYSA-N 5,5-dimethylhex-1-ene Chemical class CC(C)(C)CCC=C KZJIOVQKSAOPOP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FPGSTPKCNFSZQZ-UHFFFAOYSA-N 5-(3,4-dioxooxolan-2-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1OCC(=O)C1=O FPGSTPKCNFSZQZ-UHFFFAOYSA-N 0.000 description 1
- LQOPXMZSGSTGMF-UHFFFAOYSA-N 6004-79-1 Chemical compound C1CC2C3C(=O)OC(=O)C3C1C2 LQOPXMZSGSTGMF-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VAALVBPLSFRYMJ-XXMNONFOSA-N O=C1OC(=O)[C@@H]([C@@H](C23)C4)[C@H]1[C@@H]4C3[C@@H]1C[C@H]2[C@H]2C(=O)OC(=O)[C@@H]12 Chemical compound O=C1OC(=O)[C@@H]([C@@H](C23)C4)[C@H]1[C@@H]4C3[C@@H]1C[C@H]2[C@H]2C(=O)OC(=O)[C@@H]12 VAALVBPLSFRYMJ-XXMNONFOSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- FOLJMFFBEKONJP-UHFFFAOYSA-N adamantane-1,3-diamine Chemical compound C1C(C2)CC3CC1(N)CC2(N)C3 FOLJMFFBEKONJP-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- XQBSPQLKNWMPMG-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O XQBSPQLKNWMPMG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- OWEZJUPKTBEISC-UHFFFAOYSA-N decane-1,1-diamine Chemical compound CCCCCCCCCC(N)N OWEZJUPKTBEISC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- IZKZIDXHCDIZKY-UHFFFAOYSA-N heptane-1,1-diamine Chemical compound CCCCCCC(N)N IZKZIDXHCDIZKY-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical compound CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007767 slide coating Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- KQAYXXFFBQKDEP-UHFFFAOYSA-N undecane-6,6-diamine Chemical compound CCCCCC(N)(N)CCCCC KQAYXXFFBQKDEP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
-
- 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
- C08G73/1075—Partially aromatic polyimides
-
- 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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/128—Unsaturated polyimide precursors the unsaturated precursors containing heterocyclic moieties in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
- H01B5/14—Non-insulated conductors or conductive bodies characterised by their form comprising conductive layers or films on insulating-supports
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
The invention provides a polyimide having a small yellowness index and excellent heat resistance, and a polyimide solution containing the polyimide. The polyimide is a mixture of a polyimide (I) comprising a repeating unit represented by the specific formula (1) and a polyimide (II) comprising a repeating unit represented by the specific formula (2), wherein the content of the polyimide (I) is 5 to 95% by mass and the content of the polyimide (II) is 95 to 5% by mass.
Description
Technical Field
The present invention relates to a polyimide solution and polyimide.
Background
Currently, glass substrates are used for various display devices such as liquid crystal displays and organic Electroluminescence (EL) displays. Glass substrates are excellent in terms of high heat resistance, low linear thermal expansion coefficient, and high transparency, while weight reduction and flexibility of materials and resistance to impacts that can be received in daily life are required, and materials replacing glass are being sought, and therefore, studies on polyimide materials have been made.
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 6010533
Disclosure of Invention
Problems to be solved by the invention
In general, many polyimides are insoluble in a solvent, and a method of converting into a polyimide via a polyamic acid which is a polyimide precursor soluble in a solvent is widely employed in order to industrially stably obtain a cured material. Since this conversion requires heating at 300 ℃ or higher, the heat load is high, and this causes a failure of the apparatus even during dehydration. The obtained material is often not free from yellowing, and mounting of the material on an electronic device is limited to internal components of a housing such as an internal substrate. This yellowing property (more specifically, yellowness index) cannot be prevented even when a fluorene structure is introduced, and this may impair the expansion of applications.
The yellowing of polyimide materials is due to the continuous structure of a conjugated system, known as a Charge Transfer (CT) complex, where Charge Transfer can occur. Further, it is considered that charge transfer between molecules is also a cause of yellowing in a structure having high planarity with a 5-or 6-membered ring as a base axis, which is characteristic in the chemical structure of polyimide.
Therefore, in order to achieve transparency of polyimide, a method of adding a certain amount of an aliphatic structure to a constituent material to suppress coloring of the material is generally known. On the other hand, the tendency of the glass transition temperature (Tg) of the material to decrease is accompanied by a decrease in heat resistance.
In view of the above circumstances, an object of the present invention is to provide a polyimide having a small yellowness index and excellent heat resistance, and a polyimide solution containing the polyimide.
Means for solving the problems
The present inventors have conducted intensive studies on the above-mentioned problems, and as a result, have found that the above-mentioned problems can be solved by using two types of polyimides having specific structures in combination, and have completed the present invention.
That is, the present inventors have found that the above problems can be solved by the following means.
(1) A polyimide solution comprising: a polyimide (I) comprising a repeating unit represented by the following formula (1) and a polyimide (II) comprising a repeating unit represented by the following formula (2),
the content of the polyimide (I) is 5 to 95% by mass and the content of the polyimide (II) is 95 to 5% by mass based on the total amount of the polyimide (I) and the polyimide (II).
(2) A polyimide which is a mixture of a polyimide (I) comprising a repeating unit represented by the following formula (1) and a polyimide (II) comprising a repeating unit represented by the following formula (2),
the content of the polyimide (I) is 5 to 95% by mass, and the content of the polyimide (II) is 95 to 5% by mass.
(3) The polyimide according to the above (2), which has a glass transition temperature of 280 ℃ or higher.
(4) The polyimide according to the above (2) or (3), which has a yellowness index of 3 or less.
(5) A conductive film comprising a polyimide layer formed from the polyimide according to any one of the above (2) to (4).
ADVANTAGEOUS EFFECTS OF INVENTION
As shown below, according to the present invention, a polyimide having a small Yellowness Index (YI) and excellent heat resistance, and a polyimide solution containing the polyimide can be provided.
Detailed Description
The polyimide of the present invention, the polyimide solution of the present invention, and the like will be described below.
In the present specification, the numerical range expressed by the term "to" includes the numerical values described before and after the term "to" as the lower limit value and the upper limit value.
