WO2014104557A1 - 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 - Google Patents
낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 Download PDFInfo
- Publication number
- WO2014104557A1 WO2014104557A1 PCT/KR2013/009763 KR2013009763W WO2014104557A1 WO 2014104557 A1 WO2014104557 A1 WO 2014104557A1 KR 2013009763 W KR2013009763 W KR 2013009763W WO 2014104557 A1 WO2014104557 A1 WO 2014104557A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- carbon atoms
- group
- aminophenoxy
- formula
- Prior art date
Links
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 83
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 72
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims abstract description 41
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 150
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical group 0.000 claims description 78
- -1 alkali metal salt Chemical class 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 150000004985 diamines Chemical class 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 238000007112 amidation reaction Methods 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 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 claims description 7
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- PCIVIPVWWQZHPX-UHFFFAOYSA-N 4-(4-aminophenyl)-3,5-bis(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=C(C(F)(F)F)C=C(N)C=C1C(F)(F)F PCIVIPVWWQZHPX-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- YKNMIGJJXKBHJE-UHFFFAOYSA-N (3-aminophenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(N)=C1 YKNMIGJJXKBHJE-UHFFFAOYSA-N 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- CGSKOGYKWHUSLC-UHFFFAOYSA-N 1-(4-aminophenyl)-1,3,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC=C(N)C=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 CGSKOGYKWHUSLC-UHFFFAOYSA-N 0.000 claims description 4
- UXOXUHMFQZEAFR-UHFFFAOYSA-N 2,2',5,5'-Tetrachlorobenzidine Chemical group C1=C(Cl)C(N)=CC(Cl)=C1C1=CC(Cl)=C(N)C=C1Cl UXOXUHMFQZEAFR-UHFFFAOYSA-N 0.000 claims description 4
- HOLGXWDGCVTMTB-UHFFFAOYSA-N 2-(2-aminophenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1N HOLGXWDGCVTMTB-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 claims description 4
- QHWXZLXQXAZQTO-UHFFFAOYSA-N 3-(3-aminophenyl)sulfinylaniline Chemical compound NC1=CC=CC(S(=O)C=2C=C(N)C=CC=2)=C1 QHWXZLXQXAZQTO-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 4
- GDGWSSXWLLHGGV-UHFFFAOYSA-N 3-(4-aminophenyl)-1,1,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC(N)=CC=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 GDGWSSXWLLHGGV-UHFFFAOYSA-N 0.000 claims description 4
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 claims description 4
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 claims description 4
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 claims description 4
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 claims description 4
- MFTFTIALAXXIMU-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MFTFTIALAXXIMU-UHFFFAOYSA-N 0.000 claims description 4
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 claims description 4
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 claims description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 4
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 4
- URMNVIKGFSSFRC-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1SC1=CC=C(N)C(N)=C1 URMNVIKGFSSFRC-UHFFFAOYSA-N 0.000 claims description 4
- NMGGOPFXZOFVKJ-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfinylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)C1=CC=C(N)C(N)=C1 NMGGOPFXZOFVKJ-UHFFFAOYSA-N 0.000 claims description 4
- JKETWUADWJKEKN-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 JKETWUADWJKEKN-UHFFFAOYSA-N 0.000 claims description 4
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 claims description 4
- MITHMOYLTXMLRB-UHFFFAOYSA-N 4-(4-aminophenyl)sulfinylaniline Chemical compound C1=CC(N)=CC=C1S(=O)C1=CC=C(N)C=C1 MITHMOYLTXMLRB-UHFFFAOYSA-N 0.000 claims description 4
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 claims description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 4
- HSBOCPVKJMBWTF-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)C1=CC=C(N)C=C1 HSBOCPVKJMBWTF-UHFFFAOYSA-N 0.000 claims description 4
- NHLGDELWVDRKBL-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenoxy]-3-(trifluoromethyl)aniline Chemical compound NC1=CC(=C(OC2=CC=C(C=C2)C(C(F)(F)F)C(F)(F)F)C=C1)C(F)(F)F NHLGDELWVDRKBL-UHFFFAOYSA-N 0.000 claims description 4
- CRIJFNDXIUWXDY-UHFFFAOYSA-N 4-[4-[2-[3-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=CC(C(C)(C)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 CRIJFNDXIUWXDY-UHFFFAOYSA-N 0.000 claims description 4
- DSXVBZHFXLKHJU-UHFFFAOYSA-N 4-[4-[2-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 DSXVBZHFXLKHJU-UHFFFAOYSA-N 0.000 claims description 4
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- PJWQLRKRVISYPL-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2-(trifluoromethyl)aniline Chemical group C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 PJWQLRKRVISYPL-UHFFFAOYSA-N 0.000 claims description 4
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 claims description 4
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 claims description 4
- FUKMZONXXALQHQ-UHFFFAOYSA-N 9,9-dimethylfluorene-2,7-diamine Chemical compound C1=C(N)C=C2C(C)(C)C3=CC(N)=CC=C3C2=C1 FUKMZONXXALQHQ-UHFFFAOYSA-N 0.000 claims description 4
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- WYYLAHMAYZBJOI-UHFFFAOYSA-N [3-[4-(3-aminophenoxy)benzoyl]phenyl]-[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=C(C=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WYYLAHMAYZBJOI-UHFFFAOYSA-N 0.000 claims description 4
- JAGJCSPSIXPCAK-UHFFFAOYSA-N [4-[4-(3-aminophenoxy)benzoyl]phenyl]-[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 JAGJCSPSIXPCAK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 claims description 4
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- PKXSNWGPLBAAJQ-UHFFFAOYSA-N naphthalene-1,3-diamine Chemical compound C1=CC=CC2=CC(N)=CC(N)=C21 PKXSNWGPLBAAJQ-UHFFFAOYSA-N 0.000 claims description 4
- OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 claims description 4
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 claims description 4
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- RDMFEHLCCOQUMH-UHFFFAOYSA-N 2,4'-Diphenyldiamine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1N RDMFEHLCCOQUMH-UHFFFAOYSA-N 0.000 claims description 3
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 claims description 3
- JFEXPVDGVLNUSC-UHFFFAOYSA-N 3-(3-aminophenyl)sulfanylaniline Chemical compound NC1=CC=CC(SC=2C=C(N)C=CC=2)=C1 JFEXPVDGVLNUSC-UHFFFAOYSA-N 0.000 claims description 3
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 claims description 3
- NRLUQVLHGAVXQB-UHFFFAOYSA-N 4-(4-amino-2-chloro-5-methoxyphenyl)-5-chloro-2-methoxyaniline Chemical group C1=C(N)C(OC)=CC(C=2C(=CC(N)=C(OC)C=2)Cl)=C1Cl NRLUQVLHGAVXQB-UHFFFAOYSA-N 0.000 claims description 3
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 claims description 3
- CNABHHDNHRETRU-UHFFFAOYSA-N 4-[4-[4-[4-[4-(4-aminophenoxy)phenoxy]phenyl]sulfonylphenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(OC=4C=CC(N)=CC=4)=CC=3)=CC=2)C=C1 CNABHHDNHRETRU-UHFFFAOYSA-N 0.000 claims description 3
- YCZUWQOJQGCZKG-UHFFFAOYSA-N 9h-carbazole-3,6-diamine Chemical compound C1=C(N)C=C2C3=CC(N)=CC=C3NC2=C1 YCZUWQOJQGCZKG-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- IEFWDQQGFDLKFK-UHFFFAOYSA-N 2-n,2-n-dimethyl-1,3,5-triazine-2,4,6-triamine Chemical compound CN(C)C1=NC(N)=NC(N)=N1 IEFWDQQGFDLKFK-UHFFFAOYSA-N 0.000 claims description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- YFBMJEBQWQBRQJ-UHFFFAOYSA-N 4-n-(4-aminophenyl)-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=CC=C1 YFBMJEBQWQBRQJ-UHFFFAOYSA-N 0.000 claims description 2
- QPDNZLWPWXPPIO-UHFFFAOYSA-N 4-n-[4-[4-(4-aminoanilino)phenyl]phenyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C=2C=CC(NC=3C=CC(N)=CC=3)=CC=2)C=C1 QPDNZLWPWXPPIO-UHFFFAOYSA-N 0.000 claims description 2
- BGQNOPFTJROKJE-UHFFFAOYSA-N 5,6-diamino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=C(N)C(=O)N(C)C1=O BGQNOPFTJROKJE-UHFFFAOYSA-N 0.000 claims description 2
