CN113563290A - Dianhydride monomer of polyimide resin, precursor and solution thereof - Google Patents
Dianhydride monomer of polyimide resin, precursor and solution thereof Download PDFInfo
- Publication number
- CN113563290A CN113563290A CN202110023232.9A CN202110023232A CN113563290A CN 113563290 A CN113563290 A CN 113563290A CN 202110023232 A CN202110023232 A CN 202110023232A CN 113563290 A CN113563290 A CN 113563290A
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl
- polyimide
- silicon wafer
- aromatic
- 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
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 134
- 239000002243 precursor Substances 0.000 title claims abstract description 70
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 21
- 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 title abstract description 14
- 239000000178 monomer Substances 0.000 title abstract description 8
- 239000000243 solution Substances 0.000 title description 67
- 239000004642 Polyimide Substances 0.000 claims abstract description 84
- 125000000732 arylene group Chemical group 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 77
- 229910052710 silicon Inorganic materials 0.000 claims description 77
- 239000010703 silicon Substances 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 dianhydride compound Chemical class 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 150000008378 aryl ethers Chemical group 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000000101 thioether group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000003375 sulfoxide group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001174 sulfone group Chemical group 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 22
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 46
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 44
- 238000001816 cooling Methods 0.000 description 42
- 239000012299 nitrogen atmosphere Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000001914 filtration Methods 0.000 description 28
- 238000010438 heat treatment Methods 0.000 description 28
- 239000010408 film Substances 0.000 description 24
- 238000000576 coating method Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 239000011248 coating agent Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000010954 inorganic particle Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 4
- 239000000292 calcium oxide Substances 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920005575 poly(amic acid) Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- UCQABCHSIIXVOY-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]phenoxy]aniline Chemical group NC1=CC=CC(OC=2C=CC(=CC=2)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 UCQABCHSIIXVOY-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- LVNPGQZSPDFZNC-UHFFFAOYSA-N 4-(4-amino-3-fluorophenyl)-2-fluoroaniline Chemical group C1=C(F)C(N)=CC=C1C1=CC=C(N)C(F)=C1 LVNPGQZSPDFZNC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- GTCAZWRERBLCFJ-UHFFFAOYSA-N 4-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=C(C(O)=O)C2=C1 GTCAZWRERBLCFJ-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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229920001646 UPILEX Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 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
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 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
- 230000006378 damage Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-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
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- VFFRLRQQWXGEBX-UHFFFAOYSA-N 1-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=CC2=C1 VFFRLRQQWXGEBX-UHFFFAOYSA-N 0.000 description 1
- VPSMSRGGNXFQIO-UHFFFAOYSA-N 1-aminonaphthalene-2-thiol Chemical compound C1=CC=C2C(N)=C(S)C=CC2=C1 VPSMSRGGNXFQIO-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- RPOHXHHHVSGUMN-UHFFFAOYSA-N 1-n,4-n-bis(4-aminophenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(N)=CC=2)C=C1 RPOHXHHHVSGUMN-UHFFFAOYSA-N 0.000 description 1
- SNIXNPJWOZSSEI-UHFFFAOYSA-N 2,4-diethynylaniline Chemical compound NC1=CC=C(C#C)C=C1C#C SNIXNPJWOZSSEI-UHFFFAOYSA-N 0.000 description 1
- BEBVJSBFUZVWMS-UHFFFAOYSA-N 2-(2-methylpropyl)cyclohexane-1,4-diamine Chemical compound CC(C)CC1CC(N)CCC1N BEBVJSBFUZVWMS-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical group [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
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- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
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- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/18—Bridged systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- 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
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- 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
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- 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
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- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
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- G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED
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Abstract
A dianhydride monomer, polyimide precursor resin and a solution thereof, and polyimide resin and a solution thereof. The present invention provides a tetracarboxylic acid anhydride characterized by the following general formula (1)
Description
Technical Field
The present invention relates to a dianhydride monomer for synthesizing a polyimide resin, a polyimide precursor and a solution thereof obtained by polymerizing various combinations of the dianhydride monomer or other dianhydrides with various diamines, and a polyimide resin and a solution thereof obtained by polymerizing various combinations of the dianhydride monomer or other dianhydrides with various diamines.
Background
Polyimide has excellent heat resistance, excellent mechanical performance and excellent insulating performance, and may be used widely in microelectronic and photoelectronic industry. However, conventional polyimides are typically brown or yellow materials. This is because polyimide has strong absorption in the visible light range because strong electron donors and electron acceptors exist in the molecular structure of polyimide, and a strong Charge Transfer Complex (CTC) effect is formed in or between molecular chains, causing the molecular chains to be tightly packed. This severely limits the applications of polyimides in the field of optoelectronic engineering. Therefore, in recent years, colorless and transparent polyimides that are resistant to high temperatures have been attracting much attention and research. In order to prepare the high-temperature-resistant colorless transparent polyimide, from the design of a molecular structure, a dianhydride monomer with a weak electron-withdrawing group and a diamine monomer with a weak electron-donating group are required to be selected, so that the charge transfer effect between molecular chains is reduced. For example, patent document CN103842408 discloses a polyimide oxazole resin composition, and provides a resin composition having a high transmittance. Or introducing alicyclic structure, large substituent group, strong electronegative group, asymmetric structure, rigid non-coplanar structure and the like. For example, JP2010085992 discloses a resin composition with high transmittance. However, further improvements in Tg and high temperature resistance are desired. Reference is made to patent document 1: CN 103842408; patent document 2: JP 2010085992.
