CN111518121B - Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor - Google Patents
Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor Download PDFInfo
- Publication number
- CN111518121B CN111518121B CN202010405967.3A CN202010405967A CN111518121B CN 111518121 B CN111518121 B CN 111518121B CN 202010405967 A CN202010405967 A CN 202010405967A CN 111518121 B CN111518121 B CN 111518121B
- Authority
- CN
- China
- Prior art keywords
- based oligomer
- aminobenzofurandione
- aminobenzene
- difurandione
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 230000005669 field effect Effects 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- -1 aminobenzene difurandione Chemical compound 0.000 claims abstract description 22
- 239000004065 semiconductor Substances 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 7
- AWDQWRIMXYAFIK-UHFFFAOYSA-N 4-amino-1-benzofuran-2,3-dione Chemical compound NC1=CC=CC2=C1C(C(O2)=O)=O AWDQWRIMXYAFIK-UHFFFAOYSA-N 0.000 claims description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011259 mixed solution Substances 0.000 claims description 16
- 238000006619 Stille reaction Methods 0.000 claims description 15
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 230000001681 protective effect Effects 0.000 claims description 7
- 238000009210 therapy by ultrasound Methods 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 230000005540 biological transmission Effects 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000003993 interaction Effects 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- 238000001338 self-assembly Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 29
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 21
- 229910052737 gold Inorganic materials 0.000 description 21
- 239000010931 gold Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000000137 annealing Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000012546 transfer Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000005530 etching Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 241000252506 Characiformes Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- 239000000969 carrier Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 239000003463 adsorbent Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 230000010512 thermal transition Effects 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005232 molecular self-assembly Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 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 1
- 239000002245 particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Images
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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
Abstract
The invention belongs to the technical field of semiconductor materials, and particularly relates to aminobenzofuran diketone-based oligomer, a preparation method and application thereof, and an organic field effect transistor. The aminobenzene difurandione-based oligomer contains aminobenzene difurandione groups, so that high hole mobility is provided for the aminobenzene difurandione-based oligomer, and an amino structure unit existing at the tail end of a chromophore of the aminobenzene difurandione groups can enable the aminobenzene difurandione-based oligomer to form intermolecular hydrogen bond interaction in a solid state, so that intermolecular self-assembly and ordered arrangement performance of the aminobenzene difurandione-based oligomer during formation of a semiconductor film is improved, and charge transmission performance of the aminobenzene difurandione-based oligomer is improved; in addition, the amino group is an electron-rich group, which is beneficial to constructing a donor-acceptor structure system and improving the intermolecular carrier transmission capability.
Description
Technical Field
The invention belongs to the technical field of semiconductor materials, and particularly relates to aminobenzofuran diketone-based oligomer, a preparation method and application thereof, and an organic field effect transistor.
Background
The organic pi-conjugated material has the advantages of easily adjustable structure, low manufacturing cost, solution-soluble processing and the like, and is well applied to the field of Organic Field Effect Transistors (OFETs).
In a semiconductor layer of an organic field effect transistor, carriers need to frequently migrate within a single molecule and between individual molecules, and in order to improve the mobility of the carriers, a great deal of effort is made by those skilled in the art. Wu (Wu T, Yu C, Guo Y, Liu H, Yu C, Fan Y, Liu Y, Synthesis, structures, and properties of thio [3,2-b ] thiophene and dithiophene bridged ligands derivatives and Their use in polymer backbones.J. Phys Chem C,2012,116:22655-22662) introduces sulfur and oxygen atoms in the polymer backbone through which an S … O bond is formed to interact to adjust the conjugated backbone, thereby increasing the charge mobility between molecules; deng (Deng Z, Hao X, Zhang P, Li L, Yuan X, Ai T, Bao W, Kou K, Donor-acceptor-donor molecules based on diketopyrrolopyrrole benzodipyrrolidone and naphthyridolone: organic crystal field-effect transistors, dyes and Pigmetsu 2019,162:883-887) and the like extend through a pi-conjugated system, increasing the charge transfer channel and thus increasing the transfer rate of carriers; in addition, other simple methods for enhancing intermolecular charge transfer capability exist, such as donor-acceptor type materials, fluorine atoms introduced into the main chain, molecular self-assembly, pi-pi conjugated system stacking, reduction of the spacing between adjacent molecules, regulation of crystal size, and the like. However, the above methods only improve the carrier mobility in one direction, and cannot achieve the intermolecular self-assembly property, the intermolecular ordered aggregation property, and the carrier mobility.
