CN106947080A - Kapton preparation compositions and preparation method thereof and the preparation method using its Kapton - Google Patents
Kapton preparation compositions and preparation method thereof and the preparation method using its Kapton Download PDFInfo
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- CN106947080A CN106947080A CN201611223753.4A CN201611223753A CN106947080A CN 106947080 A CN106947080 A CN 106947080A CN 201611223753 A CN201611223753 A CN 201611223753A CN 106947080 A CN106947080 A CN 106947080A
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- preparation
- polyimide precursor
- double
- anhydride
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims description 19
- 239000004642 Polyimide Substances 0.000 claims abstract description 26
- 229920001721 polyimide Polymers 0.000 claims abstract description 26
- 239000002243 precursor Substances 0.000 claims abstract description 24
- 229920005575 poly(amic acid) Polymers 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 29
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 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 claims description 23
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 21
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 20
- 239000003431 cross linking reagent Substances 0.000 claims description 19
- -1 myristyl succinyl Chemical group 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000004952 Polyamide Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 230000009267 minimal disease activity Effects 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- JPZRPCNEISCANI-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F JPZRPCNEISCANI-UHFFFAOYSA-N 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical class COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 2
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 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
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 150000004040 pyrrolidinones Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000006091 1,3-dioxolane group Chemical class 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- FXGQUGCFZKMIJW-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-diamine Chemical compound NC1=C(F)C(N)=C(F)C(F)=C1F FXGQUGCFZKMIJW-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- FYYLCPPEQLPTIQ-UHFFFAOYSA-N 2-[2-(2-propoxypropoxy)propoxy]propan-1-ol Chemical compound CCCOC(C)COC(C)COC(C)CO FYYLCPPEQLPTIQ-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- GBBHWGRJHHNAGT-UHFFFAOYSA-N 3-hexadecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC1CC(=O)OC1=O GBBHWGRJHHNAGT-UHFFFAOYSA-N 0.000 description 1
- ZJFCVUTYZHUNSW-UHFFFAOYSA-N 3-octadecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1CC(=O)OC1=O ZJFCVUTYZHUNSW-UHFFFAOYSA-N 0.000 description 1
- BZECBEKZECEQRI-UHFFFAOYSA-N 3-tetradecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCC1CC(=O)OC1=O BZECBEKZECEQRI-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- BBTGUNMUUYNPLH-UHFFFAOYSA-N 5-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 BBTGUNMUUYNPLH-UHFFFAOYSA-N 0.000 description 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 1
- YKUPYLMLOKXQEN-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)O.[O] Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)O.[O] YKUPYLMLOKXQEN-UHFFFAOYSA-N 0.000 description 1
- GCOSNZKQRIRCBA-UHFFFAOYSA-N COC(COCCOCCOCCOC)C Chemical compound COC(COCCOCCOCCOC)C GCOSNZKQRIRCBA-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- QQQCWVDPMPFUGF-ZDUSSCGKSA-N alpinetin Chemical compound C1([C@H]2OC=3C=C(O)C=C(C=3C(=O)C2)OC)=CC=CC=C1 QQQCWVDPMPFUGF-ZDUSSCGKSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012936 correction and preventive action Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013456 study Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The preparation method of Kapton the present invention relates to polyimide precursor and preparation method thereof and using the polyimide precursor.
Description
Technical field
The present invention relates to Kapton preparation compositions comprising polyimide precursor and preparation method thereof with
And the preparation method of the Kapton using the polyimide precursor.
Background technology
The heat-resistant quality and chemical resistance of polyimides raw material are outstanding, be it is a kind of can as flexible display substrate use
On the way come the high raw material of the possibility being applicable.
Polyimide substrate raw material generally using applicator (applicator) or flat painting machine by polyamic acid (PAA,
Polyamic acid) it is coated in after slide (carrier glass), by the hot imide reaction of high temperature, it is prepared into thin
Sheet type.However, by the process rather than series-operation of batch-type (batch type), can be carried out in convection constant temperature baking oven
The output of curing process (that is, hot-imide process) is limited, and the process grown is needed very much because of more than 400 DEG C of high-temperature process
Time.
For the production capacity (CAPA, capacity) depending on the curing process carried out in convection constant temperature baking oven,
In order to improve process speed, at a high temperature of more than 120 DEG C that baking oven is not cooled down completely, it is put into coated substrate to carry out heat
Imidizate.Now, the homogenizing of film surface (leveling) characteristic is caused to be reduced because solvent rapidly volatilizees.Thus, it is
Improve this problem using crosslinking agent and carry out many correlative studys (Korean granted patent the 10-0889910th).
