CN112778339A - Polythiophene dianhydride compound and synthesis method thereof - Google Patents
Polythiophene dianhydride compound and synthesis method thereof Download PDFInfo
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- CN112778339A CN112778339A CN202110170806.5A CN202110170806A CN112778339A CN 112778339 A CN112778339 A CN 112778339A CN 202110170806 A CN202110170806 A CN 202110170806A CN 112778339 A CN112778339 A CN 112778339A
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- thiophene
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- dianhydride
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- 229920000123 polythiophene Polymers 0.000 title claims abstract description 17
- -1 dianhydride compound Chemical class 0.000 title claims description 12
- 238000001308 synthesis method Methods 0.000 title abstract description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000004642 Polyimide Substances 0.000 claims abstract description 29
- 229920001721 polyimide Polymers 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 229930192474 thiophene Natural products 0.000 claims abstract description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 14
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 239000010703 silicon Substances 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 4
- NRIMHVFWRMABGJ-UHFFFAOYSA-N bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid Chemical compound C1C2C(C(=O)O)=C(C(O)=O)C1C=C2 NRIMHVFWRMABGJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 229920001088 polycarbazole Polymers 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229940126214 compound 3 Drugs 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical group C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012660 binary copolymerization Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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- 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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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a compound containing polythiophene dianhydride and a synthesis method thereof, wherein the structure of the compound is as follows:
Description
Technical Field
The invention belongs to the technical field of polyimide materials, and particularly relates to a compound containing polythiophene dianhydride and a synthesis method thereof.
Background
3, 6-di (2, 3-thiophene anhydride) thiophene is a novel dianhydride compound containing polythiophene, has good electron donor, and can be polymerized with various amine compounds to produce polyimide. Polyimide has excellent properties such as high strength, low dielectric, high modulus, high temperature resistance, radiation resistance and the like, is concerned, and has wide application prospect and great commercial value in a plurality of high and new technical fields such as aerospace, aviation, space, microelectronics, precise machinery, medical appliances, organic light-emitting and electricity-generating materials, optical storage and the like.
Polyimide is generally prepared from dianhydride and diamine through binary copolymerization, and different monomer structures determine various properties of polyimide materials, so the research and development of polyimide monomer raw materials are a prerequisite condition for developing novel polyimide materials. At present, polyimides with single performance are very common, and how to develop a polyimide with multiple functional properties at the same time is an important subject of polyimide research at present.
The fluorine-containing polycarbazolyl is a good electron donor with aromaticity, is easy to form a D-pi-A system, and has high electron density and good rigid structure. According to the invention, N-phenyl carbazole group is used for constructing the dianhydride compound, and then the dianhydride compound and diamine monomer are used for preparing the polyimide, so that the electron-donating capability of a dianhydride structure can be enhanced, the molecular delocalization is increased, and the polyimide has excellent storage performance and photoelectric performance.
Disclosure of Invention
The invention aims to improve the performance of a polyimide material, and provides a dianhydride compound containing a polythiophene structure and having high planarity and a synthesis method thereof.
The invention aims to realize the purpose, and the compound containing polythiophene dianhydride is characterized in that the structure of the compound is as follows:
In order to achieve the object of the present invention, the fluorine-containing polycarbozole-containing thiadiazole isThe thiophene dianhydride compound adopts the following synthetic route:
the preparation method comprises the steps of taking 3, 6-di (2, 3-dicarboxylic acid thiophene) thiophene shown in a structure I as a raw material, taking organic solvents such as acetic acid, acid anhydride and the like as reaction media, heating to reflux and preserving heat for 5-10 hours in an oxygen-free environment under the catalysis of a silicon-based solid dehydrating agent SH-01 to obtain corresponding polythiophene-containing compound II 3, 6-di (2, 3-thiophene anhydride) thiophene, filtering and recrystallizing after the reaction is finished, wherein omega II is purified to be more than 98%, and the reaction yield is more than 50%.
In order to further achieve the purpose of the invention, the organic solvent may be one or more of acetic acid, acetic anhydride, trifluoroacetic anhydride, xylene, tetrahydrofuran, and the like.
In order to further realize the purpose of the invention, the reaction temperature can be 30-150 ℃, and the reaction time can be 5-10 h.
According to the invention, when the structure of the compound is designed, the dianhydride compound containing polythiophene is designed and synthesized, and the dianhydride is used for preparing the polyimide containing polythiophene, so that the polyimide has excellent storage performance and good photoelectric performance. The invention has the following beneficial effects:
1. according to the invention, polythiophene groups containing strong intramolecular electron transfer are introduced into the dianhydride compound, and after polyimide is synthesized, the electron transfer capacity is greatly improved.
2. The dianhydride compound synthesized by the invention and the diamine monomer are polymerized to generate polyimide, and the polyimide has good thermal stability.
3. The data for the compounds of the invention compared to BPDA are shown in the following table:
| name of Compound | Molecular weight | Boiling point/. degree.C | Melting Point/. degree.C |
| BPDA | 294.22 | 609 | 199 |
| Ⅱ | 688.75 | 820 | 310 |
Detailed Description
The present invention is further illustrated by the following examples, which are included merely for the purpose of clarity and are not intended to limit the invention.