Further, each component may be used alone in 1 kind, or two or more kinds may be used in combination. Here, when two or more kinds of the components are used in combination, the content of the components means the total content unless otherwise specified.
In the present invention, it is preferable to treat a solution suitable for intramolecular reaction under mild conditions until imide ring-closure reaction occurs, while limiting the composition so as to satisfy both the presence of a repeating unit that does not generate a conjugated system that forms a CT complex and the solubility in a solvent. The solutions containing the obtained compositions are stored separately and mixed before use, so that formation of a continuous structure of aromatic components can be avoided even in long-term aging storage, and a technique for stably obtaining a material with high transparency can be provided.
[ polyimide ]
The polyimide of the present invention comprises a polyimide (I) composed of a repeating unit represented by formula (1) described below and a polyimide (II) composed of a repeating unit represented by formula (2) described below, wherein the content of the polyimide (I) is 5 to 95% by mass and the content of the polyimide (II) is 95 to 5% by mass.
Since the polyimide of the present invention has such a structure, the above-described effects are considered to be obtained. The reason for this is not clear, but is assumed to be as follows.
As described above, the polyimide of the present invention is a mixture of the polyimide (I) and the polyimide (II). Here, as described later, since the polyimide (I) and the polyimide (II) are each formed of a repeating unit having a structure in which an aromatic group and an aliphatic group are bonded to each other, a conjugated system is not generated. In addition, the present invention is greatly characterized in that two types of polyimides having a structure with contrast are used in combination. That is, in the polyimide (I), an aromatic group having a fluorene skeleton is sandwiched by carbonyl groups, and an aliphatic group or an alicyclic group is sandwiched by nitrogen atoms. In contrast, in the polyimide (II), an aliphatic group or an alicyclic group is sandwiched by carbonyl groups, and an aromatic group having a fluorene skeleton is sandwiched by nitrogen atoms. In the mixture of the two types of polyimides, the imide groups of the two types of polyimides interact with each other to form a structure in which the aromatic group of the polyimide (I) and the aliphatic group or alicyclic group of the polyimide (II) are stacked, or the aliphatic group or alicyclic group of the polyimide (I) and the aromatic group of the polyimide (II) are stacked. Therefore, it is considered that the polyimide of the present invention has extremely small charge transfer not only in the molecule but also between the molecules, and as a result, coloring is suppressed.
The following describes the polyimide (I) and the polyimide (II) contained in the polyimide of the present invention.
Polyimide (I)
The polyimide (I) is a polyimide composed of a repeating unit represented by the following formula (1).
[ chemical formula 1]
In the formula (1), A1Represents a 4-valent aromatic group having a fluorene skeleton. B is1Represents a 2-valent aliphatic group or alicyclic group.
As described above, in formula (1), A1Represents a 4-valent aromatic group having a fluorene skeleton. The above-mentioned 4-valent aromatic group having a fluorene skeleton may have a substituent.
As described above, B1Represents a 2-valent aliphatic group or alicyclic group. The above-mentioned "2-valent aliphatic group or alicyclic group" optionally has a substituent (but does not contain a fluorene skeleton).
The reason why the YI is smaller, the heat resistance is more excellent, and the absolute refractive index is smaller is that B1Preferably a 2-valent alicyclic group. Hereinafter, the smaller YI and the more excellent heat resistance are also referred to as "the more excellent effects and the like of the present invention".
Synthesis of polyimide (I)
The method for synthesizing the polyimide (I) is not particularly limited, and the polyimide of the present invention obtained is preferably polymerized by adding tetracarboxylic acid or an acid anhydride thereof (acid component) and diamine (amine component) to a solvent (method 1) from the viewpoint of smaller YI, more excellent heat resistance and smaller absolute refractive index. Thus, a solution containing the polyimide (I) can be obtained. Hereinafter, the polyimide of the present invention obtained with a smaller YI and a more excellent heat resistance is also referred to as "more excellent effects of the present invention and the like".
(acid component)
The acid component in the above method 1 is a compound having a fluorene skeleton (aromatic compound) and having 4 carboxyl groups or an acid anhydride thereof. Among these, acid anhydrides are preferable, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride (BPAF), 9-bis [4- (3, 4-dicarboxyphenoxy) phenyl ] fluorene dianhydride are more preferable, and BPAF is even more preferable, because the effects of the present invention and the like are even more excellent.
(amine component)
The amine component in the above method 1 is an aliphatic group or an alicyclic group, and it has 2 amino groups. Specific examples thereof include: straight-chain or branched-chain aliphatic diamines such as diaminobutane, diaminopentane, diaminohexane, diaminoheptane, diaminooctane, diaminononane, diaminodecane, diaminoundecane, diaminododecane, and 2-methyl-diaminopentane; 1, 4-diaminocyclohexane, 1, 3-diaminocyclohexane, 1, 2-diaminocyclohexane, 3-methyl-1, 4-diaminocyclohexane, 3-methyl-3-aminomethyl-5, 5-dimethyl-1-cyclohexylamine (isophoronediamine) (IPDA), 1, 3-bisaminomethylcyclohexane, bis (4,4 ' -aminocyclohexyl) methane, bis (3,3 ' -dimethyl-4, 4 ' -aminocyclohexyl) methane, bis (aminomethyl) norbornane, bis (aminomethyl) -tricyclo [5,2,1,0] decane, 1, 3-diaminoadamantane, 2 ' -dimethyl-4, 4 ' -methylenebis (cyclohexan-1-ylamine), Diamines having an alicyclic structure such as 4, 4' -methylenebis (cyclohexylamine); and the like. Among these, from the viewpoint of further improving the effects and the like of the present invention, a diamine having an alicyclic structure is preferable, and IPDA is more preferable. The compound may have an aromatic ring in a part thereof as long as it does not affect formation of a CT complex at an imide site.