The content of the invention
The present invention uses the polyamides of the crosslinking agent comprising certain content to solve above-mentioned produced problem in the prior art
Imines presoma, even if the imidizate performed at high temperature, can also improve the characteristic on Kapton surface, so as to complete
The present invention.
One embodiment of the present invention provides the preparation method of polyimide precursor, and it includes：Including diamine monomer
Polymer solvent in addition acid anhydride (anhydride) monomer to be reacted the step of；End-capping reagent is added in above-mentioned reaction solution
The step for carrying out synthesizing polyamides acid is reacted after (end capping agent)；And added in above-mentioned polyamic acid
The step of crosslinking agent is to be mixed.
Another embodiment of the present invention provides the preparation method of Kapton, and it includes：Including diamine monomer
Polymer solvent in addition anhydride monomer to be reacted the step of；Reacted in above-mentioned reaction solution after addition end-capping reagent
Carry out the step of synthesizing polyamides acid；The step of crosslinking agent is to be mixed is added in above-mentioned polyamic acid；It will include and be added with
The composition of the polyamic acid of above-mentioned crosslinking agent is coated in the step on carrier；And more than 100 DEG C at a temperature of, to coating
The step of polyimide precursor on above-mentioned carrier carries out hot-imide.
The polyimide precursor of the present invention is that the crosslinking agent of certain content is added to formed by polyamic acid, even if
It can also improve the surface characteristic of Kapton in the imidizate of high temperature.Especially, the table of Kapton can be improved
Homogenizing (levelling) characteristic in face, and transmitance loss can be reduced.
Brief description of the drawings
Fig. 1 is the image of the Kapton of one embodiment of the invention.
Fig. 2 is the image of the Kapton of one embodiment of the invention.
Fig. 3 is the image of the Kapton of one embodiment of the invention.
Fig. 4 is the image of the Kapton of the comparative example of the present invention.
Fig. 5 is the image of the Kapton of the comparative example of the present invention.
Fig. 6 is the image of the Kapton of the comparative example of the present invention.
Fig. 7 is the image of the Kapton of the comparative example of the present invention.
Embodiment
Hereinafter, the example and embodiment of the present invention are described in detail referring to the drawings, in order to skill belonging to the present invention
The those of ordinary skill in art field can easily implement.
But, the present invention can be realized with a variety of different forms, be not limited to example described herein and embodiment.And
And, in order to clearly state the present invention, the part unrelated with explanation is eliminated in figure, in the specification, for similar
Part, is labelled with similar reference.
One embodiment of the present invention provides the preparation method of polyimide precursor, and it includes：Including diamine monomer
Polymer solvent in addition anhydride monomer to be reacted the step of；End-capping reagent (end capping are added in above-mentioned reaction solution
Agent the step for carrying out synthesizing polyamides acid is reacted after)；And add crosslinking agent in above-mentioned polyamic acid to be mixed
The step of conjunction.
In the example of the present invention, above-mentioned diamine monomer can be included and is selected from by p-phenylenediamine (PPDA, p-
Phenylenediamine), 4,4- diaminodiphenyl ethers (ODA, 4,4'-Oxydianiline), 4,4- MDAs
Tolidine (2,2'- dimethyl -4,4'- benzidine) (4,4'- between (MDA, 4,4'-Methylenedianiline), m-
(2,2'-Dimethyl-4,4'-Diaminobiphenyl)), 1,3- double (4'- amino-benzene oxygens) benzene (TPE-R, 1,3-BIS
(4'-Aminophenoxyl) benzene), double (trifluoromethyl) benzidine of 2,2'-) (TFMB, 2,2'-Bis
(trifluoromethyl) benzidine), double [4- (4- amino-benzene oxygens) phenyl] HFC-236fa (HFBAPP, 2,2- of 2,2-
BIS [4- (4-Aminophenoxy) Phenyl] Hexafluoropropane), double (3- amino-4-hydroxylphenyls) hexafluoros of 2,2-
Propane (BIS-AP-AF, 2,2-Bis (3-amino-4-hydroxyphenyl) hexafluoropropane), 1,3- diaminourea
2,4,5,6- phenyl tetrafluorides (DRFB, 1,3-Diamino 2,4,5,6-Tetrafluorobenzene), 3,3'- diaminodiphenylsulfones
(DDS, 3,3'-Diaminodiphenyl Sulfone), 4,4'- diaminodiphenylsulfones (ASD, 4,4'-Diaminodiphenyl
Sulfide), double [4- (4- amino-benzene oxygens) phenyl] sulfone (BAPS, Bis [4- (4-aminophenoxy) phenyl]
Sulfone), double [4- (3- amino-benzene oxygens) benzene] sulfones of 2,2-) (mBAPS, 2,2-Bis [4- (3-Aminophenoxy)
Benzene] Sulfone) and combinations thereof composition group in composition, can preferably be p-phenylenediamine (PPDA).It is above-mentioned
P-phenylenediamine (PPDA) is the monomer of aromatic structure, it is possible to provide high heat-resistant quality.