- FTHBTDDIVWLRLP-UHFFFAOYSA-N 5,6-diaminopyrazine-2,3-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N=C1N FTHBTDDIVWLRLP-UHFFFAOYSA-N 0.000 claims description 2
- BBTNLADSUVOPPN-UHFFFAOYSA-N 5,6-diaminouracil Chemical compound NC=1NC(=O)NC(=O)C=1N BBTNLADSUVOPPN-UHFFFAOYSA-N 0.000 claims description 2
- ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 claims description 2
- XVMFICQRQHBOOT-UHFFFAOYSA-N 6-methoxy-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC(N)=NC(N)=N1 XVMFICQRQHBOOT-UHFFFAOYSA-N 0.000 claims description 2
- CPNAVTYCORRLMH-UHFFFAOYSA-N 6-phenylphenanthridine-3,8-diamine Chemical compound C=1C(N)=CC=C(C2=CC=C(N)C=C22)C=1N=C2C1=CC=CC=C1 CPNAVTYCORRLMH-UHFFFAOYSA-N 0.000 claims description 2
- ATCQNYLEZRQALQ-UHFFFAOYSA-N 6-propan-2-yloxy-1,3,5-triazine-2,4-diamine Chemical compound CC(C)OC1=NC(N)=NC(N)=N1 ATCQNYLEZRQALQ-UHFFFAOYSA-N 0.000 claims description 2
- KPIAHQAOODFLBZ-UHFFFAOYSA-N 9-methylcarbazole-3,6-diamine Chemical compound NC1=CC=C2N(C)C3=CC=C(N)C=C3C2=C1 KPIAHQAOODFLBZ-UHFFFAOYSA-N 0.000 claims description 2
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims description 2
- IYLLULUTZPKQBW-UHFFFAOYSA-N Acrinol Chemical compound CC(O)C(O)=O.C1=C(N)C=CC2=C(N)C3=CC(OCC)=CC=C3N=C21 IYLLULUTZPKQBW-UHFFFAOYSA-N 0.000 claims description 2
- WDVSHHCDHLJJJR-UHFFFAOYSA-N Proflavine Chemical compound C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WDVSHHCDHLJJJR-UHFFFAOYSA-N 0.000 claims description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims description 2
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004012 amifampridine Drugs 0.000 claims description 2
- UPOYFZYFGWBUKL-UHFFFAOYSA-N amiphenazole Chemical compound S1C(N)=NC(N)=C1C1=CC=CC=C1 UPOYFZYFGWBUKL-UHFFFAOYSA-N 0.000 claims description 2
- ZLNBQPMKZQSZQE-UHFFFAOYSA-N bis[4-[4-[2-(4-aminophenyl)propan-2-yl]phenoxy]phenyl]methanone Chemical compound C=1C=C(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=CC(=CC=3)C(C)(C)C=3C=CC(N)=CC=3)=CC=2)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZLNBQPMKZQSZQE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 claims description 2
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PVCOXMQIAVGPJN-UHFFFAOYSA-N piperazine-1,4-diamine Chemical compound NN1CCN(N)CC1 PVCOXMQIAVGPJN-UHFFFAOYSA-N 0.000 claims description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 claims description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002345 steroid group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- VMXLZAVIEYWCLQ-UHFFFAOYSA-N 4-(4-aminophenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1 VMXLZAVIEYWCLQ-UHFFFAOYSA-N 0.000 claims 1
- SSDBTLHMCVFQMS-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1 SSDBTLHMCVFQMS-UHFFFAOYSA-N 0.000 claims 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims 1
- VYQYKCAZJQOVJO-UHFFFAOYSA-N 9-ethylcarbazole-3,6-diamine Chemical compound NC1=CC=C2N(CC)C3=CC=C(N)C=C3C2=C1 VYQYKCAZJQOVJO-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000005375 organosiloxane group Chemical group 0.000 claims 1
- 230000029305 taxis Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 29
- 239000000758 substrate Substances 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 7
- 230000009477 glass transition Effects 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 43
- 239000000243 solution Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000010408 film Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229940113088 dimethylacetamide Drugs 0.000 description 15
- 229920001721 polyimide Polymers 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000004642 Polyimide Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 238000002411 thermogravimetry Methods 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- 0 CC(*)(*)NC(c(cc1C(N2I)=O)ccc1C2=O)=O Chemical compound CC(*)(*)NC(c(cc1C(N2I)=O)ccc1C2=O)=O 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 239000001110 calcium chloride Substances 0.000 description 7
- 229910001628 calcium chloride Inorganic materials 0.000 description 7
- 238000001879 gelation Methods 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QTQZFSLNINYVFF-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-bis(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Br)C(C(F)(F)F)=C1 QTQZFSLNINYVFF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 238000006358 imidation reaction Methods 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- QBYGJJSFMOVYOA-UHFFFAOYSA-N (4-boronophenyl)azanium;chloride Chemical compound Cl.NC1=CC=C(B(O)O)C=C1 QBYGJJSFMOVYOA-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- ARRQNZZBVOIEQQ-UHFFFAOYSA-N 1,3-dioxoisoindole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)NC(=O)C2=C1 ARRQNZZBVOIEQQ-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- ZRODGUDVLROVAI-UHFFFAOYSA-N 2-[4-[4-(5-carboxy-1,3-dioxoisoindol-2-yl)-2,6-bis(trifluoromethyl)phenyl]phenyl]-1,3-dioxoisoindole-5-carboxylic acid Chemical compound O=C1C2=CC=C(C(O)=O)C=C2C(=O)N1C(C=C1C(F)(F)F)=CC(C(F)(F)F)=C1C(C=C1)=CC=C1N1C(=O)C2=CC=C(C(=O)O)C=C2C1=O ZRODGUDVLROVAI-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- NKSQIEJTEVJKKB-UHFFFAOYSA-N 9-phenylcarbazole-3,6-diamine Chemical compound C12=CC=C(N)C=C2C2=CC(N)=CC=C2N1C1=CC=CC=C1 NKSQIEJTEVJKKB-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002305 electric material Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000000382 optic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
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
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Definitions
- the present invention relates to a soluble aromatic polyamideimide comprising a diamine monomer having an asymmetric structure having two substituents in an aromatic ring, and a method for preparing the same. More specifically, the present invention relates to a high transparency, low coefficient of thermal expansion, high glass transition temperature and high thermal properties.
- a soluble aromatic polyamideimide exhibiting stability and good solubility in organic solvents and a process for preparing the same.
- Glass substrates used in conventional flat panel displays have the advantages of high heat resistance, transparency, and barrier properties, but they can be broken when dropped, inflexible, and have a heavier weight compared to thinner thicknesses.
- Various studies are being conducted on flexible displays.
- the polyimide (PI) is a polymer having a relatively low crystallinity or a mostly amorphous structure, which is easy to synthesize, can make a thin film, and does not require a crosslinking group for curing, as well as transparency and rigid chain structure. It is a polymer material with excellent heat resistance, chemical resistance, excellent mechanical properties, electrical properties and dimensional stability. It is widely used in electric and electronic materials such as automotive, aerospace, flexible circuit board, liquid crystal alignment film for LCD, adhesive and coating agent. It is used.
- Japanese Patent Application Laid-Open No. 2010-106225 (2010.05.13.)
- a conventional technique for improving the properties of the polyamideimide includes a trifluoromethyl group, and relates to a polyimide having an amide group and a method for producing the same.
- Japanese Patent Laid-Open No. 2012-77144 (2012.04.19.) Describes a polyamideimide containing trifluoromethyl group, a method for producing the same, and a technique of using the same as a flexible substrate material.
- the first object of the present invention is to provide a novel dicarboxylic acid derivative which can be used as a monomer of polyamideimide applicable to a plastic substrate material of a flexible display, and a method for producing the same.
- the present invention provides a diamine compound using a novel diamine compound, characterized in that the two functional groups R and R 'are asymmetrically introduced into only one of the rings constituting the diamine compound.
- the present invention is an asymmetric dicarboxyl, characterized in that the two substituents R and R ', represented by the formula [A] is bonded to only one ring group A of the ring group A and ring group B Acid derivatives, alkali metal salts thereof or alkaline earth metal salts thereof; And it provides a preparation method thereof.
