CN118184523B - 二胺化合物、其中间体及聚酰亚胺薄膜 - Google Patents
二胺化合物、其中间体及聚酰亚胺薄膜 Download PDFInfo
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- -1 Diamine compound Chemical class 0.000 title claims abstract description 48
- 229920001721 polyimide Polymers 0.000 title claims abstract description 40
- 239000004642 Polyimide Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229920005575 poly(amic acid) Polymers 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000009975 flexible effect Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 230000009477 glass transition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- ZKAOVABYLXQUTI-UHFFFAOYSA-N (2-acetylphenyl)boronic acid Chemical compound CC(=O)C1=CC=CC=C1B(O)O ZKAOVABYLXQUTI-UHFFFAOYSA-N 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- IQTHEAQKKVAXGV-UHFFFAOYSA-N 4-ditert-butylphosphanyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 IQTHEAQKKVAXGV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011173 biocomposite Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 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
- 238000006396 nitration reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
本发明提供了一种二胺化合物、其中间体以及由其制成的聚酰亚胺薄膜。本发明二胺化合物具有式(1)或式(1A)所示的结构,其能够为聚酰亚胺带来更好的光学性能和耐高温性能,由其制成的聚酰亚胺薄膜一种性能良好的薄膜材料。
Description
技术领域
发明涉及聚合物领域,具体而言,本发明涉及一种二胺化合物、其中间体以及由其制成的聚酰亚胺薄膜。
背景技术
聚酰亚胺(polyimide,PI)被誉为“21世纪最有希望的工程塑料”之一,其为主链上带有酰亚胺环的一类高分子化合物。PI具有优异的耐热性能、机械性能、电绝缘性能、耐辐射性能以及良好的化学稳定性能,这使得其分别以薄膜、纤维、复合材料、光敏、泡沫、胶粘剂等广泛应用于电力电气、原子能工业、航空航天、国防军工等领域。
近年来,随着先进通信和电子社会的发展,人们对显示器或传感器等柔性设备的期望值越来越高。柔性基板是柔性显示器的重要组成部分,主要分为5类:塑料、金属箔片、超薄玻璃、纸质衬底、生物复合薄膜衬底。其中,塑料薄膜由于具有超薄、柔韧、可以逐卷生产等特点,是大型柔性面板制造的首选。而聚酰亚胺由于有高耐热性、高尺寸稳定性、良好的水蒸气传输速率和耐化学性等优异性能,在柔性基板中的研究应用已成为目前的开发热点,受到了各国研究人员的关注。