In the example of the present invention, above-mentioned anhydride monomer can be aromatic dianhydride monomer, be selected from for example, can include by 3,
3', 4,4'- benzophenone tetracarboxylic dianhydrides (BTDA, 3,3', 4,4'-benzopheno
Netetracarboxylicdianhydride), pyromellitic acid anhydride (PMDA, pyromellit icdianhydride),
3,3', 4,4'- biphenyl tetracarboxylic dianhydrides (BPDA, 3,3', 4,4'-biphenyl
Tetracarboxylicaciddianhydride), double (3,4- dicarboxylic acids) hexafluoropropane dianhydride (6FDA, 2,2-bis of 2,2'-
(3,4anhydrodicarboxyphenyl)-hexafluoropropanedi anhydride), a- biphenyl tetracarboxylic dianhydrides
The double phthalic acids of (a-BPDA, 2,3,3', 4biphenyl tetracar boxylicaciddianhydride), 4,4'- oxygen
Acid anhydride (ODPA, 4,4'-oxydi phthalic anhydride), 3,3', 4,4'- diphenyl sulfone tetrabasic carboxylic acid dicarboxylic anhydrides (DSDA, 3,
3', 4,4'-diphenylsulfone-tetracarboxylic dianhydride), double [4 (the 3,4- dicarboxyl benzene oxygen of 2,2-
Base) phenyl] propane dianhydride) (BPADA, 2,2-bis [4 (3,4-dicarboxyphenoxy) phenyl] propane
Dianhydride), the anhydride phthalic acid of quinhydrones two (HQDA, hydro quinone diphthalic anhydride) and their group
Composition in the group being combined into.More than one can be used in above-mentioned aromatic dianhydride monomer, for example, at least two monomers can be used.
In the example of the present invention, above-mentioned polymer solvent, as long as the solvent used in the art, it is possible to it is unrestricted
Use to system, be selected from for example, can include by acid amides series solvent, ketone series solvent, ether series solvent, ester series solvent, symmetrical ethylene glycol two
Composition in the group of ether solvent, ether solvent and combinations thereof composition.Above-mentioned acid amides series solvent can include dimethyl formyl
Amine (DMF), dimethylacetylamide (DMAC), n- methyl pyrrolidones (NMP) etc., above-mentioned ketone series solvent can include acetone, methyl
Ethyl ketone (MEK), methyl iso-butyl ketone (MIBK) (MIBK), cyclopentanone, cyclohexanone etc..Above-mentioned ether series solvent can include tetrahydrofuran
(THF), DOX and Isosorbide-5-Nitrae-dioxane etc., above-mentioned ester series solvent can include methyl acetate, ethyl acetate, acetic acid fourth
Ester, gamma-butyrolacton, α-acetic acid lactone, beta-propiolactone, δ-valerolactone etc..The above-mentioned ether solvent of symmetrical ethylene glycol two can include first
Ethyl glycol monomethyl ether (1,2- dimethoxy-ethanes), methyl diglycol dimethyl ether (double (2- methoxy ethyls) ethers), methyl three
Glyme (double (2- methoxy ethoxies) ethane of 1,2-), methyl tetraethylene glycol dimethyl ether (double [2- (2- methoxy ethoxies
Ethyl)] ether), ethohexadiol monomethyl ether (1,2- dimethoxy-ethanes), ethyl diglyme (double (2- ethyoxyl second
Base) ether), butyldiglycol dimethyl ether (double (2- butoxyethyl groups) ethers) etc., above-mentioned ether solvent can comprising the ethers of ethylene glycol two,
Dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol n-propyl ether, DPG n- propyl ether, propane diols n- butyl ether, DPG n-
Butyl ether, tripropylene glycol n- propyl ether, propane diols phenyl ether, dimethyl ether, 1,3- dioxolanes, ethylene glycol monobutyl ether, two
Ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, ethylene glycol monoethyl ether etc..Above-mentioned polymer solvent is preferably used more than one molten
Agent, for example, can be used n- methyl pyrrolidones (NMP).