(solvent)
The solvent in the above method 1 is not particularly limited as long as it is a solvent capable of dissolving the polyimide (I), and an amide solvent such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone, etc.; cyclic ester solvents such as γ -butyrolactone, γ -valerolactone, δ -valerolactone, γ -caprolactone, e-caprolactone, α -methyl- γ -butyrolactone and the like; carbonate solvents such as ethylene carbonate and propylene carbonate; glycol solvents such as triethylene glycol; phenol solvents such as m-cresol, p-cresol, 3-chlorophenol, and 4-chlorophenol; acetophenone; 1, 3-dimethyl-2-imidazolidinone; sulfolane; dimethyl sulfoxide; and the like. In addition, other common organic solvents, that is, phenol, o-cresol, butyl acetate, ethyl acetate, isobutyl acetate, propylene glycol methyl ether acetate, ethyl cellosolve, butyl cellosolve, 2-methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, tetrahydrofuran, dimethoxyethane, diethoxyethane, dibutyl ether, diethylene glycol dimethyl ether, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, acetone, butanol, ethanol, and the like can also be used. These solvents may be used in combination of a plurality of them.
(molar ratio)
The molar ratio of the acid component to the amine component (acid component/amine component) in the above method 1 is not particularly limited, but is preferably 0.90 to 1.10, more preferably 0.95 to 1.05, from the viewpoint of further improving the effects of the present invention.
(suitable mode for method 1)
The polymerization temperature is not particularly limited, but is preferably 50 to 100 ℃ for the reason of further excellent effects of the present invention and the like.
The polymerized polyamic acid may be imidized (thermal imidized) by a thermal method in which the solution is directly heated, or may be chemically imidized using a reactant. The term "thermal imidization" as used herein refers to a method of imidizing by heating without using a dehydrating agent or an imidization accelerator. Specifically, for example, a method of heating a polyamic acid solution to obtain a polyimide solution is given. As the solvent used for preparing the polyamic acid solution, for example, the same solvent as used in the polymerization can be used. Specific examples and suitable modes of the solvent are the same as those of the solvent of the polyimide solution described later.
The heating time in the thermal imidization varies depending on the amount of treatment of the polyimide unit to be subjected to dehydration ring closure and the heating temperature, and is preferably in the range of 10 minutes to 5 hours after the treatment temperature reaches the maximum temperature.
Further, the treatment can be carried out for about 1 to 5 hours while actively removing product water generated by dehydration and ring closure from the system by adding a solvent azeotropic with water, such as toluene or xylene, to the solution containing the composition and raising the temperature to 170 to 200 ℃ by using an azeotropic method having a water azeotropic action. In order to carry out dehydration in a short time and at a low temperature, the pressure may be reduced.
Polyimide (II)
The polyimide (II) is a polyimide composed of a repeating unit represented by the following formula (2).
[ chemical formula 2]
In the formula (2), A2Represents a 4-valent aliphatic group or alicyclic group. B is2Represents a 2-valent aromatic group having a fluorene skeleton.
The reason why the effects and the like of the present invention are more excellent is that2Preferably a 4-valent alicyclic group.
As described above, in formula (2), A2Represents a 4-valent aliphatic group or alicyclic group. The above-mentioned "4-valent aliphatic group or alicyclic group" optionally has a substituent (but does not contain a fluorene skeleton).
As described above, in the formula (2), B2Represents a 2-valent aromatic group having a fluorene skeleton. The above-mentioned containing a fluorene skeletonThe aromatic group having a valence of 2 may have a substituent.
Synthesis of polyimide (II)
The method for synthesizing the polyimide (II) is not particularly limited, and a method (method 2) of adding tetracarboxylic acid or an acid anhydride thereof (acid component) and diamine (amine component) to a solvent and polymerizing them is preferable because the effect of the present invention is more excellent. Thus, a solution containing the polyimide (II) can be obtained.
(acid component)
The acid component in the above method 2 is an aliphatic group or an alicyclic group, and is a compound having 4 carboxyl groups or an acid anhydride thereof. Specific examples thereof include: (1S,2R,4S,5R) -Cyclohexanetetracarboxylic dianhydride, (cis, -1,2,4, 5-Cyclohexanetetracarboxylic dianhydride), (1S,2S,4R,5R) -Cyclohexanetetracarboxylic dianhydride, (1R,2S,4S,5R) -Cyclohexanetetracarboxylic dianhydride, bicyclo [2.2.2] octane-2, 3,5, 6-tetracarboxylic dianhydride, bicyclo [2.2.2] oct-7-ene-2, 3,5, 6-tetracarboxylic dianhydride, 5- (dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic anhydride (MCHDA), 4- (2, 5-dioxotetrahydrofuran-3-yl) -tetrahydronaphthalene-1, 2-dicarboxylic anhydride, Tetrahydrofuran-2, 3,4, 5-tetracarboxylic dianhydride, bicyclo-3, 3 ', 4,4 ' -tetracarboxylic dianhydride, butane-1, 2,3, 4-tetracarboxylic dianhydride (BuDA), 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 1, 3-dimethyl-1, 2,3, 4-cyclobutanetetracarboxylic dianhydride, 1, 4-dimethyl-1, 2,3, 4-cyclobutanetetracarboxylic dianhydride (CBDA), and norbornane-2-pentanone-2 ' -cyclo-5 ' -spiro-2 ' -norbornane-5, 5 ', 6,6 ' -tetracarboxylic dianhydride (CpODA), hexahydro-1H, 3H-4, 8-methanobenzo [1, 2-c: 4,5-c '] difuran-1, 3,5, 7-tetraone (BHDA), hexahydro-1H, 3H-4, 8-ethanobenzo [1, 2-c: 4, 5-c' ] difuran-1, 3,5, 7-tetraone (BODA), decahydro-1H, 3H-4, 10: 5, 9-methanonaphtho [2, 3-c: 6,7-c '] difuran-1, 3,6, 8-tetraone (DNDA), dodecahydro- [5, 5' -diisobenzofuran ] -1,1 ', 3, 3' -tetraone, 5- (1, 4-phenylene) bis (hexahydro-4, 7-methanoisobenzofuran-1, 3-dione), 5-bis (hexahydro-4, 7-methanoisobenzofuran-1, 3-dione), ENEHYDE series manufactured by JXTG ENERGY, and the like. These compounds may be used in combination of two or more.