- R, R ', X 1 to X 3 are the same as or different from each other, and each independently, an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with one or more halogen; An alkoxy group having 1 to 12 carbon atoms which is unsubstituted or substituted with one or more halogens; Alkenyl groups having 2 to 12 carbon atoms which are unsubstituted or substituted with one or more halogens; An alkynyl group having 2 to 12 carbon atoms which is unsubstituted or substituted with one or more halogens; A cycloalkyl group having 4 to 30 carbon atoms which is unsubstituted or substituted with one or more halogens; A cycloalkenyl group having 4 to 30 carbon atoms which is unsubstituted or substituted with at least one halogen; An aryl group having 6 to 30 carbon atoms which is unsubstituted or
- R 1, R 2 and R 3 are the same or different and each is hydrogen, alkyl of 1 to 12 carbon atoms, unsubstituted or substituted with one or more halogen; Cycloalkyl having 4 to 20 carbon atoms which is unsubstituted or substituted with one or more halogens; Aryl having 6 to 20 carbon atoms which is unsubstituted or substituted with one or more halogens; Or unsubstituted or substituted with one or more halogen, heteroaryl having 3 to 20 carbon atoms;
- the ring group And are independently of each other an arylene or cycloalkylene group having 5 to 30 carbon atoms containing at least one 5- or 6-membered ring unsubstituted or substituted with one or more halogens, 5- or 6 unsubstituted or substituted with one or more halogens Or a heteroarylene or heterocycloalkylene group having 5 to 30 carbon atoms containing at least one ring.
- the present invention also provides a polyamideimide obtained by polymerizing the dicarboxylic acid derivative of the general formula (A) with a known diamine and a method for producing the same.
- the present invention provides a novel diamine represented by the formula [D] and a method for preparing the dicarboxylic acid derivative of Formula (A).
- R, R 'and a cyclic group in the formula And are the same as defined above, respectively.
- the polyamideimide obtained by the present invention introduced a bulky trifluoromethyl group irregularly in the polymer main chain to induce high solubility and transparency without deterioration of heat resistance, and the hydrogen bond between the amide bond and the polymer chain
- the polymer obtained with strong rigidity may have a high glass transition temperature.
- the polyamideimide may have a low coefficient of thermal expansion by minimizing the structural deformation of the polymer backbone due to heat, and in addition, the fluorine atoms of the polymer backbone have low water absorption, dielectric constant and refractive index due to low polarizability. And the like.
- the polyamideimide of the present invention when the polyamideimide of the present invention is formed into a film, thermal, mechanical, and optical properties can be maintained, and thus, there is an advantage that it can be applied as a substrate material of a flexible display.
- FIG. 6 is a carbon atom nuclear magnetic resonance spectroscopy spectrum of a synthesis example of a diamine compound according to another embodiment of the present invention.
- FIG. 10 is a hydrogen atom nuclear magnetic resonance spectroscopy spectrum of the polyamideimide (suBTFB-PAI2) synthesized according to an embodiment of the present invention.
- FIG. 11 is a hydrogen atom nuclear magnetic resonance spectroscopy spectrum of the polyamideimide (usBTFB-PAI) synthesized according to an embodiment of the present invention.
- DAN-PAI polyamideimide
- ODA-PAI polyamideimide
- FIG. 16 is a diagram showing the results of thermogravimetric analysis (TGA) of polyamideimide (uuBTFB-PAI) synthesized in Example 1 of the present invention.
- TGA thermal weight analysis
- FIG. 18 is a diagram showing the results of thermogravimetric analysis (TGA) of polyamideimide (suBTFB-PAI2) synthesized in Example 3 of the present invention.
- TGA thermogravimetric analysis
- the present invention provides an asymmetric dicarboxylic acid derivative represented by the following Chemical Formula A, wherein two substituents R and R 'are bonded to only one ring group A of ring group A and ring group B, and alkali thereof Provided are metal salts or alkaline earth metal salts thereof.
- R, R ', X 1 to X 3 are the same as or different from each other, and each independently, an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with one or more halogen; An alkoxy group having 1 to 12 carbon atoms which is unsubstituted or substituted with one or more halogens; Alkenyl groups having 2 to 12 carbon atoms which are unsubstituted or substituted with one or more halogens; An alkynyl group having 2 to 12 carbon atoms which is unsubstituted or substituted with one or more halogens; A cycloalkyl group having 4 to 30 carbon atoms which is unsubstituted or substituted with one or more halogens; A cycloalkenyl group having 4 to 30 carbon atoms which is unsubstituted or substituted with at least one halogen; An aryl group having 6 to 30 carbon atoms which is unsubstituted or
- R 1, R 2 and R 3 are the same or different and each is hydrogen, alkyl of 1 to 12 carbon atoms, unsubstituted or substituted with one or more halogen; Cycloalkyl having 4 to 20 carbon atoms which is unsubstituted or substituted with one or more halogens; Aryl having 6 to 20 carbon atoms which is unsubstituted or substituted with one or more halogens; Or unsubstituted or substituted with one or more halogen, heteroaryl having 3 to 20 carbon atoms;
- the ring group And are independently of each other an arylene or cycloalkylene group having 5 to 30 carbon atoms containing at least one 5- or 6-membered ring unsubstituted or substituted with one or more halogens, 5- or 6 unsubstituted or substituted with one or more halogens Or a heteroarylene or heterocycloalkylene group having 5 to 30 carbon atoms containing at least one ring.
- the two substituents R and R ' are asymmetrically introduced into two rings of the diamine to suppress various interactions of the polyimide or polyamide, and the two substituents are bulky. Characterized in that it is a group (bulky group).
- the bulky group may be an electron withdrawing group, and the electron attracting group may be a linear or branched perfluorinated alkyl group. More specifically, the linear or branched perfluorinated alkyl group may be a trifluoromethyl group.
- Examples of (iii) unsubstituted or substituted alkenyl groups having 2 to 12 carbon atoms which may be selected from the above substituents R, R ', X 1 to X 3 include ethenyl, propenyl and butenyl Or any other linear or branched carbohydrate 2 to 12 alkenyl group, and when substituted with halogen, is preferably substituted with fluorine. In this case, fluorethenyl may be mentioned.
- Examples of the (iv) unsubstituted or substituted carbolic 2-12 alkynyl group which may also be selected from the substituents R, R ', X 1 to X 3 are ethynyl, propynyl, buty It is preferable to include all of the alkynyl groups having 2 to 12 carbon atoms, which are nil or other linear or branched carbohydrates, and to be substituted with halogen, and in this case, fluorethynyl may be mentioned.
- (v) unsubstituted or substituted C4-C30 cycloalkyl groups which may be selected from the substituents R, R ', X 1 to X 3 are cyclobutyl, cyclopentyl, cyclohexyl Or other linear or branched carbohydrate 4 to 30 cycloalkyl groups, and when substituted with halogen, is preferably substituted with fluorine. In this case, fluorinated cyclobutyl may be mentioned.
- Examples of the (vi) unsubstituted or substituted with one or more halogen cycloalkenyl groups having 4 to 30 carbon atoms which may also be selected from the substituents R, R ', and X 1 to X 3 include cyclopropenyl and cyclobutenyl , Cyclopentenyl, cyclohexenyl and the like, or any other linear or branched cycloalkenyl group, and when substituted with halogen, is preferably substituted with fluorine, in which case fluorinated cyclobutenyl may be mentioned. have.
- (Viii) unsubstituted or at least one halogen, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and a halogen having 1 to 12 carbon atoms, which may be selected from the substituents R, R ', X 1 to X 3
- a heteroaryl group having 3 to 30 carbon atoms substituted with an alkyl group and / or a halogenated alkoxy group having 1 to 12 carbon atoms include pyridyl, thiophenyl, indoryl, etc. or other linear or branched alkyl groups or halogens. It includes all heteroaryl groups.
- Examples of the arylalkyl group having 6 to 30 carbon atoms substituted with an alkyl group and / or a halogenated alkoxy group having 1 to 12 carbon atoms include all of tolyl, mesitylyl, xylyl or other linear or branched alkyl groups or arylalkyl groups substituted with halogen. Include.
- Preferred substituents of R and R 'in the present invention are alkyl substituted with fluorine, alkoxy substituted with fluorine or unsubstituted or substituted aryl group, particularly preferred are perfluoroalkyl, perfluoroalkoxy, unsubstituted or substituted Phenyl, most preferred are trifluoromethyl (-CF 3 ) and pentafluoroethyl (-C 2 F 5 ).