In order to solve the above-mentioned problems of high transparency, high heat resistance and low Coefficient of Thermal Expansion (CTE) in combination, the present invention provides a tetracarboxylic dianhydride compound. The tetracarboxylic dianhydride compound can be used for preparing polyimide resin with higher heat resistance, low Coefficient of Thermal Expansion (CTE) and good solubility, and the polyimide resin can be applied to display devices such as flexible substrates.
Disclosure of Invention
The traditional polyimide can be used for preparing a high-temperature-resistant colorless transparent polyimide film by introducing an alicyclic structure, the alicyclic structure can destroy a conjugated structure on the chain end of the aromatic polyimide, the interaction between molecular chains is reduced, the free volume between the chains is increased, and the formation of CTC is reduced, so that the transparency of the polyimide film is improved. Further, since polyimide has poor solubility in organic solvents and thermal insolubility, and is difficult to directly mold, it is generally converted into a polyimide film by applying a polyamic acid solution containing a polyimide precursor to film formation and baking the solution. Therefore, the alicyclic structure of the bridging structure is designed, the rigidity of molecules is increased, the conjugation among chains is disturbed, and meanwhile, the solubility of the polyimide in an organic solvent is improved due to the introduction of the bridging structure, so that the polyimide is easier to mold and process.
The tetracarboxylic dianhydride provided by the invention has a structure represented by a general formula (1).
Wherein L is a single bond or is bonded with adjacent atoms to form a ring, or L is selected from one or more of arylene groups with the carbon atom number of 1-55, heteroarylene groups, alkoxy groups, alkyl sulfydryl groups, aromatic ether groups, aromatic thioether groups, straight-chain alkyl groups, branched-chain alkyl groups, alkenyl groups, alkynyl groups, naphthenic groups, heterocyclic alkyl groups and substituents with carbonyl groups. Or one or more of a sulfoxide group, an amino group with an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
From the viewpoint of simplicity of synthesis, cost and heat resistance, it is preferable that L is an arylene group, a heteroarylene oxygen atom, a sulfoxide group, a substituent having a carbonyl group.
R1 and R2 are the same or different and are respectively selected from hydrogen, deuterium, electron-withdrawing groups (including fluorine atoms, various fluorine-containing substituents, cyano groups, nitro groups, sulfonic acid groups, acyl groups, carboxyl groups and the like). One or more of an alkyl group having 1 to 55 carbon atoms, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylmercapto group, an aromatic ether group, an aromatic thioether group, an aryl group, a heteroaryl group, a carbonyl group, a carboxyl group, a substituent having a carbonyl group, an amino group, a carbamoyl group, or a silane group having 1 to 5 silicon atoms may be directly bonded to an adjacent atom or may form a ring with an adjacent atom.
R1 and R2 may be substituents on the bridge, in addition to substituents on the ring.
From the viewpoint of simplicity of synthesis and destruction of conjugation, R1, R2 are preferably H atoms, electron-withdrawing groups.
The anhydrides include steric configurations, which are also within the scope of the claims, not limited to formula (1).
The dianhydride compound of the present invention has the following general formula (2) when L is a single bond
R1 and R2 are as defined in the general formula (1). Also, the steric configuration included in the acid anhydride is not limited to the formula (2) within the scope of the present patent.
From the viewpoint of simplicity of synthesis and destruction of conjugation, R1, R2 are preferably H atoms, electron-withdrawing groups.
Next, the polyimide precursor resin prepared from the tetracarboxylic dianhydride provided by the present invention has a repeating unit represented by the following general formula (3).
Wherein X is selected from one or more of hydrogen, deuterium, alkyl with 1-18 carbon atoms, aryl, heteroaryl or alkyl silicon base.
Wherein L is a single bond or is bonded with adjacent atoms to form a ring, or L is selected from one or more of arylene groups with the carbon atom number of 1-55, heteroarylene groups, alkoxy groups, alkyl sulfydryl groups, aromatic ether groups, aromatic thioether groups, straight-chain alkyl groups, branched-chain alkyl groups, alkenyl groups, alkynyl groups, naphthenic groups, heterocyclic alkyl groups and substituents with carbonyl groups. Or one or more of a sulfoxide group, an amino group with an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
From the viewpoints of simplicity of synthesis, cost, and heat resistance, it is preferable that L is an arylene group, a heteroarylene oxygen atom, a sulfoxide group, a substituent having a carbonyl group, or the like.
R5 is selected from arylene or heteroaryl with 6-50 carbon atoms.
The steric configuration of the repeating unit is not limited to the general formula (3) and is also within the scope of the claims.