The acid component in the above method 2 is preferably an alicyclic group and is a compound having 4 carboxyl groups or an acid anhydride thereof, and more preferably an alicyclic group and is an acid anhydride of a compound having 4 carboxyl groups, for the reason that the effects and the like of the present invention are more excellent.
(amine component)
The amine component in the above method 2 is a compound (aromatic compound) having a fluorene skeleton and having 2 amino groups. Among these, from the viewpoint of further improving the effects and the like of the present invention, 2, 7-diaminofluorene, 9-bis (4-aminophenyl) fluorene (BAFL), 9-bis (4-aminophenoxyphenyl) fluorene, 9-bis (3-methyl-4-aminophenyl) fluorene, 9-bis (3-amino-4-hydroxyphenyl) fluorene, 9-bis (3-fluoro-4-aminophenyl) fluorene, or 9, 9-bis [4- (aminophenoxy) phenyl ] fluorene is preferable, and BAFL is more preferable.
(solvent)
The solvent in the above method 2 is not particularly limited as long as it is a solvent capable of dissolving the polyimide (II), and specific examples and suitable embodiments can be selected in view of the same effects as those of the solvent in the above method 1.
(molar ratio)
The molar ratio of the acid component to the amine component (acid component/amine component) in the above method 2 is not particularly limited, but is preferably 0.90 to 1.10, more preferably 0.95 to 1.05, from the viewpoint of further improving the effects of the present invention.
(suitable mode for method 2)
A suitable manner of the method 2 is the same as that of the method 1 described above.
Content
In the polyimide of the present invention, the content of the polyimide (I) is 5 to 95% by mass. Among these, for the reason of further improving the effects and the like of the present invention, the amount is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, still more preferably 30 to 70% by mass, particularly preferably 35 to 65% by mass, and most preferably 40 to 60% by mass.
In the polyimide of the present invention, the content of the polyimide (II) is 95 to 5% by mass. Among these, for the reason of further improving the effects of the present invention, the amount is preferably 90 to 10% by mass, more preferably 80 to 20% by mass, still more preferably 70 to 30% by mass, particularly preferably 65 to 35% by mass, and most preferably 60 to 40% by mass.
Glass transition temperature
The glass transition temperature of the polyimide of the present invention is preferably 280 ℃ or higher for the reason that the effect of the present invention is more excellent.
Yellowness index
The polyimide of the present invention preferably has a Yellowness Index (YI) of 3 or less for the reason that the effects of the present invention and the like are more excellent.
Manufacturing method
The method for producing the polyimide of the present invention is not particularly limited, and the following method a or the following method B is preferable because the effect of the present invention is more excellent.
Method A
Method A is as follows: the polyimide solution of the present invention described later is dried by heating or the like to remove the solvent in the polyimide solution, thereby obtaining the polyimide of the present invention.
For example, the polyimide of the present invention is obtained by applying a polyimide solution of the present invention described later to a substrate and drying the solution by heating or the like to remove the solvent from the polyimide solution.
(substrate)
The substrate may be selected so long as it is not attacked by the solvent of the polyimide solution of the present invention. For example, one can cite: glass; films formed of various resins such as cellulose Triacetate (TAC), polyethylene terephthalate (PET), cellulose diacetate, cellulose acetate butyrate, polyether sulfone, acrylic resins, polyurethane resins, polyesters, polycarbonates, polysulfones, polyethers, trimethylpentenes, polyether ketones, and (meth) acrylonitriles; metals such as SUS and copper; and the like. The substrate can be used as it is for a transparent material if it has excellent transparency. The substrate, if colored, can be used without detracting from its appearance.
The polyimide of the present invention suppresses the Yellowness Index (YI), and therefore, the base material can be selected on the premise that: the material is used for optical members and components having a coating layer with a limited refractive index, and particularly for display surfaces of image display devices such as Liquid Crystal Displays (LCDs), Cathode Ray Tubes (CRTs), Plasma Display Panels (PDPs), electroluminescent displays (ELDs), and touch panels.
The cured film obtained by smooth coating while ensuring the film thickness accuracy may be peeled off and treated as a film.
(coating)
As a method of coating on a substrate, for example, there can be used: roll coating, gravure coating, slide coating, spray coating, dipping, screen printing, spray coating, and the like.
(drying)
In terms of temperature control, the solvent may be evaporated and removed, and if the time and pressure are appropriately set, a material can be obtained even under conditions of a boiling point or lower.
Examples of the drying method include vacuum drying and hot air drying. The solvent contained in the polyimide solution is preferably dried in vacuum in order to completely dry the solvent, and the drying temperature is preferably in the range of 80 to 200 ℃ from the viewpoint of preventing decomposition of the residual solvent and deterioration of the resin due to the residual solvent.
The drying time may be selected so as to completely dry the solvent contained in the polyimide composition, and is preferably 15 hours or less from the viewpoint of the production process, and is preferably 8 hours or more from the viewpoint of sufficiently drying the residual solvent.
In the case of heating, it is preferably 200 ℃ or lower, more preferably 100 ℃ or lower, for the reason of further improving the effect of the present invention. The lower limit is not particularly limited, but is preferably 20 ℃ or higher, and more preferably 30 ℃ or higher, for the reason of further improving the effects of the present invention.
Method B
The method B includes the following steps: a precipitation step of adding a poor solvent to a polyimide solution of the present invention described later to precipitate a polyimide (I) and a polyimide (II) in the polyimide solution; a solvent removal step of removing the solvent from the polyimide solution after the precipitation step to obtain the polyimide of the present invention.
Since the polyimide ring-closure reaction is completed in the polyimide solution of the present invention, the polyimide solution is mixed with a poor solvent such as alcohol to precipitate the polyimide, and the polyimide solution is washed with a solvent as necessary and then dried to obtain the polyimide.
That is, the reaction solution imidized as described above is dropped into a large amount of a poor solvent to precipitate a polyimide, and the reaction solvent, a chemical imidizing agent, a catalyst, and the like are removed by washing, followed by drying, whereby a polyimide powder can be obtained.
The poor solvent that can be used is preferably a solvent that does not dissolve polyimide, and is not particularly limited, and water, methanol, ethanol, n-propanol, isopropanol, and the like are preferably selected from the viewpoints of affinity with the reaction solvent, the chemical imidization reagent, and ease of removal by drying.