Disclosure of Invention
In view of the above, the present invention provides an aminobenzofuran dione based oligomer having excellent self-assembly characteristics of intermolecular hydrogen bonding, ordered aggregation characteristics between molecules, and carrier transport properties, which can significantly improve the performance of electronic devices.
In order to achieve the purpose of the invention, the invention provides the following technical scheme:
the invention provides an aminobenzofurandione group oligomer which has the following structure:
the invention also provides a preparation method of the aminobenzene difurandione oligomer in the technical scheme, which comprises the following steps:
dissolving aminobenzene difurandione and bithiophene substituted pyrrolopyrrole dione in a mixed solvent, and performing first anhydrous and anaerobic operation on the obtained mixed system to obtain a mixed solution;
and mixing the mixed solution with palladium tetratriphenylphosphine, and sequentially carrying out second anhydrous anaerobic operation, Stille coupling reaction and purification treatment to obtain the aminobenzofurandione group oligomer.
Preferably, the molar ratio of aminobenzofurandione to bithiophene-substituted pyrrolopyrroledione is (2.0-2.5): 1.
preferably, the mixed solvent includes toluene and N, N-dimethylformamide; the volume ratio of the toluene to the N, N-dimethylformamide is 4: 1.
preferably, the total concentration of the aminobenzofurandione and the bithiophene substituted pyrrolopyrroledione in the mixed solution is 17-20 g/L.
Preferably, the molar ratio of the bithiophene-substituted pyrrolopyrroledione to palladium tetratriphenylphosphine is 1: 0.05.
preferably, the temperature of the Stille coupling reaction is 110 ℃ and the time is 24 h.
Preferably, the first anhydrous anaerobic operation and the second anhydrous anaerobic operation are carried out by ultrasonic treatment on a system to be treated; the ultrasonic treatment is carried out under the condition of introducing protective gas.
The invention also provides the application of the aminobenzofuran diketone-based oligomer in the technical scheme or the aminobenzofuran diketone-based oligomer obtained by the preparation method in the technical scheme as a semiconductor material in an electronic device.
The invention also provides an organic field effect transistor, wherein in the organic field effect transistor, an organic semiconductor layer is the aminobenzofuran diketone-based oligomer obtained by the preparation method in the technical scheme or the aminobenzofuran diketone-based oligomer obtained by the preparation method in the technical scheme.
The invention provides an aminobenzofurandione group oligomer which has the following structure:
the aminobenzene difurandione-based oligomer contains aminobenzene difurandione groups, so that high hole mobility is provided for the aminobenzene difurandione-based oligomer, and an amino structure unit existing at the tail end of a chromophore of the aminobenzene difurandione groups can enable the aminobenzene difurandione-based oligomer to form intermolecular hydrogen bond interaction (NH … OC) in a solid state, so that intermolecular self-assembly and ordered arrangement performance of the aminobenzene difurandione-based oligomer during formation of a semiconductor film is improved, better molecular crystals are obtained, and charge transfer performance of the aminobenzene difurandione-based oligomer is improved; in addition, the amino group is an electron-rich group, which is beneficial to constructing a donor-acceptor structure system and improving the intermolecular carrier transmission capability.
In addition, the aminobenzene difuran diketone oligomer provided by the invention also has excellent molecular planarity, a strong pi-pi conjugated system and strong donor-acceptor exchange performance; excellent intermolecular and intramolecular charge transfer characteristics; excellent thermal stability and solubility.