X is preferably one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms and an alkylsilyl group having 3 to 9 carbon atoms.
Further, the present invention provides a polyimide precursor resin solution containing the polyimide precursor resin represented by the general formula (3) and an organic solvent.
The polyimide resin of the present invention has a repeating unit represented by the following general formula (4).
Wherein R5 is selected from arylene or heteroaryl with 6-50 carbon atoms. L is a single bond or is bonded with adjacent atoms to form a ring, or L is selected from one or more of arylene with 1-55 carbon atoms, heteroarylene, alkoxy, alkyl sulfydryl, aromatic ether group, aromatic thioether group, straight-chain alkyl, branched-chain alkyl, alkenyl, alkynyl, naphthenic group, heterocyclic alkyl and substituent with carbonyl. Or one or more of a sulfoxide group, an amino group with an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
From the viewpoint of simplicity of synthesis, cost and heat resistance, it is preferable that L is an arylene group, a heteroarylene oxygen atom, a sulfoxide group, a substituent having a carbonyl group.
The repeating units include steric configurations, which are also within the scope of the claims, not limited to formula (4).
R5 is selected from arylene or heteroaryl with 6-50 carbon atoms.
Further, the polyimide resin solution provided by the present invention contains the polyimide resin represented by the general formula (4) and an organic solvent.
Finally, the invention provides a transparent flexible substrate which contains the polyimide material described in the general formula (4).
According to the present invention, a rigid alicyclic tetracarboxylic dianhydride can be provided; can provide a polyimide precursor resin having high solubility in an organic solvent and a solution thereof; can provide a polyimide resin having a low CTE, a high Tg and a good transparency, and a solution thereof. Further, according to the present invention, a flexible transparent substrate can be provided, which is used for a substrate material for display, a transparent base material for a touch panel, a base material for a solar cell, or the like.
The tetracarboxylic dianhydride compound is not particularly limited, and the following examples are preferred.
Detailed Description
[ Synthesis of acid anhydride ]
The tetracarboxylic dianhydride compound of the present invention is illustrated by the following examples, but is not limited to the tetracarboxylic dianhydride compound and the synthesis method of these examples. For example, a bridge is formed by Diels-Alder reaction, then addition reaction is carried out to obtain a halide, and the corresponding tetracarboxylic dianhydride is obtained by amidation, coupling reaction and deprotection. In the following reactions, M represents a Tomata-Jade coupling reaction of a magnesium compound represented by MgBr or the like, a radical-bank coupling reaction of a zinc compound represented by ZnCl or the like, a Sharpu-Right coupling reaction of a tin compound represented by SuBu3 or the like, a Juniperus coupling reaction of a silicon compound represented by Si (OH)3 or the like, and a Suzuki-Miyaura coupling reaction represented by B (OH)2 or the like, Hal represents a halogen such as a chlorine atom, a bromine atom, an iodine atom or the like, or a pseudohalogen such as trifluoromethanesulfonic acid group or the like, but is not limited to these.
[ polyimide precursor ]
The polyimide precursor of the present invention is a polyimide precursor containing at least one repeating unit represented by the general formula (34).
Wherein L is selected from one or more of aryl, heteroaryl, arylene, heteroarylene, alkoxy, alkyl sulfydryl, aromatic ether group, aromatic thioether group, straight-chain alkyl, branched-chain alkyl, alkenyl, alkynyl, naphthenic group, heterocyclic alkyl and substituent with carbonyl group, wherein the number of carbon atoms is 1-55. Or one or more of a sulfone group, an amino group having an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
Wherein R5 is selected from arylene or heteroaryl with 6-50 carbon atoms. From the viewpoint of heat resistance and solubility, one or more of the groups represented by the following general formulae (a) to (e) are preferable.
In the general formula (c), R6 and R7 are the same or different and are selected from one or more of hydrogen atoms, fluorine atoms, methyl groups, ethyl groups, hydroxyl groups, nitro groups, cyanine groups and trifluoromethyl groups.
In the general formula (d), Y is selected from the group consisting of-O-, -S-, -C (CF3) 2-, -C (CH3) 2-, -CH 2-, -O-C6H 4-C (CH3) 2-C6H 4-O-, -O-C6H 4-C (CF 2) -O-C6H 4-O-, -O-C6H 4-SO 2-C6H 42-O-, -C (CH3) 2-C6H 4-C (CH3) 2-, -O-C6H 4-C6H 4-O-, -CONH-C6H 4-HNCO-, -NHCO-C6H 4-CONH-, -C6H 5, -CONH 2, -SO 589-O-C6H 589-O-3524-O-C6H 638-O-C6H 639-O-C6H 6327-O-C6H-H5-, -CONH 3524-O-C6H-O-C6H-O-C6H-O-C6H-O-C6H-C6H-O-C6H-O-H-C6H-O-H-O-H-O-H-O-H-O-H-O-C6H-O-H-O-H-O-H-O-H-H.