When the polyimide solution containing a polyimide, an imidization accelerator and a dehydrating agent is put into a poor solvent, the solid content concentration of the polyimide solution is not particularly limited as long as the viscosity is a viscosity capable of stirring, and the concentration is preferably thin from the viewpoint of reducing the particle size of the polyimide to be precipitated. However, when the concentration is excessively low, the amount of the solvent used for precipitating the polyimide composition becomes large, which is not preferable.
From these viewpoints, the polyimide solution is preferably introduced into a poor solvent after the solid content concentration of the polyimide solution is diluted to 15 mass% or less, more preferably to 10 mass% or less. The amount of the poor solvent to be used is preferably equal to or more than the same amount as the polyimide solution, and more preferably 2 to 3 times. The polyimide obtained here preferably contains a small amount of an imidization accelerator and a dehydrating agent, and is therefore washed several times with the above-mentioned poor solvent.
[ polyimide solution ]
The polyimide solution of the present invention contains a polyimide (I) composed of a repeating unit represented by the above formula (1) and a polyimide (II) composed of a repeating unit represented by the above formula (2), and the content of the polyimide (I) is 5 to 95% by mass and the content of the polyimide (II) is 95 to 5% by mass, based on the total amount of the polyimide (I) and the polyimide (II).
The polyimide (I) and the polyimide (II) are as described above. The solvent is not particularly limited as long as it can dissolve the polyimide (I) and the polyimide (II), and specific examples and suitable modes are the same as those in the above-described method 1.
Content
In the polyimide solution of the present invention, the content of the polyimide (I) is 5 to 95% by mass based on the total amount of the polyimide (I) and the polyimide (II). Among these, for the reason of further improving the effects and the like of the present invention, the amount is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, still more preferably 30 to 70% by mass, particularly preferably 35 to 65% by mass, and most preferably 40 to 60% by mass.
In the polyimide of the present invention, the content of the polyimide (II) is 95 to 5% by mass based on the total amount of the polyimide (I) and the polyimide (II). Among these, for the reason of further improving the effects of the present invention, the amount is preferably 90 to 10% by mass, more preferably 80 to 20% by mass, still more preferably 70 to 30% by mass, particularly preferably 65 to 35% by mass, and most preferably 60 to 40% by mass.
Concentration
In the polyimide solution of the present invention, the solid content concentration of the polyimide solution is not particularly limited as long as it is a viscosity capable of stirring, and is preferably 5 to 50% by mass. The viscosity of the solution can be appropriately set to a viscosity that does not cause troubles during application, and is preferably 0.3 to 200 pas. The viscosity is a viscosity at normal temperature, i.e., 20 to 40 ℃.
Manufacturing method
The method for producing the polyimide solution of the present invention is not particularly limited, and examples thereof include the following methods: the solution containing the polyimide (I) and the solution containing the polyimide (II) are produced by the above-described method 1 and the above-described method 2, and the solution containing the polyimide (I) and the solution containing the polyimide (II) are mixed.
[ polyimide composition ]
The polyimide composition of the present invention is a composition containing the above-described polyimide of the present invention.
The polyimide composition of the present invention may contain components other than the above-described polyimide of the present invention. Examples of such components include: a crosslinkable resin, a thermosetting resin, an inorganic fiber (for example, glass fiber, carbon fiber, etc.), an oxidation stabilizer, a capping agent, a filler, a silane coupling agent, a sensitizer, a photopolymerization initiator, a sensitizer, and the like.
[ polyimide layer ]
The polyimide layer of the present invention is formed of the above-described polyimide of the present invention or the above-described polyimide composition of the present invention.
[ conductive film ]
The conductive film of the present invention includes the polyimide layer of the present invention.
The conductive film is, for example, a conductive film in which a wire layer having high conductivity is formed on a polyimide layer, and the wire layer exhibits a transmittance of 80% or more with respect to visible light.
Here, the polyimide layer is formed on the substrate, for example. Examples of the substrate include glass, polymers, inorganic semiconductor materials, inorganic dielectric materials, laminates thereof, and composites thereof. The substrate constitutes, for example, a touch sensor, a touch panel, a Liquid Crystal Display (LCD), a flat panel display, an Organic Light Emitting Diode (OLED), a solar cell, or the like.
The wire layer is formed of, for example, wires disposed on the surface of the polyimide layer.
In addition, the wire layer may be a conductive layer in which wires are enclosed in resin. The conductive layer can be formed by, for example, mixing a wire material with a resin and applying the mixture.
Examples of the wire material constituting the wire material layer include: metals such as silver, gold, indium, tin, iron, cobalt, platinum, palladium, nickel, cobalt, titanium, copper, and alloys thereof; a carbon material; and the like, and may be appropriately selected in consideration of conductivity and durability.
The wire rods may be arranged in a straight line to exhibit the target conductivity, or may have a mesh structure such as a mesh or lattice structure as necessary.
In order to ensure good transparency, the wire is preferably a fine nanowire (nanowire). The average diameter of the wire rod is preferably 250nm or less, more preferably 150nm or less, and still more preferably 120nm or less. On the other hand, the lower limit is not particularly limited, and is, for example, 10nm or more.
In order to obtain good electrical conductivity, a long wire rod is preferable, and specifically, for example, 5 μm or more is preferable. The upper limit is not particularly limited, and is, for example, 100 μm or less.
When the wire rod is obtained by patterning or the like, the wire rod can be formed under these conditions.
The conductive layer can be formed by appropriately selecting a common coating method such as dip coating, spray coating, knife edge coating, bar coating, mayer bar coating, slit coating, gravure coating, spin coating, plating, evaporation, printing, and transfer. In order to fix the wire, thermal or chemical melting may also be used.
The conductive film of the present invention can impart, for example, electrical conductivity to an organic material or the like which does not have electrical conductivity originally, or antistatic properties in a case where static electricity is not desired or may be dangerous. The conductive film of the present invention may be an optical film for obtaining various functions such as polarization, antireflection, phase shift, increase in luminance, and improvement in visibility.