A compound containing polythiophene dianhydride has the following structure:
，
the synthetic route is as follows:
The electron withdrawing effect of the dianhydride group and the electron donating effect of the diamine group form an electron transfer complex effect (CTC), and the charge transfer effect in molecules or between molecules causes the film to show brown yellow in a visible light range. The introduction of the group containing carbazole dianhydride can inhibit the formation of CTC and improve various properties of the PI material; the thiophene group is introduced, so that the thermal stability of the PI material can be improved on the basis of not influencing the light transmittance;
n-phenylcarbazole-2, 2，The copolymerization type fluorine-containing Polyimide (PI) film is synthesized by 3,3 ' -dianhydride monomer, 4' -diamino-2, 2' -bistrifluoromethyl biphenyl monomer and 3, 6-di (2, 3-thiophene anhydride) thiophene according to a certain proportion, has good photoelectric property, has light transmittance of more than 85% in a visible light region, and has good thermal stability at 500-600 ℃, and the copolymerization type fluorine-containing Polyimide (PI) film synthesized by N-phenylcarbazole-2, 2', 3,3 ' -dianhydride monomer and 4,4' -diamino-2, 2' -bistrifluoromethyl biphenyl monomer has light transmittance of 85% and relatively poor thermal stability at 500-600 ℃; the PI material formed by the dianhydride and the diamine can be used for coating, namely as insulating paint for electromagnetic wires or as high-temperature resistant coating;
and (3) product structure confirmation: the elemental analysis measured values were w (c) = 69.70%, w (h) =2.39%, w(s) = 13.90%, w (o) = 14.01%; theoretical values w (c) = 69.75%, w (h) = 2.34%, w(s) =13.97%, w (o) = 13.94%; melting Point>470℃；MS：m/s= 688.75（M+)。
Claims (5)
1. A fluorine-containing polycarbazole-containing thiophene dianhydride compound is characterized in that the structure of the compound is as follows:
2. A method for synthesizing a compound containing polythiophene dianhydride according to claim 1, which is characterized by adopting the following synthetic route:
the method comprises the steps of taking 3, 6-di (2, 3-dicarboxylic acid thiophene) thiophene shown in a structure I as a raw material, taking an organic solvent as a reaction medium, heating to reflux and preserving heat for 5-10 hours in an oxygen-free environment under the catalysis of a silicon-based solid dehydrating agent SH-01 to obtain corresponding dianhydride compound II 3, 6-di (2, 3-thiophene anhydride) thiophene containing polythiophene, filtering and recrystallizing after the reaction is finished, wherein omega II is purified to be more than 98%, and the reaction yield is more than 50%.
3. The method for synthesizing the compound containing polythiophene dianhydride according to claim 2, wherein the organic solvent is one or more of acetic acid, acetic anhydride, trifluoroacetic anhydride, xylene and tetrahydrofuran.
4. The method for synthesizing the compound containing polythiophene dianhydride according to claim 2, wherein the reaction temperature is 30-150 ℃ and the reaction time is 5-10 hours.
5. The use of the compound containing polythiophene dianhydride according to claim 1 in the field of polyimide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202110170806.5A CN112778339A (en) | 2021-02-08 | 2021-02-08 | Polythiophene dianhydride compound and synthesis method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110170806.5A CN112778339A (en) | 2021-02-08 | 2021-02-08 | Polythiophene dianhydride compound and synthesis method thereof |
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| CN112778339A true CN112778339A (en) | 2021-05-11 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101503398A (en) * | 2009-03-17 | 2009-08-12 | 成都金桨高新材料有限公司 | Novel sulfide or sulfone containing dianhydride, and preparation and use thereof |
| CN104478838A (en) * | 2014-11-28 | 2015-04-01 | 吉林大学 | Phenylethynyl-containing dianhydride monomer, and synthesis method and application thereof |
| CN109438470A (en) * | 2018-12-24 | 2019-03-08 | 山东盛华新材料科技股份有限公司 | One kind is containing two compound anhydride of thiophene and its synthetic method and application |
-
2021
- 2021-02-08 CN CN202110170806.5A patent/CN112778339A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101503398A (en) * | 2009-03-17 | 2009-08-12 | 成都金桨高新材料有限公司 | Novel sulfide or sulfone containing dianhydride, and preparation and use thereof |
| CN104478838A (en) * | 2014-11-28 | 2015-04-01 | 吉林大学 | Phenylethynyl-containing dianhydride monomer, and synthesis method and application thereof |
| CN109438470A (en) * | 2018-12-24 | 2019-03-08 | 山东盛华新材料科技股份有限公司 | One kind is containing two compound anhydride of thiophene and its synthetic method and application |
Non-Patent Citations (1)
| Title |
|---|
| V. É. KAMPAR，ET AL.，: ""Effect of the heteroatom on the energies of the boundary molecular orbitals of dibenzo derivatives of five-membered heterocycles"", 《CHEMISTRY OF HETEROCYCLIC COMPOUNDS》 * |
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Application publication date: 20210511 |