R6 and R7 in the general formula (c) are preferably a hydrogen atom, a fluorine atom, a methyl group or an ethyl group from the viewpoint of heat resistance. From the viewpoint of solubility, a methyl group, a hydroxyl group or a trifluoromethyl group is preferable.
The polyimide precursor is prepared by polymerizing a tetracarboxylic acid component and diamine. The tetracarboxylic acid component is selected from the general formula (1), and the tetracarboxylic acid comprises tetracarboxylic acid, tetracarboxylic dianhydride, tetracarboxylic acid silyl ester, tetracarboxylic acid chlorine and other tetracarboxylic acid derivatives. The diamine component contains at least one aromatic ring in the chemical structure. The diamine may be one, or more types of diamines. The diamine in the present invention is not particularly limited, and the following may be mentioned: m-phenylenediamine, p-phenylenediamine, 3, 5-diaminobenzoic acid, 1, 5-naphthalenediamine, 2, 6-naphthalenediamine, 9, 10-anthracenediamine, 2, 7-diaminofluorene, 4,4 ' -diaminobenzanilide, 3,4 ' -diaminodiphenyl ether, 4-4 ' -diaminodiphenyl ether, 3-carboxy-4, 4 ' -diaminodiphenylmethane, 4,4 ' -diaminodiphenyl ether, 3-carboxy-4, 4 ' -diaminodiphenyl sulfide, 3-sulfonic acid-4, 4 ' -diaminodiphenyl sulfide, 9, 9-bis (4-aminophenyl) fluorene, 3, 3' -bis (trifluoromethyl) benzidine, p-methylenebis (phenylenediamine), 1, 3-bis (4-aminophenoxy) benzene, 1, 3-bis (3-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 2, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, 2, 2-bis (4-aminophenyl) hexafluoropropane, bis (4-aminophenyl) sulfone, 3, 3-bis ((aminophenoxy) phenyl) propane, 2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, bis (4- (4-aminophenoxy) diphenylsulfone, bis (4- (3-aminophenoxy) diphenyl) sulfone, octafluorobenzidine, 3,3 '-dimethoxy-4, 4' -diaminobiphenyl, 3,3 '-dichloro-4, 4' -diaminobiphenyl, 3,3 '-difluoro-4, 4' -diaminobiphenyl, 4,4 '-bis (4-aminophenoxy) biphenyl, 4, 4' -bis (3-aminophenoxy) biphenyl, 1, 4-diaminocyclohexylamine, 1, 4-diamino-2-methylcyclohexane, 1, 4-diamino-2-ethylcyclohexane, 1, 4-diamino-2-n-propylcyclohexane, 1, 4-diamino-2-isopropylcyclohexane, 1, 4-diamino-2-n-butylcyclohexane, 1, 4-diamino-2-isobutylcyclohexane, 1, 4-diamino-2-sec-butylcyclohexane, 1, 4-diamino-2-tert-butylcyclohexane, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, m-toluidine, 3,3 ' -dimethyl-4, 4 ' -diaminobiphenyl, 3,3 ' -dimethoxy-4, 4 ' -diaminobiphenyl, 3,3 ' -dichloro-4, 4 ' -diaminobiphenyl, 3,3 ' -difluoro-4, 4 ' -diaminobiphenyl, 3,3 ' -diaminobiphenyl, N, N ' -bis (4-aminophenyl) terephthalamide, N, N ' -p-phenylenebis (p-aminobenzoyl), 4-aminophenyl-4-aminobenzoic acid, bis (4-aminophenyl) terephthalate, bis (4-aminophenyl) biphenyl-4, 4 ' -dicarboxylic acid ester, p-phenylenebis (p-aminobenzoic acid), bis (4-aminophenyl) - [1,1 ' -biphenyl ] -4,4 ' -dicarboxylic acid ester, [1,1 ' -biphenyl ] -4,4 ' -diylbis (4-aminobenzoic acid) 4,4 ' -bis (4-aminophenoxy) biphenyl, 4,4 ' -bis (3-aminophenoxy) biphenyl, and the like, and derivatives thereof.
The method for synthesizing the polyimide precursor of the present invention is not limited, and specific examples thereof include dissolving diamine in an organic solvent, stirring while slowly adding tetracarboxylic dianhydride, and stirring at a temperature of 0 to 120 ℃, preferably 10 to 80 ℃ for 1 to 72 hours to obtain a polyimide precursor. When polymerization is carried out at 80 ℃ or higher, imidization occurs, resulting in instability of molecular weight, and a polyimide precursor cannot be stably obtained. Therefore, the temperature is preferably less than 80 ℃.
An end-capping agent may be used for the polyimide precursor. As the end-capping agent, monoamine, monoalcohol, acid anhydride, monocarboxylic acid, monoacid chloride compound, mono-active ester compound, etc. can be used. Since the use of the end-capping agent enables the molecular weight to be adjusted within a preferred range, the end-capping agent is preferably used in the preparation of the polyimide precursor.