- R and R ' are the same or different, respectively, may be a hydrocarbon group containing fluorine.
- L 1 may be any one selected from a single bond, O, S.
- R and R ' are CF 3 or C 2 F 5, respectively.
- the dicarboxylic acid derivative of the formula (A) in the present invention is a monomer consisting of a ratio of 2: 1 in the molar ratio of the formula A-2 and A-3, in order to actually obtain a dicarboxylic acid derivative of the formula (A)
- the amount of the formula A-3 is greater than 2 times, the amount of the side reactants in which the formula A-2 and the formula A-3 are combined 1: 1 may be reduced.
- the imidation reaction is a dehydration reaction
- the reaction when water is removed during the reaction, the reaction may proceed advantageously, and a water removal apparatus may be used.
- the present invention also provides a diamine represented by [Formula D], characterized in that two substituents R and R 'are asymmetrically bonded to one ring group A.
- R, R 'and a cyclic group in the formula And are the same as defined above, respectively.
- substituents R and R 'in Formula B and Formula C are the same as or different from each other, and may be a fluorine-containing hydrocarbon group, wherein L 1 is selected from a single bond, O, S It can be either.
- the polyamide-imide in the formula (B) and (C) is L 1 is a single bond, wherein L 2 is an alkylene group of 1 to 12 carbon atoms, an arylene group of 6 to 12 carbon atoms, a halogenated alkyl group of 1 to 12 carbon atoms It may be any one selected from an arylene group having 6 to 16 carbon atoms, a heteroarylene group having 2 to 12 carbon atoms, R and R 'are each alkyl having 1 to 5 carbon atoms containing fluorine,
- L 2 is
- polyamideimide obtained in the present invention may be of the following formula B-1 or C-1.
- the present invention provides a method for producing a polyamideimide represented by the formula (B) by amidation polymerization reaction of the asymmetric dicarboxylic acid derivative of the formula (A) and the diamine monomer of the formula (B-2) made through the following scheme .
- the amidation polymerization reaction may be performed by dissolving the diamine monomer and the dicarboxylic acid monomer of the formula B-2 in an organic solvent and stirring.
- the solvent examples include sulfoxide or sulfone solvents such as dimethyl sulfoxide, diphenyl sulfone, tetra methyl sulfone, and N, N-dimethylacetate.
- Amide solvents such as hexamethyl phosphate triamide, halogenated alkyl solvents such as chloroform and methylene chloride, tetrahydrofuran, 1,4-dioxane ether solvents such as (dioxane) and p-cresolmethylether, and these solvents may be used alone, and two or more kinds thereof may be used if necessary, preferably N.
- N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAc ), N-methylpyrrolidone (NMP) and dimethyl sulfoxide (DMSO)
- DMF N-dimethylformamide
- DMAc N, N-dimethylacetamide
- NMP N-methylpyrrolidone
- DMSO dimethyl sulfoxide
- the reaction temperature in the amide reaction is more preferably from 60 to 250 °C range of 80 to 200 °C and the reaction time can be stirred for 30 minutes to 20 hours.
- the amidation reaction is also a dehydration reaction
- the reaction when water is removed during the reaction, the reaction may proceed advantageously, and a water removal apparatus may be used.
- the concentration of the solution is usually about 5-20% (weight of the reactants (g) / amount of solvent (ml)).
- the temperature of the solution is raised and stirred for some time to amidate. In this case, it is preferable to remove water generated during the reaction and to promote the amidation reaction by continuously adding a small amount of dehydrating agent so that the amidation reaction proceeds effectively.
- a dehydration ring closure agent can use a well-known thing.
- the present invention comprises the steps of: a) preparing a dicarboxylic acid derivative of the general formula (C-3) by imidization reaction of the trimellitic anhydride of the general formula (A-3) with the diamine compound of the general formula (B-2); And b) subjecting the dicarboxylic acid derivative of Formula C-3 and the diamine compound of Formula A-2 to amidation polymerization, which is made through Scheme 4 below, wherein the polyamideimide represented by Formula C comprises It provides a manufacturing method.
- R, R ', X 1 to X 3, L 1, L 2 , n and a ring group And are the same as defined above.
- the imidization reaction and the amidation reaction in Schemes 3 and 4 may be carried out under the same process conditions as those of the imidization reaction in the preparation of the dicarboxylic acid derivative and the amidation reaction in the preparation of the polyimideamide.
- the diamine represented by the formula (B-2) may be 2,2'-bistrifluoromethylbenzidine, 2,6-bistrifluoromethylbenzidine, p-phenylenediamine, m-phenylenediamine, p-aminobenzylamine, m-aminobenzylamine, 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane , 4,4'-diaminodiphenylethane, 4,4'-diaminobenzanilide, 4,4'-diaminodiphenylether, 3,4'-diaminodiphenyl ether, 3,3'-di Aminodiphenyl ether, 2,4'-diaminodiphenyl ether, 2,2'-diaminodiphen
- the diamine used to prepare the polyamideimide of the present invention is a diamine different from the diamine represented by the formula (B-2), in addition to the diamine represented by the formula (B-2), 2,2'-bistrifluoromethylbenzidine , 2,6-bistrifluoromethylbenzidine, p-phenylenediamine, m-phenylenediamine, p-aminobenzylamine, m-aminobenzylamine, 4,4'-diaminodiphenylmethane, 3,4 '-Diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminobenzanilide, 4,4'-diaminodiphenylether , 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 2,4'-diaminomethylbenz
- a film can be produced by dissolving the polyamideimide obtained in the present invention in a polar aprotic organic solvent or a phenol solvent and drying the solvent.
- the polar aprotic organic solvent used at this time is N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), dimethyl sulfoxide ( DMSO) and tetrahydrofuran (THF), and the phenol solvent may be any one selected from phenol, o-cresol, m-cresol, and p-cresol, preferably DMAc.
- the structure and physical properties of the monomers and polymers according to the examples can be measured using the following method.
- IR and NMR analysis confirmed the structure of the intermediate compound and polyamideimide material obtained from the present invention.
- the IR diagram was obtained from Bruker's FTIR EQUINOX-55 spectrophotometer using KBr or film, and the NMR diagram was obtained from chloroform, dimethylsulfoxide. Samples can be melted on the side- d 6 and measured using a Bruker Fourier Transform AVANCE 400 spectrometer.
- the intrinsic viscosity of the synthesized polymer can be measured by dissolving the sample in N-methylpyrrolidone (NMP) solvent at a concentration of 0.5 g / dL and using a Ubbelohde type viscometer at 30 ° C.
- NMP N-methylpyrrolidone
- TGA Thermogravimetric Analysis
- DSC Differential Scanning Calorimetry
- TMA Thermomechanical Analysis
- a 5% weight loss temperature can be obtained from the TGA analysis, and the film softening temperature (T s ) can be selected in the TMA plot where the slope of the curve begins to increase rapidly, and in the case of TMA analysis at 300 ° C. After three repetitions at a rate of 5 ° C./min, the last third measurement can measure the change by raising the temperature to 600 ° C.
- the coefficient of thermal expansion (CTE) can be calculated using varying lengths in the temperature range of 50-250 ° C for the second and third measurements, respectively.
- the refractive index can be used Sairon SPA-4000 prism coupler with a laser having a wavelength of 630 and 1310 nm as a light source. The measurement may be performed to prepare a uniform film having a thickness of ⁇ 6 ⁇ m, and to measure the horizontal and vertical refractive indices at room temperature, respectively.
- Tables 1 to 4 below show the physical properties of the polyimideamide obtained according to the embodiment of the present invention.
- Table 2 shows the glass transition temperature of the polyamideimide obtained according to Examples 1 to 7, the temperature at 5% weight loss, the glass expansion coefficient and the wavelength at which the light transmission begins to start, the transmittance at 550 nm. And physical properties such as film thickness.
- Table 3 shows the solubility in various solvents of the polyamideimide prepared in Examples 1-7.
- NMP N-methylpyrrolidone
- DMAc N, N-dimethylacetamide
- DMF N, N-dimethylformamide
- DMSO dimethyl sulfoxide
- THF tetrahydrofuran
- EA ethyl acetate
- the polyamideimide of the present invention is selectively dissolved in solvents such as m-cresol, THF, NMP, DMAc, DMF, and DMSO depending on the type of diamine monomer. Can be.