然而,常见的全芳族聚酰亚胺由于分子间和分子内产生的电荷转移络合物(CTC)而在可见光区域呈现出较深的颜色,影响其光学性能;同时其还存在玻璃化转变温度不够高的问题。为了实现聚酰亚胺耐高温性能和透明性能的平衡统一,有必要需要通过合理的分子设计,提供一种实现耐高温性能和透明性能的平衡统一的高性能聚酰亚胺。
发明内容
针对技术存在的上述问题,本申请提供了一种二胺化合物以及由其制成的聚酰亚胺薄膜,所述聚酰亚胺薄膜同时具有耐高温性能好和透明性好的优点。
在第一个方面,本发明提供了一种式(1)或式(1A)所示的二胺化合物:
。
本申请还提供一种合成式(1)或式(1A)所示的二胺化合物的中间体,其具有式(1-1)或式(1A-1)所示的结构:
。
本发明还提供了一种式(1)或式(1A)所示的二胺化合物的制备方法,其中,式(1)所示的二胺化合物的制备方法包括:
;
。
其中,步骤a包括:将式(1-0)或式(1A-0)所示的化合物溶于有机溶剂中,于10-40℃下缓慢滴加硝酸,然后于20℃-50℃下反应得到式(1-1)或式(1A-1)所示的中间体。
步骤b包括:将式(1-1)或式(1A-1)所示的中间体在催化剂存在下进行氢化还原,得到式(1)或式(1A)所示的二胺化合物。
优选的,步骤b的催化剂为Pd/C。
式(1-0)和式(1A-1)可以采用本领域已知的化学反应合成。
例如,式(1-0)可以采用以下方法合成:
具体地,2-溴-9,9,10,10-四甲基9,10-二氢菲和邻乙酰基苯硼酸在钯催化剂、碱存在下反应生成中间体(1-0-1);中间体(1-0-1)与甲基溴化镁反应生成中间体(1-0-2);中间体(1-0-2)在三氟甲磺酸的作用下环合生成式(1-0)。
优选的,所述碱为碳酸钠、碳酸氢钠、碳酸钾、碳酸氢钾、碳酸铯中的至少一种。
式(1A-0)可以采用以下方法合成:
化合物(1A-0-1)与碘甲烷在氢化钠作用下反应生成中间体(1A-0)。
本发明的第二个方面提供了一种聚酰亚胺,由芳香族二酐化合物和芳香族二胺化合物制备得到;所述芳香族二胺化合物包括上述式(1)或式(1A)所示化合物。
优选的,所述聚酰亚胺是聚酰亚胺薄膜。
优选的,所述芳香族二酐化合物选自式(2)或式(3)所示化合物:
其中环A和环B独立的选自取代或未取代的:苯环、萘环、蒽环、菲环;式(3)中环A和环B通过单键连接。
在一个实施方案中,所述取代或未取代是指未被取代,或者被选自C1-C12的烷基、C1-C12的烷氧基、C6-C20的芳香族烃基、卤素、CN的基团单取代或多取代。
优选的,所述C1-C12的烷基选自C1-C6的烷基,优选为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、己基。
优选的,所述C1-C12的烷氧基选自C1-C6的烷氧基,优选为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、己氧基。
优选的,所述C6-C20的芳香族烃基选自苯基、萘基、联苯基。
优选的,所述卤素选自氟、氯、溴、碘,优选为氟或氯。
进一步的,所述芳香族二酐化合物选自以下结构:
。
优选的,所述二酐化合物选自 。
本发明还提供了所述的聚酰亚胺的制备方法,包括以下步骤:
(1)将式(1)或式(1A)所示的二胺化合物和芳香族二酐化合物在有机溶剂中反应,得到聚酰胺酸溶液;
(2)将得到的聚酰胺酸溶液流延成膜,再依次进行烘干、亚胺化和固化,得到聚酰亚胺薄膜。
优选的,所述芳香族二酐化合物选自式(2)或式(3)所示化合物。
优选的,所述有机溶剂选自:乙酸乙酯、DMF、DME、DMSO、HMPA其中的一种或者二种的混合物。
优选的,所述式(1)或式(1A)所示的二胺化合物和芳香族二酐化合物的摩尔比为0.8:1~1:0 .8,优选为1:1。