In the example of the present invention, above-mentioned end-capping reagent uses for telo merization, and acid anhydride form can be used
Monomer.The monomer of above-mentioned acid anhydride form, for example, may be selected from by phthalic anhydride (PA, phthallic anhydride), myristyl butanedioic acid
Acid anhydride (TSA, tetradecyl succinic anhydride), cetyl succinyl oxide (HAS, hexadecyl succinic
Anhydride), octadecylsuccinic acid acid anhydride (OSA, octadecyl succinic anhydride) and combinations thereof composition
Group in, it is preferable that can be phthalic anhydride (PA).Above-mentioned end-capping reagent adjusts the molecular weight of polymer with list-acid anhydride form, reduces not anti-
The content of thing is answered, and improves keeping stability.
In the example of the present invention, it may also include the steps of：Synthesize after above-mentioned polyamic acid, addition conforms to prepare
Product benchmark solid and the step of solvent in order to adjust viscosity.Above-mentioned solvent can be used and above-mentioned synthetic identical
Solvent, in order to improve physical property, it is also possible to use other kinds of solvent.
In the example of the present invention, above-mentioned crosslinking agent can include 4,4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-).On
It is preferably 4,4 '-di-2-ethylhexylphosphine oxide (N, N- diglycidylaniline) with below formula to state crosslinking agent：
In the example of the present invention, relative to monomer, the above-mentioned crosslinking agent of about 2000 to about 4000ppm amount can be added.
When above-mentioned crosslinking agent with less than 2000ppm content add when, the surface of Kapton can be bad, when with more than
During 4000ppm content addition, the transmitance of Kapton can be reduced.
Another embodiment of the present invention provides the preparation method comprising the polyimide precursor by the application and prepared
Obtained by polyimide precursor Kapton preparation compositions.
In the example of the present invention, above-mentioned polyimide precursor can include polyamic acid polymer morphology.
In the example of the present invention, above-mentioned polyimide precursor is that the crosslinking agent of certain content is added into polyamic acid
Formed by, the imidizate even in high temperature can also improve the surface characteristic of Kapton.Especially, polyamides can be improved
Homogenizing (leve lling) characteristic on the surface of imines film, and transmitance loss can be reduced.
Another embodiment of the invention provides the preparation method of Kapton, and it includes：Including diamine monomer
Polymer solvent in addition anhydride monomer to be reacted the step of；Reacted in above-mentioned reaction solution after addition end-capping reagent
Carry out the step of synthesizing polyamides acid；The step of crosslinking agent is to be mixed is added in above-mentioned polyamic acid；It will include and be added with
The composition of the polyamic acid of above-mentioned crosslinking agent is coated in the step on carrier；And more than 100 DEG C at a temperature of, to coating
The step of polyimide precursor on above-mentioned carrier carries out hot-imide.
In the example of the application, above-mentioned hot-imide for example can be in about 100 DEG C to about 500 DEG C, about 100 DEG C to about
400 DEG C, about 100 DEG C to about 300 DEG C, about 100 DEG C to about 200 DEG C, about 200 DEG C to about 500 DEG C, about 300 DEG C to about 500 DEG C, about
Performed at 400 DEG C to about 500 DEG C, it is likely that being not limited to this.
Hereinafter, further illustrated by embodiments of the invention, the scope of the present invention is not limited to the present embodiment.
[embodiment]
Embodiment 1
In the 529.2g n- methyl pyrrolidones (NMP) of normal temperature are maintained, 21.62g (0.2mol) pair is completely dissolved
After phenylenediamine (PPDA), successively put into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides (BPDA) and
4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, putting into 0.43g
The phthalic anhydride (PA) of (0.0029mol), reaction polymerize for 16 hours to terminate polyamic acid (PAA).Then, be up to monomer (PPDA,
BPDA and PMDA) 2000ppm 4,4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-) (0.15874g) of content is dissolved in phase
After reaction dissolvent n- methyl pyrrolidones (NMP), it is added to above-mentioned polyamic acid (PAA) to be mixed.