- a is a refractive index in the horizontal direction
- b is a refractive index in the vertical direction
- c is an average refractive index
- d is a birefringence index
- e is a dielectric constant calculated by the average refractive index ( ⁇ >> 1.10 n av 2 )
- f is The film thickness is shown.
- the present invention is applicable to a plastic substrate of a flexible display by providing a new polyamideimide comprising an amide bond and an imide bond in a polymer backbone.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Indole Compounds (AREA)
- Polyamides (AREA)
Abstract
Description
Claims (27)
- 하기 [화학식 A]로 표시되는,두 개의 치환기 R 및 R'가 고리그룹A와 고리그룹B 중 한쪽의 고리그룹A에만 결합되어 있는 것을 특징으로 하는 비대칭 디카르복실산 유도체, 이의 알카리금속 염 또는 이의 알카리토금속 염.[화학식 A]상기 화학식 A에서R, R', X1 내지 X3 은 각각 동일하거나 상이하며 서로 독립적으로, 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 1 내지 12의 알킬기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 1 내지 12의 알콕시기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 2 내지 12의 알케닐기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 2 내지 12의 알키닐기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 4 내지 30의 시클로알킬기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 4 내지 30의 시클로알케닐기; 치환되지 않거나 하나 이상의 할로겐, 탄소수 1 내지 12의 알킬기, 탄소수 1 내지 12의 알콕시기, 탄소수 1 내지 12의 할로겐화 알킬기 및/또는 탄소수 1 내지 12의 할로겐화 알콕시기로 치환된 탄소수 6 내지 30의 아릴기; 치환되지 않거나 하나 이상의 할로겐, 탄소수 1 내지 12의 알킬기, 탄소수 1 내지 12의 알콕시기, 탄소수 1 내지 12의 할로겐화 알킬기 및/또는 탄소수 1 내지 12의 할로겐화 알콕시기로 치환된 탄소수 3 내지 30의 헤테로아릴기; 치환되지 않거나 하나 이상의 할로겐, 탄소수 1 내지 12의 알킬기, 탄소수 1 내지 12의 알콕시기, 탄소수 1 내지 12의 할로겐화 알킬기 및/또는 탄소수 1 내지 12의 할로겐화 알콕시기로 치환된 탄소수 6 내지 30의 아릴알킬기;에서 선택되는 관능기이고,L1은 단일결합, -O-, -S-, -C(=O)O-, -OC(=O)-, -C(=O)-, -SO2-, -C(R1)(R2)-, -NR3 에서 선택되는 어느 하나로서,여기서 R1, R2 및 R3 는 각각 동일하거나 상이하며, 수소, 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 1 내지 12의 알킬; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 4 내지 20의 시클로알킬; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 6 내지 20의 아릴; 또는 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 3 내지 20의 헤테로아릴;에서 선택되는 어느 하나이며,
- 제 1 항에 있어서,상기 R과 R'는 각각 동일하거나 상이하며, 불소를 함유하는 탄화수소기인 것을 특징으로 하는 디카르복실산 유도체, 이의 알카리금속 염 또는 이의 알카리토금속 염.
- 제 1 항에 있어서,상기 L1은 단일결합, O, S 중에서 선택되는 어느 하나인 것을 특징으로 하는 디카르복실산 유도체, 이의 알카리금속 염 또는 이의 알카리토금속 염.
- 제 6 항에 있어서,상기 반응식 1의 이미드화 반응은 빙초산에서 탈수화 반응으로 이루어지는 것을 특징으로 하는 디카르복실산 유도체의 제조방법
- 하기 [화학식 B] 또는 [화학식C]로 표시되는 폴리아미드이미드.[화학식 B][화학식 C]상기 [화학식 B] 및 [화학식 C]에서,L2는 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 1 내지 20의 알킬렌기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 6 내지 20의 아릴렌기; 탄소수 1 내지 12의 알킬기, 탄소수 1내지 12의 알콕시기, 탄소수 1내지 12의 할로겐화 알킬기 또는 탄소수 1내지 12의 할로겐화 알콕시기로 치환된 탄소수 6내지 30의 아릴렌기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 2 내지 20의 헤테로아릴렌기; 치환되지 않거나 하나 이상의 할로겐으로 치환된 탄소수 4 내지 20의 시클로알킬렌기; 중에서 선택되는 어느 하나이며,상기 n은 10 내지 5,000,000에서 선택되는 정수이다.
- 제 8 항에 있어서,상기 R 과 R'는 각각 동일하거나 상이하며, 불소를 함유하는 탄화수소기인 것을 특징으로 하는 폴리아미드이미드.
- 제 8 항에 있어서,상기 L1은 단일결합, O, S 중에서 선택되는 어느 하나인 것을 특징으로 하는 폴리아미드이미드.
- 제 10 항에 있어서,상기 L1은 단일결합이고,상기 L2는 탄소수 1내지 12의 알킬렌기, 탄소수 6내지 12의 아릴렌기, 탄소수 1내지 12의 할로겐화 알킬기로 치환된 탄소수 6 내지 16의 아릴렌기, 탄소수 2 내지 12의 헤테로아릴렌기에서 선택되는 어느 하나이며,상기 R과 R'는 각각 불소를 포함하는 탄소수 1 내지 5의 알킬이고,상기 X1 내지 X3은 각각 동일하거나 상이하며, 수소, 할로겐, 트리플루오로메틸기, 탄소수 1 내지 5의 알킬기, 탄소수 1 내지 5의 알콕시기로 이루어진 군으로 선택되며,
- 하기 반응식 3을 통해 이루어지는, a) 화학식 A-3의 트라이멜리틱 무수물과 화학식 B-2의 디아민 화합물을 이미드화 반응함으로써 화학식 C-3의 디카르복실산 유도체를 제조하는 단계; 및 b) 하기 반응식 4를 통해 이루어지는, 상기 화학식 C-3의 디카르복실산 유도체와 화학식 A-2의 디아민 화합물을 아미드화 중합반응을 시키는 단계;를 포함하는 화학식 C로 표시되는 폴리아미드이미드의 제조방법[반응식 3][반응식 4]상기 반응식 3 및 반응식 4 에서
- 제 14 항 내지 제 15 항 중 어느 한 항에 있어서,상기 화학식 B-2로 표시되는 디아민은 2,2'-비스트리플루오로메틸벤지딘, 2,6-비스트리플루오로메틸벤지딘, p-페닐렌디아민, m-페닐렌디아민, p-아미노벤질아민, m-아미노벤질아민, 4,4'-다이아미노다이페닐메탄, 3,4'-다이아미노다이페닐메탄, 3,3'-다이아미노다이페닐메탄, 4,4'-디아미노디페닐에탄, 4,4'-디아미노벤즈아닐리드, 4,4'-디아미노디페닐에테르, 3,4'-다이아미노다이페닐 에테르, 3,3'-다이아미노다이페닐 에테르, 2,4'-다이아미노다이페닐 에테르, 2,2'-다이아미노다이페닐 에테르, 2,3'-다이아미노다이페닐 에테르, 1,4-비스(4-아미노페녹시)벤젠, 1,4-비스(3-아미노페녹시)벤젠, 1,3-비스(4-아미노페녹시)벤젠, 1,3-비스(3-아미노페녹시)벤젠, 2,2-비스[4-(4-아미노페녹시)페닐]프로판, 2,2-비스[4-(3-아미노페녹시)페닐]프로판, 비스(4-아미노페닐)설파이드, 비스(3-아미노페닐)설파이드, 3,4-다이아미노페닐설파이드, 비스(4-아미노페닐)술폭사이드, 비스(3-아미노페닐)술폭사이드, 3,4-다이아미노페닐술폭사이드, 비스(4-아미노페닐)술폰, 비스(3-아미노페닐)술폰, 3,4-다이아미노페닐술폰, 4,4'-다이아미노벤조페논, 3,4'-다이아미노벤조페논, 3,3'-다이아미노벤조페논, 비스[4-(4-아미노페녹시)페닐]술폰, 비스[4-(3-아미노페녹시)페닐]술폰, 비스[4-(4-아미노페녹시)페닐]에테르, 1,4-비스[4-(3-아미노페녹시)벤조일]벤젠, 1,3-비스[4-(3-아미노페녹시)벤조일]벤젠, 