In the polyimide layer of the present invention, a rigid fluorene skeleton is introduced into the molecule to avoid excessive mixing. As a result, the wire material such as a nanowire has high affinity for the expansibility at the time of thermal response. By making the expansibility of the polyimide layer closer to the expansibility of the wire layer, the polyimide layer also exhibits good followability to the wire layer even when a load such as a temperature change is applied to the conductive film of the present invention. Therefore, the strain and deterioration of the conductive film of the present invention can be reduced, and the product life can be improved.
Examples
The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The following physical property values were measured by the following methods.
The Yellowness Index (YI) was measured using a color difference meter (SE 7700, manufactured by Nippon Denshoku industries Co., Ltd.).
The glass transition temperature (Tg) was measured using a thermal analyzer (TMA-60 manufactured by Shimadzu corporation).
The Coefficient of Thermal Expansion (CTE) was measured using TMA-60 manufactured by Shimadzu corporation, with a measurement temperature range of 50 to 200 ℃ and a temperature rise rate of 10 ℃/min.
The surface resistivity was measured at 23 ℃ under a relative humidity of 50% using a 4-terminal 4-probe measuring apparatus (Loresta GP manufactured by Mitsubishi Chemical Analytich).
Polyimide solutions and polyimides were produced as described below, and then evaluated.
Comparative example 1
19.68g (43 mmol) of 9, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride (BPAF), 7.34g (43 mmol) of isophorone diamine (IPDA), 0.23g of oxalic anhydride, 0.59g of triethylamine, 120g of N-methyl pyrrolidone (NMP) and 40g of toluene were put in a three-necked flask, stirred at 40 ℃, and then heated and stirred at 200r.p.m. (round per minute) at a silicone oil bath temperature of 180 ℃ for 1 hour. To remove 40ml of the water-toluene fraction, heating was performed in a silicon oil bath, and stirring was continued in this state. Then, the reaction was stopped after 3 hours and 30 minutes to obtain a solution (15 mass%) containing polyimide 1. The polyimide 1 corresponds to the polyimide (I) described above.
The resulting solution was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Next, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes, and film formation of the coating film was attempted, but film formation was not performed.
Comparative example 2
Butane-1, 2,3, 4-tetracarboxylic dianhydride (BuDA)5.15g (26 mmol), 5- (2, 5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic dianhydride (MCHDA)2.37g (9 mmol), norbornane-2-spiro-2 ' -cyclopentanone-5 ' -spiro-2 ' -norbornane-5, 5 ', 6,6 ' -tetracarboxylic dianhydride (CpODA)3.07g (8 mmol), 9-bis (4-aminophenyl) fluorene (BAFL)15.02g (43 mmol), oxalic anhydride 0.23g, triethylamine 0.59g, N-methylpyrrolidone (NMP)120g, toluene 40g were put in a three-neck flask, stirred at 40 ℃ and then the temperature of the silicone oil bath was raised to 180 ℃, heating and stirring were carried out at a rotation speed of 200r.p.m. for 1 hour. Heating was carried out in a silicon oil bath for removing 40ml of the water-toluene fraction, and stirring was continued in this state. The reaction was stopped after 3 hours and 30 minutes to obtain a solution (15 mass%) containing polyimide 2.
The obtained solution was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Subsequently, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes to obtain a film of polyimide 2 having a thickness of 50 μm (error. + -. 3 μm). For the obtained film, YI, Tg and CTE were measured. The results are shown in table 1 below.
EXAMPLE 1
The polyimide solution of comparative example 1 and the polyimide solution of comparative example 2 were put in a three-necked flask and stirred at 40 ℃ for 60 minutes, whereby a polyimide solution (15 mass%) containing polyimide 1 and polyimide 2 was obtained. The resulting solution was a mixture solution of polyimide 1 and polyimide 2. In the obtained solution, the content of the polyimide 1 and the content of the polyimide 2 were 41.4 mass% and 58.6 mass%, respectively, with respect to the total amount of the polyimide 1 and the polyimide 2.
The polyimide solution thus obtained was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Subsequently, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes to obtain a film having a thickness of 50 μm (error. + -. 3 μm) of the mixture of polyimide 1 and polyimide 2. In the obtained film (mixture), the content of polyimide 1 and the content of polyimide 2 were 41.4 mass% and 58.6 mass%, respectively. For the obtained film, YI, Tg and CTE were measured. The results are shown in table 1 below.
Comparative example 3
9.84g (22 mmol) of 9, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride (BPAF), 4.21g (22 mmol) of 1,2,3, 4-cyclobutanetetracarboxylic dianhydride (CBDA), 7.51g (22 mmol) of 9, 9-bis (4-aminophenyl) fluorene (BAFL), 3.67g (22 mmol) of Isophoronediamine (IPDA), 0.23g of oxalic anhydride, 0.59g of triethylamine, 120g of N-methylpyrrolidone (NMP) and 40g of toluene were put into a three-necked flask, and after stirring at 40 ℃, the temperature of a silicone oil bath was raised to 180 ℃ and heating and stirring were carried out at 200r.p.m. for 1 hour. Heating was carried out in a silicon oil bath for removing 40ml of the water-toluene fraction, and stirring was continued in this state. The reaction was stopped after 3 hours and 30 minutes to obtain a solution (15 mass%) containing polyimide (polyimide 3) which is a copolymer of BPAF, CBDA, IPDA and BAFL.
The resulting solution was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Subsequently, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes to obtain a film of polyimide 3 having a thickness of 50 μm (error. + -. 3 μm). For the obtained film, YI, Tg and CTE were measured. The results are shown in table 1 below.
Comparative example 4
19.68g (43 mmol) of 9, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride (BPAF), 5.65g (36.6 mmol) of bis (aminomethyl) Norbornane (NBDA), 0.73g (6.4 mmol) of 1, 4-diaminocyclohexane (CHDA), 0.23g of oxalic anhydride, 0.59g of triethylamine, 120g of N-methylpyrrolidone (NMP) and 40g of toluene were put in a three-necked flask, and after stirring at 40 ℃, the temperature of a silicone oil bath was raised to 180 ℃ and heating and stirring were carried out at a rotation speed of 200r.p.m. (round-robin peroxide) for 1 hour. Heating was carried out in a silicon oil bath for removing 40ml of the water-toluene fraction, and stirring was continued in this state. Then, the reaction was stopped after 3 hours and 30 minutes to obtain a solution (15 mass%) containing polyimide 1. The polyimide 1 corresponds to the polyimide (I) described above.