Examples of the monoamine used as the end-capping agent include 5-amino-8-quinolinol, 4-amino-8-quinolinol, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-8-aminonaphthalene, 1-hydroxy-7-aminobenzene, 1-hydroxy-4-aminobenzene, 1-hydroxy-3-aminobenzene, 1-hydroxy-2-aminobenzene, 1-amino-7-hydroxynaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 2-hydroxy-4-aminobenzene, 2-hydroxy-4-aminonaphthalene, 2-hydroxy-3-aminonaphthalene, 1-amino-2-hydroxynaphthalene, 1-carboxy-4-aminonaphthalene, 1-carboxy-8-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 1-carboxy-4-aminonaphthalene, 1-carboxy-3-aminonaphthalene, 1-carboxy-2-aminonaphthalene, 1-amino-7-carboxynaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-carboxy-4-aminonaphthalene, 2-carboxy-3-aminonaphthalene, 1-amino-2-carboxynaphthalene, 2-aminonicotinic acid, 4-aminonicotinic acid, 5-aminonicotinic acid, 6-aminonicotinic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 3-aminoorthotoluic acid, ammelide, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 3-amino-4, 6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 5-amino-8-mercaptoquinoline, 4-amino-8-mercaptoquinoline, 1-mercapto-8-aminonaphthalene, 1-mercapto-7-aminonaphthalene, 1-mercapto-6-aminonaphthalene, 1-mercapto-5-aminonaphthalene, 1-mercapto-4-aminonaphthalene, 1-mercapto-3-aminonaphthalene, 1-mercapto-2-aminonaphthalene, 1-amino-7-mercaptonaphthalene, 2-mercapto-7-aminonaphthalene, 2-mercapto-6-aminonaphthalene, 2-mercapto-5-aminonaphthalene, 2-mercapto-4-aminonaphthalene, 2-mercapto-3-aminonaphthalene, 1-amino-2-mercaptonaphthalene, 3-amino-4, 6-dimercaptopyrimidine, 2-aminothiophenol, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 2, 4-diacetylenylaniline, 2, 5-diacetylene 2-aminonaphthalene, 1-ethynyl-3-aminonaphthalene, 1-ethynyl-4-aminonaphthalene, 1-ethynyl-5-aminonaphthalene, 1-ethynyl-6-aminonaphthalene, 1-ethynyl-7-aminonaphthalene, 1-ethynyl-8-aminonaphthalene, 2-ethynyl-1-aminonaphthalene, 2-ethynyl-7-aminonaphthalene, 2-ethynyl-8-aminonaphthalene, 3, 6-diacetylene-2-aminonaphthalene, 3, 7-diacetylene-1-aminonaphthalene, 3, 7-diacetylene-2-aminonaphthalene, 4, 8-diacetylene-1-aminonaphthalene, 4, 8-diacetylene-2-aminonaphthalene, and the like, but are not limited thereto.
The resin composition solution of the present invention. As the solvent, 2 or more of the following compounds may be used alone: polar aprotic solvents such as N-methyl-2-pyrrolidone, N-dimethylformamide, N-dimethylacetamide, sulfolane, and dimethyl sulfoxide; cyclic ester solvents such as γ -butyrolactone, γ -valerolactone, σ -valerolactone, γ -caprolactone, α -methyl- γ -butyrolactone and the like; glycol solvents such as triethylene glycol; carbonate solvents such as ethylene carbonate and propylene carbonate; ethers such as tetrahydrofuran, dioxane, propylene glycol monomethyl ether; ketones such as acetophenone, 1, 3-dimethyl-2-imidazolidinone, acetone, methyl ethyl ketone, diisobutyl ketone, diacetone alcohol and the like; esters such as ethyl acetate, propylene glycol monomethyl ether acetate, and ethyl lactate; aromatic hydrocarbons such as toluene and xylene; phenol solvents such as m-cresol, p-cresol, 3-chlorophenol, and 4-chlorophenol; solvents of general interest are also possible, for example: butyl acetate, isobutyl acetate, propylene glycol methyl acetate, and cellosolve, butyl cellosolve, ethyl cellosolve acetate, butyl cellosolve acetate, and methoxyethane, diethoxyethane, dibutyl ether, diglyme, cyclopentanone, cyclohexanone, butanol, ethanol, turpentine, mineral essential oils, naphtha-based solvents, and the like.
Inorganic particles may be added to the resin in order to improve heat resistance. Examples thereof include metal inorganic particles such as platinum, gold, palladium, silver, copper, nickel, zinc, aluminum, iron, cobalt, rhodium, ruthenium, tin, lead, bismuth and tungsten, and metal oxide inorganic particles such as silicon dioxide, titanium oxide, aluminum oxide, zinc oxide, tin oxide, tungsten oxide, calcium carbonate, barium sulfate and calcium oxide. Titanium oxide, calcium oxide, silica and the like are preferable. The shape of the inorganic particles is not particularly limited, and examples thereof include spherical, elliptical, flat, rod-like, and fibrous.
The resin composition of the present invention may contain, as required, a surfactant, an antioxidant, a filler, a dye, a pigment, a silane coupling agent and the like, a primer, a flame retardant material, a defoaming agent, a leveling agent, a flow aid, a mold release agent and the like.