4,4'-비스[3-(4-아미노페녹시)벤조일]다이페닐에테르, 4,4'-비스[3-(3-아미노페녹시)벤조일]다이페닐에테르, 4,4'-비스[4-(4-아미노-알파,알파-다이메틸벤질)페녹시]벤조페논, 4,4'-비스[4-(4-아미노-알파,알파-다이메틸벤질)페녹시]다이페닐술폰, 비스[4-{4-(4-아미노페녹시)페녹시}페닐]술폰, 1,4-비스[4-(4-아미노페녹시)-알파,알파-다이메틸벤질]벤젠, 1,3-비스[4-(4-아미노페녹시)-알파,알파-다이메틸벤질]벤젠, 2,2-비스[4-(4-아미노페녹시)페닐]-1,1,1,3,3,3-헥사플루오로프로판, 2,2-비스[4-(3-아미노페녹시)페닐]-1,1,1,3,3,3-헥사플루오로프로판, 1,3-디아미노나프탈렌, 1,4-디아미노나프탈렌, 1,5-디아미노나프탈렌, 2,6-디아미노나프탈렌, 2,2'-디메틸-4,4'-디아미노비페닐, 3,3'-디메틸-4,4'-디아미노비페닐, 2,2'-디트리플루오로메틸-4,4'-디아미노비페닐, 3,3'-디트리플루오로메틸-4,4'-디아미노비페닐, 5-아미노-1-(4'-아미노페닐)-1,3,3-트리메틸인단, 6-아미노-1-(4'-아미노페닐)-1,3,3-트리메틸인단, 2,2-비스[4-(4-아미노페녹시)페닐]프로판, 2,2-비스[4-(4-아미노페녹시)페닐]헥사플루오로프로판, 2,2-비스(4-아미노페닐)헥사플루오로프로판, 2,2-비스[4-(4-아미노페녹시)페닐]술폰, 1,4-비스(4-아미노페녹시)벤젠, 1,3-비스(4-아미노페녹시)벤젠, 1,3-비스(3-아미노페녹시)벤젠, 9,9-비스(4-아미노페닐)-10-히드로안트라센, 2,7-디아미노플루오렌, 9,9-디메틸-2,7-디아미노플루오렌, 9,9-비스(4-아미노페닐)플루오렌, 4,4'-메틸렌-비스(2-클로로아닐린), 2,2',5,5'-테트라클로로-4,4'-디아미노비페닐, 2,2'-디클로로-4,4'-디아미노-5,5'-디메톡시비페닐, 3,3'-디메톡시-4,4'-디아미노비페닐, 1,4,4'-(p-페닐렌이소프로필리덴)비스아닐린, 4,4'-(m-페닐렌이소프로필리덴)비스아닐린, 2,2'-비스[4-(4-아미노-2-트리플루오로메틸페녹시)페닐]헥사플루오로프로판, 4,4'-디아미노-2,2'-비스(트리플루오로메틸)비페닐, 4,4'-비스[(4-아미노-2-트리플루오로메틸)페녹시]-옥타플루오로비페닐 중에서 선택되어지는 어느 하나인 것을 특징으로 하는 폴리아미드이미드의 제조방법
- 제 16 항에 있어서,상기 폴리아미드이미드를 제조하기 위해 사용되는 디아민은 화학식 B-2로 표시되는 디아민에 추가적으로, 상기 화학식 B-2의 디아민과 상이한 디아민으로서, 2,2'-비스트리플루오로메틸벤지딘, 2,6-비스트리플루오로메틸벤지딘, p-페닐렌디아민, m-페닐렌디아민, p-아미노벤질아민, m-아미노벤질아민, 4,4'-다이아미노다이페닐메탄, 3,4'-다이아미노다이페닐메탄, 3,3'-다이아미노다이페닐메탄, 4,4'-디아미노디페닐에탄, 4,4'-디아미노벤즈아닐리드, 4,4'-디아미노디페닐에테르, 3,4'-다이아미노다이페닐 에테르, 3,3'-다이아미노다이페닐 에테르, 2,4'-다이아미노다이페닐 에테르, 2,2'-다이아미노다이페닐 에테르, 2,3'-다이아미노다이페닐 에테르, 1,4-비스(4-아미노페녹시)벤젠, 1,4-비스(3-아미노페녹시)벤젠, 1,3-비스(4-아미노페녹시)벤젠, 1,3-비스(3-아미노페녹시)벤젠, 2,2-비스[4-(4-아미노페녹시)페닐]프로판, 2,2-비스[4-(3-아미노페녹시)페닐]프로판, 비스(4-아미노페닐)설파이드, 비스(3-아미노페닐)설파이드, 3,4-다이아미노페닐설파이드, 비스(4-아미노페닐)술폭사이드, 비스(3-아미노페닐)술폭사이드, 3,4-다이아미노페닐술폭사이드, 비스(4-아미노페닐)술폰, 비스(3-아미노페닐)술폰, 3,4-다이아미노페닐술폰, 4,4'-다이아미노벤조페논, 3,4'-다이아미노벤조페논, 3,3'-다이아미노벤조페논, 비스[4-(4-아미노페녹시)페닐]술폰, 비스[4-(3-아미노페녹시)페닐]술폰, 비스[4-(4-아미노페녹시)페닐]에테르, 1,4-비스[4-(3-아미노페녹시)벤조일]벤젠, 1,3-비스[4-(3-아미노페녹시)벤조일]벤젠, 4,4'-비스[3-(4-아미노페녹시)벤조일]다이페닐에테르, 4,4'-비스[3-(3-아미노페녹시)벤조일]다이페닐에테르, 4,4'-비스[4-(4-아미노-알파,알파-다이메틸벤질)페녹시]벤조페논, 4,4'-비스[4-(4-아미노-알파,알파-다이메틸벤질)페녹시]다이페닐술폰, 비스[4-{4-(4-아미노페녹시)페녹시}페닐]술폰, 1,4-비스[4-(4-아미노페녹시)-알파,알파-다이메틸벤질]벤젠, 1,3-비스[4-(4-아미노페녹시)-알파,알파-다이메틸벤질]벤젠, 2,2-비스[4-(4-아미노페녹시)페닐]-1,1,1,3,3,3-헥사플루오로프로판, 2,2-비스[4-(3-아미노페녹시)페닐]-1,1,1,3,3,3-헥사플루오로프로판, 1,3-디아미노나프탈렌, 1,4-디아미노나프탈렌, 1,5-디아미노나프탈렌, 2,6-디아미노나프탈렌, 2,2'-디메틸-4,4'-디아미노비페닐, 3,3'-디메틸-4,4'-디아미노비페닐, 2,2'-디트리플루오로메틸-4,4'-디아미노비페닐, 3,3'-디트리플루오로메틸-4,4'-디아미노비페닐, 5-아미노-1-(4'-아미노페닐)-1,3,3-트리메틸인단, 6-아미노-1-(4'-아미노페닐)-1,3,3-트리메틸인단, 2,2-비스[4-(4-아미노페녹시)페닐]프로판, 2,2-비스[4-(4-아미노페녹시)페닐]헥사플루오로프로판, 2,2-비스(4-아미노페닐)헥사플루오로프로판, 2,2-비스[4-(4-아미노페녹시)페닐]술폰, 1,4-비스(4-아미노페녹시)벤젠, 1,3-비스(4-아미노페녹시)벤젠, 1,3-비스(3-아미노페녹시)벤젠, 9,9-비스(4-아미노페닐)-10-히드로안트라센, 2,7-디아미노플루오렌, 9,9-디메틸-2,7-디아미노플루오렌, 9,9-비스(4-아미노페닐)플루오렌, 4,4'-메틸렌-비스(2-클로로아닐린), 2,2',5,5'-테트라클로로-4,4'-디아미노비페닐, 2,2'-디클로로-4,4'-디아미노-5,5'-디메톡시비페닐, 3,3'-디메톡시-4,4'-디아미노비페닐, 1,4,4'-(p-페닐렌이소프로필리덴)비스아닐린, 4,4'-(m-페닐렌이소프로필리덴)비스아닐린, 2,2'-비스[4-(4-아미노-2-트리플루오로메틸페녹시)페닐]헥사플루오로프로판, 4,4'-디아미노-2,2'-비스(트리플루오로메틸)비페닐, 4,4'-비스[(4-아미노-2-트리플루오로메틸)페녹시]-옥타플루오로비페닐, 1,1-메타크실릴렌디아민, 1,3-프로판디아민, 테트라메틸렌디아민, 펜타메틸렌디아민, 헥사메틸렌디아민, 헵타메틸렌디아민, 옥타메틸렌디아민, 노나메틸렌디아민, 1,4-디아미노시클로헥산, 이소포론디아민, 테트라히드로디시클로펜타디에닐렌디아민, 헥사히드로-4,7-메타노인다닐렌디메틸렌디아민, 트리시클로[6.2.1.02,7]-운데실렌디메틸디아민, 4,4'-메틸렌비스(시클로헥실아민) 및 2,3-디아미노피리딘, 2,6-디아미노피리딘, 3,4-디아미노피리딘, 2,4-디아미노피리미딘, 5,6-디아미노-2,3-디시아노피라진, 5,6-디아미노-2,4-디히드록시피리미딘, 2,4-디아미노-6-디메틸아미노-1,3,5-트리아진, 1,4-비스(3-아미노프로필)피페라진, 2,4-디아미노-6-이소프로폭시-1,3,5-트리아진, 2,4-디아미노-6-메톡시-1,3,5-트리아진, 2,4-디아미노-6-페닐-1,3,5-트리아진, 2,4-디아미노-6-메틸-s-트리아진, 2,4-디아미노-1,3,5-트리아진, 4,6-디아미노-2-비닐-s-트리아진, 2,4-디아미노-5-페닐티아졸, 2,6-디아미노푸린, 5,6-디아미노-1,3-디메틸우라실, 3,5-디아미노-1,2,4-트리아졸, 6,9-디아미노-2-에톡시아크리딘락테이트, 3,8-디아미노-6-페닐페난트리딘, 1,4-디아미노피페라진, 3,6-디아미노아크리딘, 비스(4-아미노페닐)페닐아민, 3,6-디아미노카르바졸, N-메틸-3,6-디아미노카르바졸, N-에틸-3,6-디아미노카르바졸, N-페닐-3,6-디아미노카르바졸, N,N'-디(4-아미노페닐)-벤지딘 등의 분자 내에 2개의 1급 아미노기 및 상기 1급 아미노기 이외의 질소 원자를 갖는 디아민, 디아미노오르가노실록산, 스테로이드기를 포함하는 디아민, 아세틸렌기를 포함하는 강직성의 디아민으로 이루어지는 군으로부터 선택된 어느 하나가 혼합되어 사용되는 것을 특징으로 하는 폴리아미드이미드의 제조방법
- 제 14 항 내지 제 15 항 중 어느 한 항에 있어서,상기 아미드화 중합반응은 디아민 단량체와 디카르복실산 단량체를 유기 용매에 용해시켜 80 내지 200 ℃ 에서 교반함으로써 아미드화시키는 단계를 포함하는 것을 특징으로 폴리아미드이미드의 제조방법
- 제 18 항에 있어서,상기 유기용매는 N,N-다이메틸포름아마이드(DMF), N,N-다이메틸아세트아마이드(DMAc), N-메틸피롤리돈(NMP) 및 다이메틸술폭사이드(DMSO)로 이루어지는 군으로부터 선택되는 것을 특징으로 하는 폴리아미드이미드의 제조방법