The test results of the examples show that the hole mobility of the organic field effect transistor prepared by the solution method reaches 0.39cm by using the aminobenzofurandione group oligomer provided by the invention as a semiconductor layer, using an n-type doped silicon wafer subjected to surface treatment by octadecyl trichlorosilane as a grid electrode (the surface of the n-type doped silicon wafer contains silicon dioxide with the thickness of 300nm as an insulating layer) and gold as a source electrode and a drain electrode2V-1·s-1。
Drawings
FIG. 1 is a scheme showing the synthesis of aminobenzofurandione based oligomers;
FIG. 2 is a nuclear magnetic hydrogen spectrum of an aminobenzofurandione-based oligomer obtained in example 1;
FIG. 3 is a nuclear magnetic carbon spectrum of an aminobenzofurandione-based oligomer obtained in example 1;
FIG. 4 is a DSC of the aminobenzofurandione based oligomer obtained in example 1;
FIG. 5 is a TGA profile of an aminobenzofurandione based oligomer obtained in example 1;
fig. 6 is an output characteristic curve before annealing of the organic field effect transistor in application example 1;
FIG. 7 is a graph showing a transfer transmission characteristic before annealing of the organic field effect transistor in application example 1;
fig. 8 is an output characteristic curve after annealing of the organic field effect transistor in application example 1;
fig. 9 is a transfer transmission characteristic curve after annealing of the organic field effect transistor in application example 1.
Detailed Description
The invention provides an aminobenzofurandione group oligomer which has the following structure:
in the present invention, the chemical name of the aminobenzofurandione group oligomer is: 7,7'- (((1, 4-bis (2-ethylhexyl) -2, 5-dioxo-1, 2,4, 5-tetrahydropyrrolo [3,2-b ] pyrrole-3, 6-substituted) bis (thiophene-5, 2-substituted)) bis (4, 1-phenylene)) bis (3- (4- (ethylamino) phenyl) benzo [1,2-b:4,5-b' ] difuran-2, 6-dione).
In the present invention, the aminobenzofurandione based oligomer is dark blue in color; the melting temperature is 248 ℃, the recrystallization temperature is 170 ℃, and the thermal decomposition temperature is 369 ℃.
The invention also provides a preparation method of the aminobenzofurandione group oligomer in the technical scheme, which comprises the following steps:
dissolving aminobenzene difurandione and bithiophene substituted pyrrolopyrrole dione in a mixed solvent, and performing first anhydrous and anaerobic operation on the obtained mixed system to obtain a mixed solution;
and mixing the mixed solution with palladium tetratriphenylphosphine, and sequentially performing second anhydrous anaerobic operation, Stille coupling reaction and purification treatment to obtain the aminobenzofurandione group oligomer.
In the present invention, unless otherwise specified, each component in the preparation method is a commercially available product well known to those skilled in the art.
The preparation method comprises the steps of dissolving aminobenzene difurandione and bithiophene substituted pyrrolopyrrole dione in a mixed solvent, and carrying out first anhydrous and oxygen-free operation on an obtained mixed system to obtain a mixed solution.
The source of the aminobenzofurandione is not particularly limited in the present invention, and the aminobenzofurandione can be prepared by a method well known to those skilled in the art. In the present invention, the aminobenzofurandione is preferably prepared by a method described in "Z.Deng, K.Yang, L.Li, W.Bao, X.Hao, T.ai, K.Kou.solution processed air-stable p-channel organic crystalline field-effect transistors of Aminobenzodifuranone.dyes and Pigments,2018,151, 173-178". In the present invention, the bithiophene substituted pyrrolopyrroledione is preferably a commercially available product, and in the examples of the present invention, the bithiophene substituted pyrrolopyrroledione is available from sahn chemical technology (shanghai) ltd.