优选的,式(1)或式(1A)所示的二胺化合物和芳香族二酐化合物在有机溶剂中反应,反应温度为-20~80℃,时间为3~48h。更优选的,反应温度为20~50℃,时间为6~18h。
优选的,所述烘干包括在150~200℃下烘干1~12h。
优选的,所述亚胺化是指在260~320℃下亚胺化0.5~5 h。
优选的,所述固化是指在340~400℃下固化0.5~3h。
有益效果:
本发明提供了一种二胺化合物、其中间体以及由其制成的聚酰亚胺薄膜。本发明的新颖的二胺化合物能够为聚酰亚胺带来更好的光学性能和耐高温性能,由其制成的聚酰亚胺薄膜一种性能良好的薄膜材料。
具体实施方式
以下将对发明的优选实例进行详细描述。所举实例是为了更好地对发明内容进行陈述,并不是发明内容仅限于实例。根据发明内容对实施方案的非本质的改进和调整,仍属于发明范畴。
下面实施例中的实验方法,如无特殊说明,均为常规方法。实施例中未注明具体技术或条件者,按照本领域内的文献所描述的技术或条件,或者按照产品说明书进行。
合成实施例1:化合物(1)的合成方法:
(1)中间体(1-0-1)的合成:
在氮气保护下向三口瓶中加入800 毫升甲苯,31.4克2-溴-9,9,10,10-四甲基9,10-二氢菲,17克邻乙酰基苯硼酸,20 g碳酸钠和1 g二氯二叔丁基-(4-二甲基氨基苯基)膦钯(II),加热至回流反应3小时,降温后加水分液,将有机层水洗后,用无水氯化钙干燥,除去干燥剂后,浓缩出溶剂,用乙醇结晶,得到31克中间体1-0-1。
对中间体(1-0-1)进行质谱检测,m/z为354.20。
(2)中间体(1-0-2)的合成:
氮气保护下,三口瓶中,加入35克中间体(1-0-1),500毫升四氢呋喃,降温至0-5℃,缓慢滴加甲基溴化镁的四氢呋喃溶液(浓度1.0M,200毫升),加毕升至室温反应1小时,再回流反应1小时,降温,加水和200毫升二氯甲烷分液,二氯甲烷层水洗至中性,无水硫酸镁干燥,滤去硫酸镁后,得到中间体(1-0-2)的二氯甲烷溶液,直接进行第三步反应。
(3)中间体(1-0)的合成:
中间体(1-0-2)的二氯甲烷溶液放入三口瓶中,氮气下,降温至5-10℃,缓慢滴加100克三氟甲磺酸,滴加过程中逐渐析出固体。加毕,于10-20℃搅拌反应4小时,加水,过滤,得到的固体用水洗、甲醇洗涤,干燥,得到18克中间体(1-0)。
对中间体(1-0)进行质谱检测,m/z为:352.22。
(b)化合物(1)的合成
(1)中间体(1-1)的合成:
1000毫升三口瓶中,加入35克原料(1-0),350毫升二氯甲烷,110毫升冰醋酸,搅拌下,于20℃缓慢滴加60%的硝酸水溶液26克,加毕于25℃-30℃反应6小时,加水分液,有机层水洗后,50℃水浴减压浓缩至干,乙醇结晶4次,得到7.1克中间体(1-1)。
对得到的中间体(1-1)进行质谱检测,m/z为:442.19。
测量了中间体(1-1)的核磁,数据如下:
(瑞士Bruker公司,AvanceⅡ400MHz核磁共振波谱仪,CDCl3),δ: 8.40 (d, 1H),8.37 (d,1H), 8.25 (m, 1H),8.19 (d, 1H),8.09 (s, 1H), 8.07-8.05 (m,2H), 7.93(d, 1H), 1.70 (s, 6H), 1.30 (s, 12H)。
(2)化合物(1)的合成:
500毫升高压釜中,加入按照上步方法制备得到的中间体(1-1) 5克,无水乙醇100毫升,5%的Pd/C 0.5克,氮气置换后,氢气置换,然后于氢气压力0.2MPa,温度60℃,进行氢化反应6小时。降温,滤去Pd/C 后,母液浓缩至干,然后甲醇重结晶,得到化合物(1)3.8克。
对得到的化合物(1)进行质谱检测,m/z为:382.24。
合成实施例2:化合物(1A)的合成方法:
三口瓶,氮气保护,加入28克化合物(1A-0-1),1000毫升二甲基亚砜,于20-30℃分配加入64克含量60%的氢化钠,然后缓慢升温至50℃,滴加230克碘甲烷,加毕于50℃反应4小时,再升温至80℃反应4小时,再升温至120℃反应60小时。降温,缓慢加入甲醇分解过量的氢化钠,确保氢化钠分解完毕后,加入水和甲苯分液,有机层水洗至中性,无水氯化钙干燥,然后滤去干燥剂,有机层浓缩,用硅胶层析分离,用石油醚洗脱,得到中间体(1A-0),质量8.1克。
对得到的化合物(1A-0)进行质谱检测,m/z为:394.27。
(b)化合物(1A)的合成
(1)中间体(1A-1)的合成:
参照中间体(1-1)的合成,只是将硝化反应的原料(1-0)替换为原料(1A-0)。
对得到的中间体(1A-1)进行质谱检测,m/z为:484.24。
(2)化合物(1A)的合成:
参照化合物(1)的合成,只是将氢化反应的原料中间体(1-1)替换为中间体(1A-1)。
对得到的化合物(1A)进行质谱检测,m/z为:424.29。
本发明所述二胺单体,具有5,5,6,6,12,12-六甲基-6,12-二氢-5H-吲哚并[1,2-b]菲和5,5,6,6,12,12,13,13-八甲基-5,6,12,13-四氢苯并[k]并四苯的母环结构,使得使用其制备得到的聚酰亚胺薄膜,耐高温性能和透明性均得到改善。
聚酰亚胺薄膜制备实施例1:
500毫升三口瓶,氮气保护,机械搅拌,加入0.01mol,化合物10.01mol,DMF(N,N-二甲基甲酰胺)80毫升,35℃下反应12小时得到淡黄色聚酰胺酸溶液;将得到的聚酰胺酸溶液涂布于玻璃板后,180℃烘干8小时,然后300℃亚胺化2小时,360℃固化1小时,得到聚酰亚胺薄膜。
用日本岛津的UV-1800分光光度计测量所得到的聚酰亚胺薄膜的吸收光谱,测试380nm、420nm、550nm下的光的透过率,详细见下表。
用美国TA公司的Q800DMA仪器以拉伸模式进行分析,测试得到的聚酰亚胺薄膜的玻璃化转变温度Tg,详细见下表。
聚酰亚胺薄膜制备实施例2-4:
参照酰亚胺薄膜制备实施例1的方法,制备以下聚酰亚胺薄膜,区别在于二胺化合物和二酐化合物不同,具体见下表:
聚酰亚胺薄膜对比实施例1-2
参照酰亚胺薄膜制备实施例1的方法,制备以下聚酰亚胺薄膜,区别在于二胺化合物不同,具体见下表:
由上表可以看出,与对比实施例1-2相比,根据本发明的聚酰亚胺薄膜具有明显更高的透光率,因此具有更好的光学性能;同时还具有更高的玻璃化转变温度,也即具有更好的耐热性。
Claims (7)
1.一种式(1)或式(1A)所示的二胺化合物:
。
2.一种式(1-1)或式(1A-1)所示的化合物:
。
3.一种式(1)或式(1A)所示的二胺化合物的制备方法,其中,式(1)所示的二胺化合物的制备方法包括:
;
式(1A)所示的二胺化合物的制备方法包括:
。
4.根据权利要求3所述的制备方法,其特征在于,步骤a包括:将式(1-0)或式(1A-0)所示的化合物溶于有机溶剂中,于10-40℃下缓慢滴加硝酸,然后于20℃-50℃下反应得到式(1-1)或式(1A-1)所示的中间体;
步骤b包括:将式(1-1)或式(1A-1)所示的中间体在催化剂存在下进行氢化还原,得到式(1)或式(1A)所示的二胺化合物。
5.一种聚酰亚胺,由芳香族二酐化合物和芳香族二胺化合物制备得到;所述芳香族二胺化合物包括式(1)或式(1A)所示的二胺化合物:
;
所述二酐化合物选自 。
6.根据权利要求5所述的聚酰亚胺,其特征在于,所述聚酰亚胺为聚酰亚胺薄膜。
7.根据权利要求6所述的聚酰亚胺的制备方法,包括以下步骤:
(1)将式(1)或式(1A)所示的二胺化合物和芳香族二酐化合物在有机溶剂中反应,得到聚酰胺酸溶液;
(2)将得到的聚酰胺酸溶液流延成膜,再依次进行烘干、亚胺化和固化,得到聚酰亚胺薄膜。
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