The resulting solution was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Next, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes, and film formation of the coating film was attempted, but film formation was not performed.
Comparative example 5
Butane-1, 2,3, 4-tetracarboxylic dianhydride (BuDA)5.15g (26 mmol), 5- (2, 5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic dianhydride (MCHDA)2.37g (9 mmol), norbornane-2-spiro-2 ' -cyclopentanone-5 ' -spiro-2 ' -norbornane-5, 5 ', 6,6 ' -tetracarboxylic dianhydride (CpODA)3.07g (8 mmol), 9-bis (3-methyl-4-aminophenyl) fluorene (BMAFL)13.16g (35 mmol), 2, 7-diaminofluorene (2,7-FDA)1.57g (8 mmol), oxalic anhydride 0.23g, triethylamine 0.59g, N-methylpyrrolidone (NMP)120g, 3g, 5-dioxol-5 ' -cyclopentanone-5 ' -spiro-2 ' -norbornane-5 ' -5 ' -spiro-2 ' -norbornane-carboxylic dianhydride (CpODA), 3-4, 40g of toluene was charged into a three-necked flask, and after stirring at 40 ℃, the temperature of the silicone oil bath was raised to 180 ℃ and the mixture was heated and stirred at a rotation speed of 200r.p.m. for 1 hour. Heating was carried out in a silicon oil bath for removing 40ml of the water-toluene fraction, and stirring was continued in this state. The reaction was stopped after 3 hours and 30 minutes to obtain a solution (15 mass%) containing polyimide 2.
The resulting solution was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Subsequently, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes to obtain a film of polyimide 2 having a thickness of 50 μm (error. + -. 3 μm). For the obtained film, YI, Tg and CTE were measured. The results are shown in table 1 below.
EXAMPLE 2
The polyimide solution of comparative example 4 and the polyimide solution of comparative example 5 were put in a three-necked flask and stirred at 40 ℃ for 60 minutes, whereby a polyimide solution (15 mass%) containing polyimide 1 and polyimide 2 was obtained. The resulting solution was a mixture solution of polyimide 1 and polyimide 2. In the obtained solution, the content of the polyimide 1 and the content of the polyimide 2 were 62.0 mass% and 38.0 mass%, respectively, with respect to the total amount of the polyimide 1 and the polyimide 2.
The polyimide solution thus obtained was applied to a 15cm square glass plate using a doctor blade to form a coating film having a thickness of 400 μm. Subsequently, the glass plate on which the coating film was formed was placed in a heating and drying furnace set at 90 ℃ in advance, and dried for 150 minutes to obtain a film having a thickness of 50 μm (error. + -. 3 μm) of the mixture of polyimide 1 and polyimide 2. In the obtained film (mixture), the content of polyimide 1 and the content of polyimide 2 were 62.0 mass% and 38.0 mass%, respectively. For the obtained film, YI, Tg and CTE were measured. The results are shown in table 1 below.
As can be seen from table 1 above, YI of example 1, which is a mixture of the polyimide (I) and the polyimide (II), is smaller than that of comparative example 2, which is the polyimide (II) alone. Further, the heat resistance is also excellent, and the CTE is also small. It is considered that the heat resistance is excellent if Tg is 300 ℃ or higher. The polyimide of comparative example 3, which is a copolymer of the polyimide (I) and the polyimide (II), has a large YI and CTE.
EXAMPLE 3
The film of example 1 was coated with a resin emulsion (HYTEC, SN-2002, manufactured by Toho chemical Co., Ltd.) containing a conductive metal oxide using a bar coater, and then dried with hot air at 100 ℃ or lower. Thus, the film (conductive film) of example 3 having a conductive layer was obtained.
The surface resistivity and YI of the obtained film (conductive film) of example 3 were measured. The surface resistivity of the film of example 1 was also measured. The results are also shown in Table 2 below.
EXAMPLE 4
The film of example 2 was coated with a resin emulsion (HYTEC, SN-2002, manufactured by Toho chemical Co., Ltd.) containing a conductive metal oxide using a bar coater, and then dried with hot air at 100 ℃ or lower. Thus, the film (conductive film) of example 4 having a conductive layer was obtained.
The surface resistivity and YI of the obtained film (conductive film) of example 4 were measured. The surface resistivity of the film of example 2 was also measured. The results are also shown in Table 2 below.
TABLE 2
As shown in Table 2, the films of examples 3 to 4 had lower surface resistivity values than those of the films of examples 1 to 2, respectively, and the effect of conductivity was confirmed. YI is maintained or improved.
Claims (5)
1. A polyimide solution comprising: a polyimide (I) composed of a repeating unit represented by the following formula (1) and a polyimide (II) composed of a repeating unit represented by the following formula (2),
the content of the polyimide (I) is 5 to 95 mass% and the content of the polyimide (II) is 95 to 5 mass% with respect to the total amount of the polyimide (I) and the polyimide (II),
in the formula (1), A1Represents a 4-valent aromatic group having a fluorene skeleton, B1Represents a 2-valent aliphatic group or alicyclic group,
in the formula (2), A2Represents a 4-valent aliphatic group or alicyclic group, B2Represents a 2-valent aromatic group having a fluorene skeleton.
2. A polyimide which is a mixture of a polyimide (I) composed of a repeating unit represented by the following formula (1) and a polyimide (II) composed of a repeating unit represented by the following formula (2),
the content of the polyimide (I) is 5 to 95 mass%, the content of the polyimide (II) is 95 to 5 mass%,
in the formula (1), A1Represents a 4-valent aromatic group having a fluorene skeleton, B1Represents a 2-valent aliphatic group or alicyclic group,
in the formula (2), A2Represents a 4-valent aliphatic group or alicyclic group, B2Represents a 2-valent aromatic group having a fluorene skeleton.