[ polyimide ]
The method for producing a heat-resistant polyimide film of the present invention will be described.
The polyimide of the present invention represented by the general formula (4) corresponds to the above-mentioned general formula (3) of the polyimide precursor of the present invention
The polyimide precursor is deposited on the substrate, which may be silicon wafer, ceramic, gallium arsenide, soda-lime glass, alkali-free glass, etc., but is not limited to above. The coating method is, for example, slot die coating, spin coating, spray coating, bar coating, or the like, and the coating can be carried out by combining these methods. The coated substrate is dried using a hot plate, oven, infrared ray, vacuum chamber, heating table, or the like. Then, the film is converted into a heat-resistant polyimide film at 180 ℃ or higher and 500 ℃ or lower. Examples of the method for peeling the thin film from the substrate include hydrofluoric acid immersion, hot water immersion, and laser peeling, but are not limited to the above methods.
In addition to the thermal imidization by heat treatment as described above, the imidization of the polyimide precursor can be performed by a chemical treatment method, for example, by immersing the polyimide precursor in a solution containing a cyclization dehydrating agent such as acetic anhydride in the presence of triethylamine or pyridine. Next, the cyclizing dehydrating reagent may be put into a polyimide precursor resin solution and stirred, and then the solution may be applied to a substrate and dried to obtain a partially imidized polyimide precursor, and the partially imidized polyimide precursor may be subjected to the above-described heat treatment to obtain a polyimide film.
The solvent used for the polyimide resin of the present invention is not limited, and the solvent used for the polyimide precursor resin of the present invention can be used.
In the polyimide resin of the present invention, an antioxidant, a filler, a pigment, a dye, a silane coupling agent, etc., a primer, a flame retardant material, a defoaming agent, a leveling agent, a flow aid, a release agent, etc., may be added as required.
In the present invention, by containing the polyamic acid of the present invention of the general formula (4) and an organic solvent, a resin composition of the polyamic acid can be formed. By using the resin composition, a polyimide film containing polyamic acid contained in the resin composition is imidized.
In the present invention, inorganic particles may be added to the present resin in order to improve heat resistance. Examples thereof include inorganic particles of metals such as platinum, gold, palladium, silver, copper, nickel, zinc, aluminum, iron, cobalt, rhodium, ruthenium, tin, lead, bismuth and tungsten, and inorganic particles of metal oxides such as silica, titanium oxide, alumina, zinc oxide, tin oxide, tungsten oxide, calcium carbonate, barium sulfate and calcium oxide. Titanium oxide, calcium oxide, silica and the like are preferable. The shape of the inorganic particles is not particularly limited, and examples thereof include spherical, elliptical, flat, rod-like, and fibrous.
[ Flexible substrate ]
The polyimide resin of the present invention has excellent properties such as transparency, bending resistance, high heat resistance, etc., and has a low coefficient of linear expansion (CTE) at high temperatures, and thus can be used as a substrate material for displays, a transparent substrate for touch panels, a substrate for solar cells, etc.
The parameter performance test method comprises the following steps:
(1) viscosity measurement
The obtained resin was diluted with N-methyl-2-pyrrolidone so that the solid content concentration became 10% (wt%), and the measurement was performed at 25 ℃ using a viscometer.
(2) Determination of weight average molecular weight
The weight average molecular weight was determined in terms of polystyrene by gel permeation chromatography. As the column, TXK-GELa-2500 and a-4000 from Tosoh corporation were used, and N-methyl-2-pyrrolidone was used as a mobile phase.
(3) Production of polyimide film
The numerical solution was pressure-filtered using a 1um filter to remove foreign matters. After preheating a 6-inch silicon wafer substrate at 120 ℃ for 10 minutes, the polyimide film was produced by heating the substrate at 400 ℃ for 30 minutes in an inert oven under nitrogen gas flow. The polyimide film was peeled off from the silicon wafer. The resulting film was used for the following measurements.
(4) Determination of tensile elongation, tensile maximum stress, Young's modulus
A tensile universal material tester was used. The measurement conditions were that the width was 10mm, the grip pitch was 50mm, the test speed was 50mm/min, and the measurement number n was 10.
(5) Determination of glass transition temperature (Tg)
The test was performed under a nitrogen gas flow using a thermomechanical analyzer, and the temperature rise conditions were performed under the following conditions. The first stage is heating to 200 deg.C, removing solvent and water, the second stage is cooling to room temperature, the third stage is testing at a heating rate of 5 deg.C/min, and finally the glass transition temperature is obtained.
(6) Determination of coefficient of thermal Linear expansion (CTE)
The test was performed under a nitrogen stream using a thermal mass measuring apparatus. The temperature raising program was performed as follows. The first stage, heating to 150 deg.C, removing adsorbed water, the second stage, cooling to room temperature, and the third stage, heating at 5 deg.C/min for testing, and calculating the linear thermal expansion coefficient from 50 to 400 deg.C from the obtained TMA curve.