Embodiment 2
Maintain normal temperature 529.2g n- methyl pyrrolidones (NMP) in, addition 21.62g (0.2mol) to benzene two
Amine (PPDA) puts into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides come after being completely dissolved successively
(BPDA) and 4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, input
0.43g (0.0029mol) phthalic anhydride (PA).After reaction 16 hours, monomer (PPDA, BPDA and PMDA) content is up to
(the ring propoxyl group aniline of N, N- bis-) (0.23811g) is dissolved in same reaction solvent n- methyl for the 4,4 ' of 3000ppm-di-2-ethylhexylphosphine oxide
After pyrrolidones (NMP), it is put into above-mentioned polyamic acid (PAA) to add mixing.
Embodiment 3
In the 529.2g n- methyl pyrrolidones (NMP) of normal temperature are maintained, 21.62g (0.2mol) pair is completely dissolved
After phenylenediamine (PPDA), successively put into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides (BPDA) and
4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, putting into 0.43g
The phthalic anhydride (PA) of (0.0029mol).After reaction 16 hours, the 4000ppm of monomer (PPDA, BPDA and PMDA) content is up to
4,4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-) (0.31748g) is dissolved in after solvent, be put into reaction terminate
Polyamic acid (PAA) adds mixing.
Comparative example 1
In the 529.2g n- methyl pyrrolidones (NMP) of normal temperature are maintained, 21.62g (0.2mol) pair is completely dissolved
After phenylenediamine (PPDA), successively put into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides (BPDA) and
4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, putting into 0.43g
The phthalic anhydride (PA) of (0.0029mol), reaction polymerize for 16 hours to terminate polyamic acid (PAA).Then will be same as Example 1
The solvent n- methyl pyrrolidones (NMP) of amount are put into the above-mentioned polyamic acid (PAA) of reaction end to add mixing.
Comparative example 2
Maintain normal temperature 529.2g n- methyl pyrrolidones (NMP) in, addition 21.62g (0.2mol) to benzene two
Amine (PPDA) puts into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides come after being completely dissolved successively
(BPDA) and 4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, input
0.43g (0.0029mol) phthalic anhydride (PA), reaction polymerize for 16 hours to terminate polyamic acid (PAA).Then it is up to monomer
The 1000ppm of (PPDA, BPDA and PMDA) content 4,4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-) (0.07937g) is molten
Solution is put into above-mentioned polyamic acid (PAA) to be mixed after same reaction solvent n- methyl pyrrolidones (NMP).
Comparative example 3
Maintain normal temperature 529.2g n- methyl pyrrolidones (NMP) in, addition 21.62g (0.2mol) to benzene two
Amine (PPDA) puts into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides come after being completely dissolved successively
(BPDA) and 4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, input
0.43g (0.0029mol) phthalic anhydride (PA), reaction polymerize for 16 hours to terminate polyamic acid (PAA).Then it is up to monomer
The 1500ppm of (PPDA, BPDA and PMDA) content 4,4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-) (0.119055g)
It is dissolved in after same reaction solvent n- methyl pyrrolidones (NMP), is put into above-mentioned polyamic acid (PAA) to be mixed.
Comparative example 4
Maintain normal temperature 529.2g n- methyl pyrrolidones (NMP) in, addition 21.62g (0.2mol) to benzene two
Amine (PPDA) puts into 52.96g (0.18mol) 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides come after being completely dissolved successively
(BPDA) and 4.36g (0.02mol) pyromellitic acid anhydride (PMDA).Etc. be completely dissolved and by after 1 hour, input
0.43g (0.0029mol) phthalic anhydride (PA).After reaction 16 hours, monomer (PPDA, BPDA and PMDA) content is up to
(the ring propoxyl group aniline of N, N- bis-) (0.39685g) is dissolved in same reaction solvent n- methyl for the 4,4 ' of 5000ppm-di-2-ethylhexylphosphine oxide
After pyrrolidones (NMP), it is put into the polyamic acid (PAA) of reaction end to add mixing.
Experimental example 1
Using applicator (Baker applicator), with 400 μm of wet films (wet) thickness, by embodiment 1 to embodiment
3 and the polyimide precursor of comparative example 1 to comparative example 4 be coated in LCD Glass SM TECH, new glass (200*200*
0.63) after, it is put into the convection constant temperature baking oven of 120 DEG C of heating to carry out hot imide reaction.Then, heating 3 per minute
DEG C, Slow cooling after being maintained 1 hour under maximum 450 DEG C.Reclaimed after cooling, analysed film formalness and optics are special
Property etc., and the results are shown in Fig. 1 to Fig. 4 and table 1 and table 2.