3. The polyimide according to claim 2, wherein the glass transition temperature is 280 ℃ or higher.
4. The polyimide according to claim 2 or 3, which has a yellowness index of 3 or less.
5. A conductive film comprising a polyimide layer formed from the polyimide according to any one of claims 2 to 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-114388 | 2019-06-20 | ||
| JP2019114388 | 2019-06-20 | ||
| PCT/JP2020/023265 WO2020255890A1 (en) | 2019-06-20 | 2020-06-12 | Polyimide solution and polyimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112437786A true CN112437786A (en) | 2021-03-02 |
Family
ID=74040480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080003434.0A Pending CN112437786A (en) | 2019-06-20 | 2020-06-12 | Polyimide solution and polyimide |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP7095115B2 (en) |
| CN (1) | CN112437786A (en) |
| TW (1) | TWI783237B (en) |
| WO (1) | WO2020255890A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102333811A (en) * | 2009-03-04 | 2012-01-25 | 三井化学株式会社 | Polyamic acid and polyimide, processes for the production of same, compositions containing same, and uses thereof |
| JP2015516031A (en) * | 2012-05-11 | 2015-06-04 | アクロン ポリマー システムズ，インコーポレイテッド | Thermally stable flexible substrate for electronic devices |
| WO2016088641A1 (en) * | 2014-12-04 | 2016-06-09 | コニカミノルタ株式会社 | Polyimide film and method for manufacturing same, flexible printed wiring board, substrate for flexible display, front plate for flexible display, led illumination device, and organic electroluminescence display device |
| CN108431136A (en) * | 2015-12-28 | 2018-08-21 | 宇部兴产株式会社 | The polyimide precursor composition used in polyimide material, its manufacturing method and its manufacture |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6010533B2 (en) * | 1977-04-05 | 1985-03-18 | 株式会社日立製作所 | Molding resin composition |
| JP6791143B2 (en) * | 2015-07-31 | 2020-11-25 | 日産化学株式会社 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
| WO2019069723A1 (en) * | 2017-10-04 | 2019-04-11 | 三菱瓦斯化学株式会社 | Polyimide resin, polyimide varnish, and polyimide film |
-
2020
- 2020-06-12 JP JP2020561931A patent/JP7095115B2/en active Active
- 2020-06-12 WO PCT/JP2020/023265 patent/WO2020255890A1/en active Application Filing
- 2020-06-12 CN CN202080003434.0A patent/CN112437786A/en active Pending
- 2020-06-18 TW TW109120520A patent/TWI783237B/en active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102333811A (en) * | 2009-03-04 | 2012-01-25 | 三井化学株式会社 | Polyamic acid and polyimide, processes for the production of same, compositions containing same, and uses thereof |
| JP2015516031A (en) * | 2012-05-11 | 2015-06-04 | アクロン ポリマー システムズ，インコーポレイテッド | Thermally stable flexible substrate for electronic devices |
| WO2016088641A1 (en) * | 2014-12-04 | 2016-06-09 | コニカミノルタ株式会社 | Polyimide film and method for manufacturing same, flexible printed wiring board, substrate for flexible display, front plate for flexible display, led illumination device, and organic electroluminescence display device |
| CN108431136A (en) * | 2015-12-28 | 2018-08-21 | 宇部兴产株式会社 | The polyimide precursor composition used in polyimide material, its manufacturing method and its manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7095115B2 (en) | 2022-07-04 |
| TW202102584A (en) | 2021-01-16 |
| TWI783237B (en) | 2022-11-11 |
| JPWO2020255890A1 (en) | 2021-09-13 |
| WO2020255890A1 (en) | 2020-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20220177650A1 (en) | Polyimide film preparation method and application thereof | |
| CN113136103B (en) | Polyimide precursor resin composition | |
| CN107428934B (en) | Polyimide film, polyimide varnish, article using polyimide film, and laminate | |
| CN107949597B (en) | Polyamic acid solution composition and polyimide film | |
| KR102312462B1 (en) | Resin precursor, resin composition containing same, polyimide resin membrane, resin film, and method for producing same | |
| TWI567135B (en) | A polyimide precursor and a resin composition containing the same | |
| US7795370B2 (en) | Tetracarboxylic acid compound, polyimide thereof, and production method thereof | |
| CN101959935B (en) | Polyimide precursor composition, polyimide film and transparent flexible film | |
| JP2021102770A (en) | Polyamic acid composition with improved adhesive strength and polyimide film comprising the same | |
| CN108431086B (en) | Polyamide acid composition using alicyclic monomer and transparent polyimide film using same | |
| US20080138537A1 (en) | Low color polyimide compositions useful in optical type applications and methods and compositions relating thereto | |
| TW201734132A (en) | Polyamic acid, polyimide, polyamic acid solution, polyimide laminate, flexible device substrate, and method for producing them | |
| US20170282414A1 (en) | Flexible and transparent polyimide laminate and manufacturing method thereof | |
| JP6891084B2 (en) | Highly transparent polyimide | |
| KR102321869B1 (en) | Polyimide varnish and method for producing same | |
| CN115803365A (en) | Polyamic acid, polyamic acid solution, polyimide film, laminate, method for producing laminate, and electronic device | |
| KR102593077B1 (en) | Polyimide precursor and resin composition containing same, polyimide resin film, resin film and method of producing same | |
| CN116199883A (en) | Polyimide resin, polyimide film, preparation method and flexible equipment | |
| JP2012224755A (en) | Highly transparent polyimide precursor and resin composition using the same, polyimide molded article and method for producing the molding, plastic substrate, protective film, and electronic component and display device having the film | |
| CN112437786A (en) | Polyimide solution and polyimide | |
| CN111770949A (en) | Polyimide, polyimide solution composition, polyimide film, and substrate | |
| JP2022044020A (en) | Polyamide acid, polyamide acid solution, polyimide, polyimide film, laminate and flexible device, and method for producing polyimide film | |
| KR100792037B1 (en) | Polyamic acid photo-alignment layers and method for preparing them for liquid crystal cell | |
| CN108517035B (en) | Fluorine-containing PI film with high transparency and mechanical property and application thereof | |
| JP2013079344A (en) | Polyimide precursor, composition containing polyimide precursor, and transparent polyimide molding obtained from the composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20210302 |
|
| WD01 | Invention patent application deemed withdrawn after publication |