(7) Determination of 5% weight loss temperature (Td5)
The measurement was performed under a nitrogen stream using a thermogravimetric apparatus. The temperature raising method was performed under the following conditions. The temperature is raised to 150 ℃ in the first stage, the adsorbed water is removed, and the temperature is cooled to room temperature in the second stage. In the third stage, the temperature was measured at a temperature increase rate of 10 ℃/min, and the 5% thermogravimetric reduction temperature was determined.
(7) Transmittance test
The total light transmittance (380 nm-780 nm) was measured using a spectrophotometer.
Example 1
Under a nitrogen atmosphere, 1.08g (10mmol) of PDA1, 21.70g of NMP21 were added to the reaction vessel, and the reaction mixture was stirred at room temperature for 1 hour, to which 104.34g (10mmol) of an acid anhydride was added. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. Filtering with a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling to room temperature, peeling the obtained polyimide film from the silicon wafer, and using the film for various tests. The test results are shown in table 1.
Example 2
To a reaction vessel, 1.08g (10mmol) of PDA and 18.57g of NMP were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hour, and 313.56g (10mmol) of acid anhydride was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 3
2.00g (10mmol) of ODA and 25.38g of NMP were added to the reaction vessel under a nitrogen atmosphere, and stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 4
Under a nitrogen atmosphere, 2.00g (10mmol) of ODA, 22.24g of NMP, and 1 hour of stirring at room temperature were added to the reaction vessel, and 313.56g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃, and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 5
In a nitrogen atmosphere, TFMB3.20g (10mmol) and NMP 30.18g were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour, to which was added 104.34g (10mmol) of acid anhydride. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 6
In a nitrogen atmosphere, TFMB3.20g (10mmol) and NMP 27.06g were charged in the reaction vessel, and the mixture was stirred at room temperature for 1 hour, and 313.56g of acid anhydride (10mmol) was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 7
3.48g (10mmol) of FDA and 31.31g of NMP were added to a reaction vessel under a nitrogen atmosphere, and stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 8
3.48g (10mmol) of FDA and 28.19g of NMP were added to a reaction vessel under a nitrogen atmosphere, and stirred at room temperature for 1 hour, and 313.56g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 9
Under a nitrogen atmosphere, 1.58g (10mmol) of NDA and 23.70g of NMP were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 10
Under a nitrogen atmosphere, 1.58g (10mmol) of NDA and 20.58g of NMP were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour, and 313.56g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 11
DABAN2.27g (10mmol) and NMP 26.47g were added to the reaction vessel under nitrogen atmosphere, and stirred at room temperature for 1 hour, and 104.34g of acid anhydride (10mmol) was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 12
DABAN2.27g (10mmol) and NMP 23.34g were added to the reaction vessel under nitrogen atmosphere, and stirred at room temperature for 1 hour, and 313.56g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. Filtering with a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 13
Under a nitrogen atmosphere, 0.54g (5mmol) of PDA and 1.13g (5mmol) of DABAN were added to the reaction vessel, 24.04g of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 14
0.54g (5mmol) of PDA and 1.13g (5mmol) of DABAN were charged into a reaction vessel under a nitrogen atmosphere, 20.92g of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, and 313.56g (10mmol) of acid anhydride was added to the reaction solution. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 15
1.00g (5mmol) of ODA and 1.6g (5mmol) of TFMBA were charged into a reaction vessel under a nitrogen atmosphere, 27.76g of NMP was added, and the mixture was stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 16
Under a nitrogen atmosphere, 1.00g (5mmol) of ODA and 1.6g (5mmol) of TFMBB were charged into a reaction vessel, 24.64g of NMP was added thereto, the mixture was stirred at room temperature for 1 hour, and 313.56(10mmol) of acid anhydride was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 17
0.54g (5mmol) of PDA and 0.79g (5mmol) of NTDA0 were charged into a reaction vessel under a nitrogen atmosphere, 22.68g of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, and 104.34g (10mmol) of acid anhydride was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Example 18
0.54g (5mmol) of PDA and 0.79g (5mmol) of NTDA0 were charged into a reaction vessel under a nitrogen atmosphere, 19.56g of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, and 314.34 g (10mmol) of acid anhydride was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Comparative example 1
3.48g (10mmol) of FDA and 29.31g of NMP were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hour to add 3.84g (10mmol) of CpODA3 to the reaction solution. Stirring for 2 hours at 50 ℃, and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filtering device, coating the obtained polyimide precursor solution on a silicon wafer, heating from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
Comparative example 2
3.48g (10mmol) of FDA and 22.90g of NMP were added to the reaction vessel under a nitrogen atmosphere, and stirred at room temperature for 1 hour, and 2.27g (10mmol) of PMDA-HS was added to the reaction mixture. Stirring for 2 hours at 50 ℃ and cooling to obtain the polyimide precursor solution. And filtering by using a pressure filter device, coating the obtained polyimide precursor solution on a silicon wafer, heating the silicon wafer from room temperature to 450 ℃ in a nitrogen atmosphere for thermal imidization, cooling the silicon wafer to room temperature, and peeling the obtained polyimide film from the silicon wafer, wherein the film is used for various tests. The test results are shown in table 1.