- 제8항 내지 제13항 중 어느 하나의 항에 기재된 폴리아미드이미드를 극성 비양성자성 유기용매 또는 페놀류 용매에 용해시킨 후에 상기용매를 건조함으로써 제조되는 필름
- 제 20 항에 있어서,상기 극성 비양성자성 유기용매는 N,N-다이메틸포름아마이드(DMF), N,N-다이메틸아세트아마이드(DMAc), N-메틸피롤리돈(NMP), 다이메틸술폭사이드(DMSO), 테트라하이드로퓨란(THF) 중에서 선택되는 어느 하나이고, 페놀류 용매는 페놀, o-크레졸, m-크레졸, p-크레졸 중에서 선택되는 어느 하나인 것을 특징으로 하는 필름.
- 제 22 항에 있어서,상기 R과 R'는 각각 동일하거나 상이하며, 불소를 함유하는 탄화수소기인 것을 특징으로 하는 디아민.
- a) 하기 반응식 5를 통해 이루어지고,하기 화학식 D-2의 니트로기를 포함한 화합물과 하기 화학식 D-3 의 아민 화합물 또는 화학식 D-4의 니트로기를 포함한 화합물을 스즈끼 커플링(Suzuki Coupling) 반응시켜 화학식 D-5로 표시되는 모노니트로 화합물 또는 화학식 D-6으로 표시되는 디니트로 화합물을 제조하는 단계; 및b) 하기 반응식 6을 통해 이루어지며,상기 화학식 D-5로 표시되는 모노니트로 화합물 또는 화학식 D-6으로 표시되는 디니트로 화합물의 모든 니트로기를 환원시키는 단계;를 포함하는 하기 화학식 D로 표시되는 디아민의 제조방법[반응식 5][반응식 6]
- 제 26 항에 있어서,상기 a) 단계에서 스즈키 커플링은 팔라듐 착물 촉매를 사용하여 이루어지는 것을 특징으로 하는 디아민의 제조방법
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13866653.2A EP2940015A4 (en) | 2012-12-27 | 2013-10-31 | NOVEL POLYAMIDIMIDE WITH LOW HEAT EXTRACTION COEFFICIENT |
US14/758,312 US20160194449A1 (en) | 2012-12-27 | 2013-10-31 | Novel polyamideimide having low thermal expansion coefficient |
JP2015546369A JP6087446B2 (ja) | 2012-12-27 | 2013-10-31 | 低い熱膨張係数を有する新規なポリアミドイミド |
US15/806,498 US20180066110A1 (en) | 2012-12-27 | 2017-11-08 | Novel polyamideimide having low thermal expansion coefficient |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2012-0155221 | 2012-12-27 | ||
KR1020120155221A KR101529496B1 (ko) | 2012-12-27 | 2012-12-27 | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/758,312 A-371-Of-International US20160194449A1 (en) | 2012-12-27 | 2013-10-31 | Novel polyamideimide having low thermal expansion coefficient |
US15/806,498 Division US20180066110A1 (en) | 2012-12-27 | 2017-11-08 | Novel polyamideimide having low thermal expansion coefficient |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014104557A1 true WO2014104557A1 (ko) | 2014-07-03 |
Family
ID=51021568
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2013/009763 WO2014104557A1 (ko) | 2012-12-27 | 2013-10-31 | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 |
Country Status (5)
Country | Link |
---|---|
US (2) | US20160194449A1 (ko) |
EP (1) | EP2940015A4 (ko) |
JP (3) | JP6087446B2 (ko) |
KR (1) | KR101529496B1 (ko) |
WO (1) | WO2014104557A1 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019022251A1 (ja) | 2017-07-28 | 2019-01-31 | 三菱瓦斯化学株式会社 | 新規な(ポリ)アミン化合物、樹脂、及び硬化物 |
CN112778140A (zh) * | 2020-12-29 | 2021-05-11 | 宁波博雅聚力新材料科技有限公司 | 一种含芴二胺单体、聚酰亚胺薄膜及其制备方法和用途 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101529496B1 (ko) * | 2012-12-27 | 2015-06-22 | 한국과학기술원 | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 |
KR102232009B1 (ko) | 2014-12-30 | 2021-03-25 | 코오롱인더스트리 주식회사 | 폴리아마이드-이미드 전구체, 폴리아마이드-이미드 필름 및 이를 포함하는 표시소자 |
WO2016108631A1 (ko) * | 2014-12-30 | 2016-07-07 | 코오롱인더스트리 주식회사 | 폴리아마이드-이미드 전구체, 폴리아마이드-이미드 필름 및 이를 포함하는 표시소자 |
KR102339037B1 (ko) | 2015-06-26 | 2021-12-14 | 코오롱인더스트리 주식회사 | 폴리아마이드-이미드 전구체, 폴리아마이드-이미드 필름 및 이를 포함하는 표시소자 |
CN106750443B (zh) * | 2016-12-26 | 2020-03-20 | 自贡中天胜新材料科技有限公司 | 一种热塑性聚酰亚胺预浸料及其复合材料的制备方法 |
KR101831884B1 (ko) * | 2017-02-08 | 2018-02-26 | 에스케이씨 주식회사 | 폴리아마이드-이미드 필름 |
CN111471176B (zh) * | 2020-06-02 | 2020-09-25 | 武汉柔显科技股份有限公司 | 一种聚酰亚胺前体、聚酰亚胺、薄膜及显示装置 |
CN113736084B (zh) * | 2021-09-03 | 2023-12-22 | 江苏慧智新材料科技有限公司 | 一种透明性聚酰胺酰亚胺树脂及其制备方法和应用 |
KR20240117279A (ko) | 2023-01-25 | 2024-08-01 | 한국과학기술원 | 산무수물 화합물, 이를 이용한 폴리아미드이미드 수지 및 필름 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010106225A (ja) | 2008-09-30 | 2010-05-13 | Nissan Chem Ind Ltd | 新規なフッ素化テトラカルボン酸二無水物、これより得られるポリイミド前駆体、ポリイミドとその利用 |
JP2012077144A (ja) | 2010-09-30 | 2012-04-19 | Kaneka Corp | ポリアミドイミド樹脂およびその製造方法、ポリアミドイミド樹脂溶液、ポリアミドイミド膜およびその利用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4026876A (en) * | 1975-01-20 | 1977-05-31 | Ciba-Geigy Corporation | Soluble polyamide-imides derived from phenylindane diamines |
JP2509252B2 (ja) * | 1986-11-13 | 1996-06-19 | 出光興産株式会社 | 新規共重合体とその製造法 |
US5324813A (en) * | 1992-07-22 | 1994-06-28 | International Business Machines Corporation | Low dielectric constant fluorinated polymers and methods of fabrication thereof |
KR100600449B1 (ko) * | 1999-10-25 | 2006-07-13 | 삼성토탈 주식회사 | 트리플루오로메틸기를 갖는 비대칭 구조의 다이아민 단량체 및 이를 사용하여 제조되는 가용성 방향족 폴리이미드 |