Table 1
Table 2
As shown in Figures 1 to 7, confirm as addition 2000ppm to the 4 of 4000ppm contents, 4 '-di-2-ethylhexylphosphine oxide (N, N-
Two ring propoxyl group aniline) when (Fig. 1 to Fig. 3), the homogenizing of film surface is in good condition, but is not added with 4,4 '-di-2-ethylhexylphosphine oxide (N,
The ring propoxyl group aniline of N- bis-) when (Fig. 4) and when being added with 1000ppm or 5000ppm content (Fig. 5 to Fig. 7), film surface
Homogenizing state is bad.
Also, as shown in table 1 and table 2, confirm when addition is less than 2000ppm or more than 5000ppm, transmitance
Rapid reduction.
Above-mentioned explanation of the invention is used to illustrate, and general technical staff of the technical field of the invention is appreciated that
In the case of the technological thought or essential feature that do not change the present invention, it can be easily deformed with different specific forms.Therefore,
The multiple embodiments for being interpreted as above description are exemplary, and non-limiting in all respects.For example, illustrated with single type
Each structural element can also dispersedly be implemented, equally, and the multiple structural elements for disperseing explanation also can be real with the form of combination
Apply.
Range Representation, rather than above-mentioned detailed description is claimed by appended invention in the scope of the present invention, and invention will
The form for asking the implication and scope of protection domain and having altered or deform derived from its equivalents should be interpreted bag
Include in the scope of the present invention.
Claims (10)
1. a kind of polyimide precursor composition, it is characterised in that include：
Polyamic acid；And
Crosslinking agent, the content relative to polyamic acid is 2000 to 4000ppm.
2. the preparation method of polyimide precursor according to claim 1, it is characterised in that above-mentioned diamine monomer is selected from
By double (the 4'- aminobenzenes of tolidine, 1,3- between p-phenylenediamine, 4,4- diaminodiphenyl ethers, 4,4- MDAs, m-
Epoxide) benzene, double (trifluoromethyl) benzidine of 2,2'-), double [4- (4- amino-benzene oxygens) phenyl] HFC-236fas of 2,2-), 2,2- it is double
(3- amino-4-hydroxylphenyls) HFC-236fa, 1,3- diaminourea 2,4,5,6- phenyl tetrafluorides, 3,3'- diaminodiphenylsulfones, 4,4'-
Double [4- (3- amino-benzene oxygens) benzene] sulfones of diaminodiphenylsulfone, double [4- (4- amino-benzene oxygens) phenyl] sulfones, 2,2-) and they
In the group for combining composition.
3. the preparation method of polyimide precursor according to claim 1, it is characterised in that above-mentioned anhydride monomer is fragrance
Race's dianhydride monomer.
4. the preparation method of polyimide precursor according to claim 3, it is characterised in that above-mentioned aromatic dianhydride list
Body, which is included, to be selected from by 3,3', 4,4'- benzophenones tetracarboxylic dianhydride, pyromellitic acid anhydride, 3,3', 4,4'- biphenyl tetracarboxylic dianhydrides,
Double (3,4- dicarboxylic acids) hexafluoropropane dianhydrides of 2,2'-, a- biphenyl tetracarboxylic dianhydrides, 4,4'- oxygen double phthalic anhydride, 3,3',
Double [4 (3,4- di carboxyl phenyloxies) phenyl] propane dianhydrides of 4,4'- diphenyl sulfone tetrabasic carboxylic acids dicarboxylic anhydride, 2,2-), the phthalandione of quinhydrones two
Composition in the group of acid anhydride and combinations thereof composition.
5. the preparation method of polyimide precursor according to claim 1, it is characterised in that addition at least two acid anhydride list
Body.
6. the preparation method of polyimide precursor according to claim 1, it is characterised in that above-mentioned polymer solvent is included
Selected from by acid amides series solvent, ketone series solvent, ether series solvent, ester series solvent, the ether solvent of symmetrical ethylene glycol two, ether solvent and it
Combination composition group in composition.
7. the preparation method of polyimide precursor according to claim 1, it is characterised in that above-mentioned end-capping reagent be selected from by
The group that phthalic anhydride, myristyl succinyl oxide, cetyl succinyl oxide, octadecylsuccinic acid acid anhydride and combinations thereof are constituted
In.