TABLE 1
From the results shown in table 1, it can be seen that: compared with comparative examples 1 and 2, the films prepared by using the tetracarboxylic dianhydride of the present invention, which incorporates a rigid aliphatic cyclic structure having a bridged structure, exhibited a significant increase in the elastic modulus (from 2,3 and 3.1 to 5.3 and 5.2, respectively) while increasing the transmittance, and also exhibited a significant decrease in the thermal expansion coefficient and an increase in the thermal decomposition temperature from 490 to 500 degrees celsius or higher. The polyimide film prepared by the invention has higher heat resistance and lower thermal expansion coefficient, and the material with the performance is more suitable for display equipment.
According to the present invention, a polyimide resin composition having transparency and high heat resistance can be provided. The polyimide resin of the present invention has excellent properties such as transparency, bending resistance, and high heat resistance, and has a low coefficient of linear expansion (CTE) at high temperatures, and thus can be used as a substrate material for displays, a transparent substrate for touch panels, a substrate for solar cells, and the like.
While embodiments of the present invention have been described in detail, other embodiments of the present invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice in the art to which the disclosure pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.
It will be understood that the present application is not limited to the precise arrangements that have been described above and that various modifications and changes may be made without departing from the scope thereof. The scope of the application is limited only by the appended claims. The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and scope of the present application should be included.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical scope of the present invention, the technical solutions and the inventive concepts of the present invention with equivalent or modified alternatives and modifications within the technical scope of the present invention.
Claims (7)
1. A dianhydride compound characterized by: having the following general formula (1)
Wherein L is a single bond or is bonded to an adjacent atom to form a ring, or L is one or more selected from the group consisting of an arylene group having 1 to 55 carbon atoms, a heteroarylene group, an alkoxy group, an alkylmercapto group, an aromatic ether group, an aromatic thioether group, a straight-chain alkyl group, a branched alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, and a substituent having a carbonyl group, or one or more selected from a sulfone group, an amino group having an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxide group, an oxygen atom, and a sulfur atom.
R1 and R2 are the same or different and are respectively selected from hydrogen, deuterium and electron-withdrawing groups (including fluorine atoms, various fluorine-containing substituents, cyano groups, nitro groups, sulfonic acid groups, acyl groups and carboxyl groups). One or more of an alkyl group having 1 to 55 carbon atoms, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylmercapto group, an aromatic ether group, an aromatic thioether group, an aryl group, a heteroaryl group, a carbonyl group, a carboxyl group, a substituent having a carbonyl group, an amino group, a carbamoyl group, or a silane group having 1 to 5 silicon atoms may be directly bonded to an adjacent atom or may form a ring with an adjacent atom. R1 and R2 may be substituents on the bridge, in addition to substituents on the ring.
The anhydrides include steric configurations, which are also within the scope of the claims, not limited to formula (1).
3. A precursor resin of polyimide having a repeating unit represented by the following general formula (3).
Wherein X is selected from one or more of hydrogen, deuterium, alkyl with 1-18 carbon atoms, aryl, heteroaryl or alkyl silicon base.
L is selected from one or more of aryl, heteroaryl, arylene, heteroarylene, alkoxy, alkyl sulfydryl, aromatic ether group, aromatic thioether group, straight-chain alkyl, branched-chain alkyl, alkenyl, alkynyl, naphthenic group, heterocyclic alkyl and substituent with carbonyl group, wherein the number of carbon atoms is 1-55. Or one or more of a sulfone group, an amino group with an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
R5 is selected from arylene or heteroaryl with 6-50 carbon atoms,
the steric configuration of the repeating unit is not limited to the general formula (3) and is also within the scope of the claims.
4. A polyimide resin having a repeating unit represented by the following general formula (4).
Wherein L is selected from one or more of aryl, heteroaryl, arylene, heteroarylene, alkoxy, alkylmercapto, aromatic ether, aromatic thioether, straight-chain alkyl, branched-chain alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl and substituent with carbonyl with 1-55 carbon atoms. Or one or more of a sulfoxide group, an amino group with an alkyl chain, an aromatic amino group, a heteroaromatic amino group, a phosphorus oxy group, or an oxygen atom, or a sulfur atom.
R5 is selected from arylene or heteroaryl with 6-50 carbon atoms.
The repeating units include steric configurations, which are also within the scope of the claims, not limited to formula (4).
5. A polyimide precursor resin solution comprising the polyimide precursor resin according to claim 4 and an organic solvent.
6. A polyimide resin solution comprising the polyimide resin according to claim 5 and an organic solvent.
7. A flexible substrate is characterized by containing a polyimide resin having a structural repeating unit represented by general formula 4.
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CN113922608A (en) * | 2021-10-29 | 2022-01-11 | 沈阳方舟石油科技发展有限公司 | Polyimide glue-filled motor winding insulation structure and preparation method thereof |
CN113922608B (en) * | 2021-10-29 | 2023-10-20 | 沈阳方舟石油科技发展有限公司 | Polyimide glue-poured motor winding insulation structure and preparation method thereof |
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