TWI330183B (ko) * | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
JP4161678B2 (ja) * | 2002-10-22 | 2008-10-08 | チッソ株式会社 | ジアミン、それを用いた配向膜、および該配向膜を有する液晶表示素子 |
MX2012001974A (es) * | 2009-08-19 | 2012-04-11 | Ambit Biosciences Corp | Compuestos de biarilo y metodos de uso de los mismos. |
KR101199744B1 (ko) * | 2012-02-28 | 2012-11-08 | (주)엘지하우시스 | 합성목재 제조용 압출다이, 이를 포함하는 제조장치 및 제조방법과 이로부터 제조된 합성목재 |
KR101385279B1 (ko) * | 2012-03-09 | 2014-04-16 | 한국과학기술원 | 두 개의 치환기를 비대칭 구조로 포함하는 디아민 화합물, 이를 사용하여 제조된 중합체 |
KR101529496B1 (ko) * | 2012-12-27 | 2015-06-22 | 한국과학기술원 | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 |
-
2012
- 2012-12-27 KR KR1020120155221A patent/KR101529496B1/ko active IP Right Grant
-
2013
- 2013-10-31 US US14/758,312 patent/US20160194449A1/en not_active Abandoned
- 2013-10-31 JP JP2015546369A patent/JP6087446B2/ja active Active
- 2013-10-31 WO PCT/KR2013/009763 patent/WO2014104557A1/ko active Application Filing
- 2013-10-31 EP EP13866653.2A patent/EP2940015A4/en not_active Withdrawn
-
2017
- 2017-02-01 JP JP2017017096A patent/JP2017125019A/ja not_active Ceased
- 2017-11-08 US US15/806,498 patent/US20180066110A1/en not_active Abandoned
-
2018
- 2018-08-13 JP JP2018152201A patent/JP2018199822A/ja active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010106225A (ja) | 2008-09-30 | 2010-05-13 | Nissan Chem Ind Ltd | 新規なフッ素化テトラカルボン酸二無水物、これより得られるポリイミド前駆体、ポリイミドとその利用 |
JP2012077144A (ja) | 2010-09-30 | 2012-04-19 | Kaneka Corp | ポリアミドイミド樹脂およびその製造方法、ポリアミドイミド樹脂溶液、ポリアミドイミド膜およびその利用 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2940015A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019022251A1 (ja) | 2017-07-28 | 2019-01-31 | 三菱瓦斯化学株式会社 | 新規な(ポリ)アミン化合物、樹脂、及び硬化物 |
KR20200032104A (ko) | 2017-07-28 | 2020-03-25 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 신규한 (폴리)아민 화합물, 수지, 및 경화물 |
CN112778140A (zh) * | 2020-12-29 | 2021-05-11 | 宁波博雅聚力新材料科技有限公司 | 一种含芴二胺单体、聚酰亚胺薄膜及其制备方法和用途 |
Also Published As
Publication number | Publication date |
---|---|
KR101529496B1 (ko) | 2015-06-22 |
JP2018199822A (ja) | 2018-12-20 |
JP2017125019A (ja) | 2017-07-20 |
EP2940015A4 (en) | 2016-09-28 |
KR20140085064A (ko) | 2014-07-07 |
EP2940015A1 (en) | 2015-11-04 |
US20180066110A1 (en) | 2018-03-08 |
JP6087446B2 (ja) | 2017-03-01 |
JP2016502560A (ja) | 2016-01-28 |
US20160194449A1 (en) | 2016-07-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2014104557A1 (ko) | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 | |
WO2013133508A1 (ko) | 두 개의 치환기를 비대칭 구조로 포함하는 디아민 화합물, 이를 사용하여 제조된 중합체 | |
WO2015183056A1 (ko) | 폴리이미드계 용액 및 이를 이용하여 제조된 폴리이미드계 필름 | |
WO2017111299A1 (ko) | 접착력이 향상된 폴리아믹산 조성물 및 이를 포함하는 폴리이미드 필름 | |
WO2017111300A1 (ko) | 신규 구조의 디아민 모노머를 적용한 폴리아믹산 용액 및 이를 포함하는 폴리이미드 필름 | |
WO2017188630A1 (ko) | 고강도 투명 폴리아미드이미드 및 이의 제조방법 | |
WO2017209414A1 (ko) | 고강도 투명 폴리아미드이미드 및 이의 제조방법 | |
WO2018038436A1 (ko) | 디아민 화합물 및 이의 제조방법 | |
EP2553001A2 (en) | Polyimide film | |
WO2020138645A1 (ko) | 폴리아믹산 조성물, 및 이를 이용한 투명 폴리이미드 필름 | |
WO2020159085A1 (ko) | 폴리아미드 수지 필름 및 이를 이용한 수지 적층체 | |
WO2017204462A1 (ko) | 폴리아미드이미드, 이의 제조방법 및 이를 이용한 폴리아미드이미드 필름 | |
WO2018117551A1 (ko) | 투명 폴리이미드 필름 | |
WO2016140559A1 (ko) | 광전소자의 플렉시블 기판용 폴리이미드 필름용 조성물 | |
WO2018080222A2 (ko) | 폴리이미드 필름 형성용 조성물 및 이를 이용하여 제조된 폴리이미드 필름 | |
WO2020159174A1 (ko) | 폴리이미드계 수지 필름 및 이를 이용한 디스플레이 장치용 기판, 및 광학 장치 | |
WO2020141713A1 (ko) | 신규한 디카르보닐 화합물을 포함하는 폴리아믹산 조성물의 제조방법, 폴리아믹산 조성물, 이를 이용한 폴리아미드-이미드 필름의 제조방법 및 그 제조방법을 통해 제조된 폴리아미드-이미드 필름. | |
WO2021060752A1 (ko) | 우수한 표면 평탄성을 갖는 폴리이미드계 필름 및 이의 제조방법 | |
WO2015182925A1 (ko) | 신규 디아민 합성 및 이를 이용한 액정 배향제 | |
WO2020159086A1 (ko) | 폴리아미드 수지 필름 및 이를 이용한 수지 적층체 | |
WO2020159035A1 (ko) | 폴리이미드 필름, 이를 이용한 플렉서블 기판 및 플렉서블 기판을 포함하는 플렉서블 디스플레이 | |
WO2020105933A1 (ko) | 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정표시소자 | |
KR101518240B1 (ko) | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 | |
WO2020130552A1 (ko) | 디아민 화합물, 이를 이용한 폴리이미드 전구체 및 폴리이미드 필름 | |
WO2020138644A1 (ko) | 폴리아믹산 조성물, 및 이를 이용한 투명 폴리이미드 필름 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13866653 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2015546369 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14758312 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013866653 Country of ref document: EP |