8. the preparation method of polyimide precursor according to claim 1, it is characterised in that above-mentioned crosslinking agent includes 4,
4 '-di-2-ethylhexylphosphine oxide (the ring propoxyl group aniline of N, N- bis-).
9. the preparation method of polyimide precursor according to claim 1, it is characterised in that whole relative to used
Body monomer, the above-mentioned crosslinking agent of the amount of addition 2000 to 4000ppm.
10. a kind of preparation method of Kapton, it is characterised in that including：
The step of anhydride monomer is to be reacted is added in the polymer solvent comprising diamine monomer；
The step for carrying out synthesizing polyamides acid is reacted after end-capping reagent is added in answering solution；
The step of crosslinking agent is to be mixed is added in above-mentioned polyamic acid；
Composition comprising the polyamic acid added with above-mentioned crosslinking agent is coated in the step on carrier；And
At a temperature of more than 100 DEG C, the step of hot-imide is carried out to the polyimide precursor being coated on above-mentioned carrier
Suddenly.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2015-0190977 | 2015-12-31 | ||
| KR1020150190977A KR102531268B1 (en) | 2015-12-31 | 2015-12-31 | Polyimideprecursor, method for producing thereof and method for producing polyimide film using the same |
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| Publication Number | Publication Date |
|---|---|
| CN106947080A true CN106947080A (en) | 2017-07-14 |
| CN106947080B CN106947080B (en) | 2024-02-23 |
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| JP (1) | JP6928447B2 (en) |
| KR (1) | KR102531268B1 (en) |
| CN (1) | CN106947080B (en) |
| TW (1) | TWI739784B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109384922A (en) * | 2017-08-11 | 2019-02-26 | 东进世美肯株式会社 | The preparation method of polyimide precursor composition and the polyimide film using it |
| CN109384921A (en) * | 2017-08-11 | 2019-02-26 | 东进世美肯株式会社 | The preparation method of polyimide precursor composition and the polyimide film using it |
| CN112585228A (en) * | 2018-08-22 | 2021-03-30 | Pi尖端素材株式会社 | Polyimide varnish for coating conductor containing aromatic carboxylic acid and method for producing same |
Families Citing this family (7)
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|---|---|---|---|---|
| KR101906394B1 (en) * | 2017-11-10 | 2018-10-11 | 에스케이씨코오롱피아이 주식회사 | Ultra Thin Black Polyimide Film and Method For Preparing The Same |
| KR102491338B1 (en) * | 2018-01-26 | 2023-01-27 | 주식회사 넥스플렉스 | flexible metal clad laminate and THERMOPLASTIC POLYIMIDE PRECORSOR COMPOSITION for flexible metal clad laminate |
| KR102141893B1 (en) * | 2018-04-05 | 2020-08-07 | 피아이첨단소재 주식회사 | Polyimide Film for Preparing Flexible Metal Foil Clad Laminate And Flexible Metal Foil Clad Laminate Comprising the Same |
| KR102141892B1 (en) * | 2018-04-05 | 2020-08-07 | 피아이첨단소재 주식회사 | Polyimide Film for Preparing Flexible Metal Foil Clad Laminate And Flexible Metal Foil Clad Laminate Comprising the Same |
| WO2020166913A1 (en) * | 2019-02-14 | 2020-08-20 | 주식회사 엘지화학 | Polyimide precursor composition and polyimide film manufactured using same |
| KR102362385B1 (en) * | 2019-11-13 | 2022-02-15 | 피아이첨단소재 주식회사 | High Elastic and High Heat Resistant Polyimide Film and Manufacturing Method Thereof |
| KR20240053229A (en) * | 2022-10-17 | 2024-04-24 | 피아이첨단소재 주식회사 | Polyimide film and manufacturing method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030121844A1 (en) * | 2001-11-06 | 2003-07-03 | Koo Ja-Young | Selective membrane having a high fouling resistance |
| CN1468649A (en) * | 2002-07-16 | 2004-01-21 | 世韩工业株式会社 | Method for producing selective diffusion barrier with excellent pollution resistibility |
| KR20070113631A (en) * | 2006-05-25 | 2007-11-29 | 주식회사 엘지화학 | Method for preparing porous polyimide film using polymer nano-particles and porous polyimide film prepared by the same method |
| JP2009102494A (en) * | 2007-10-23 | 2009-05-14 | Chisso Corp | Composition for use in screen printing |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11305031A (en) * | 1998-02-20 | 1999-11-05 | Toray Ind Inc | Color filter and liquid crystal display device |
| JP2004123857A (en) * | 2002-10-01 | 2004-04-22 | Teijin Ltd | Polyamic acid composition and process for preparing polyamic acid |
| JP4074987B2 (en) * | 2002-10-29 | 2008-04-16 | 東レ・デュポン株式会社 | Polyimide film and stiffener for flexible circuit board using the same |
| KR101225842B1 (en) * | 2007-08-27 | 2013-01-23 | 코오롱인더스트리 주식회사 | Colorless polyimide film |
| JP5577591B2 (en) * | 2007-12-27 | 2014-08-27 | Ｊｎｃ株式会社 | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element |
| TWI445765B (en) * | 2009-06-09 | 2014-07-21 | Asahi Kasei E Materials Corp | A resin composition, a cured product, and a circuit substrate using the same |
| KR101543478B1 (en) * | 2010-12-31 | 2015-08-10 | 코오롱인더스트리 주식회사 | Transparent Polyimide film and Method for Preparing the Same |
| JP2012184281A (en) * | 2011-03-03 | 2012-09-27 | Hitachi Chemical Dupont Microsystems Ltd | Resin composition |
| KR102058760B1 (en) * | 2011-10-10 | 2019-12-23 | 브레우어 사이언스 인코포레이션 | Spin-on carbon compositions for lithographic processing |
| JP5939066B2 (en) * | 2011-11-15 | 2016-06-22 | Jsr株式会社 | Method for producing liquid crystal aligning agent |
| JP6206071B2 (en) * | 2013-10-15 | 2017-10-04 | 東レ株式会社 | RESIN COMPOSITION, POLYIMIDE RESIN FILM USING THE SAME, COLOR FILTER CONTAINING THE SAME, TFT SUBSTRATE, DISPLAY DEVICE AND METHOD FOR PRODUCING THEM |
-
2015
- 2015-12-31 KR KR1020150190977A patent/KR102531268B1/en active IP Right Grant
-
2016
- 2016-12-27 CN CN201611223753.4A patent/CN106947080B/en active Active
- 2016-12-28 JP JP2016255918A patent/JP6928447B2/en active Active
- 2016-12-30 TW TW105144096A patent/TWI739784B/en active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030121844A1 (en) * | 2001-11-06 | 2003-07-03 | Koo Ja-Young | Selective membrane having a high fouling resistance |
| CN1468649A (en) * | 2002-07-16 | 2004-01-21 | 世韩工业株式会社 | Method for producing selective diffusion barrier with excellent pollution resistibility |
| KR20070113631A (en) * | 2006-05-25 | 2007-11-29 | 주식회사 엘지화학 | Method for preparing porous polyimide film using polymer nano-particles and porous polyimide film prepared by the same method |
| JP2009102494A (en) * | 2007-10-23 | 2009-05-14 | Chisso Corp | Composition for use in screen printing |
Non-Patent Citations (1)
| Title |
|---|
| XAVIER JD ET AL: "Plasticization Suppression in Grafted Polyimide−Epoxy Network Membranes", 《IND.ENG.CHEM.RES》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109384922A (en) * | 2017-08-11 | 2019-02-26 | 东进世美肯株式会社 | The preparation method of polyimide precursor composition and the polyimide film using it |
| CN109384921A (en) * | 2017-08-11 | 2019-02-26 | 东进世美肯株式会社 | The preparation method of polyimide precursor composition and the polyimide film using it |
| CN109384922B (en) * | 2017-08-11 | 2023-07-14 | 东进世美肯株式会社 | Polyimide precursor composition and method for producing polyimide film using same |
| CN109384921B (en) * | 2017-08-11 | 2023-07-18 | 东进世美肯株式会社 | Polyimide precursor composition and method for producing polyimide film using same |
| CN112585228A (en) * | 2018-08-22 | 2021-03-30 | Pi尖端素材株式会社 | Polyimide varnish for coating conductor containing aromatic carboxylic acid and method for producing same |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI739784B (en) | 2021-09-21 |
| TW201736511A (en) | 2017-10-16 |
| KR102531268B1 (en) | 2023-05-12 |
| CN106947080B (en) | 2024-02-23 |
| KR20170079921A (en) | 2017-07-10 |
| JP2017119869A (en) | 2017-07-06 |
| JP6928447B2 (en) | 2021-09-01 |
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