In the invention, the molar ratio of aminobenzofurandione to bithiophene-substituted pyrrolopyrroledione is preferably (2.0-2.5): 1, more preferably (2.1 to 2.4): 1. in the present invention, the mixed solvent preferably includes toluene and N, N-dimethylformamide; the volume ratio of toluene to N, N-dimethylformamide is preferably 4: 1. in the invention, the total concentration of aminobenzofurandione and bithiophene substituted pyrrolopyrroledione in the mixed solution is preferably 17-20 g/L, and more preferably 17.5-19.5 g/L.
In the present invention, the first anhydrous anaerobic operation method is preferably to perform the super-treatment on the system to be treatedPerforming acoustic treatment; the ultrasonic treatment is carried out under the condition of introducing protective gas. The frequency of the ultrasound is not particularly limited in the present invention, and an ultrasound frequency known to those skilled in the art may be used. In the present invention, the shielding gas is preferably N2. The flow rate of the shielding gas in the first anhydrous and anaerobic operation is not particularly limited, and is subject to sufficient exhaust to form an anhydrous and anaerobic condition, such as 10 sccm. In the present invention, the time of the first water-and oxygen-free operation is preferably 10 min. The invention removes oxygen and moisture present in the system by a first anhydrous and anaerobic operation.
After the mixed solution is obtained, the mixed solution is mixed with palladium tetratriphenylphosphine, and the second anhydrous anaerobic operation, the Stille coupling reaction and the purification treatment are sequentially carried out to obtain the aminobenzofurandione group oligomer.
In the present invention, the molar ratio of the bithiophene-substituted pyrrolopyrroledione to palladium tetratriphenylphosphine is preferably 1: 0.05. in the invention, preferably, palladium tetratriphenylphosphine is added into the mixed solution; in the invention, the addition of the tetratriphenylphosphine palladium to the mixed solution is preferably carried out under a protective gas condition; the shielding gas is preferably N2。
In the invention, the second anhydrous anaerobic operation method is preferably to carry out ultrasonic treatment on the system to be treated; the ultrasonic treatment is carried out under the condition of introducing protective gas. The frequency of the ultrasound is not particularly limited in the present invention, and may be an ultrasound frequency known to those skilled in the art. In the present invention, the shielding gas is preferably N2. The flow rate of the shielding gas in the second anhydrous and anaerobic operation is not particularly limited, and the flow rate is subject to sufficient exhaust to form an anhydrous and anaerobic condition, such as 10 sccm. In the present invention, the time of the second anhydrous anaerobic operation is preferably 5 min. The invention removes oxygen and moisture existing in the system through the second anhydrous anaerobic operation.
In the invention, the temperature of the Stille coupling reaction is preferably 110 ℃, and the time is preferably 24 h. In the present invention, the Stille coupling reaction is preferably performed under the condition of solvent reflux; the solvent reflux rate is not particularly limited in the invention, so that the temperature stability of the Stille coupling reaction can be ensured.
In the present invention, the purification treatment preferably comprises the steps of:
sequentially diluting and extracting the product of the Stille coupling reaction, and sequentially drying, carrying out solid-liquid separation, solvent removal treatment and column chromatography separation on the obtained organic phase to obtain the aminobenzofurandione group oligomer.
In the present invention, the diluent used in the dilution is preferably dichloromethane. In the invention, the volume ratio of the diluent to a product system obtained by Stille coupling reaction is preferably (7-10): 1.
in the present invention, the extraction preferably includes a first extraction and a second extraction performed in this order. In the present invention, the extractant in the first extraction is preferably a NaCl solution; the concentration of the NaCl solution is not particularly limited in the present invention, and a NaCl concentration known to those skilled in the art may be used. In the invention, the volume ratio of the extraction agent to the product system obtained by the Stille coupling reaction in each extraction is preferably (2-3): 1. in the present invention, the number of times of the first extraction is preferably 2 times. In the present invention, the object to be continuously treated selected after the first extraction is an organic phase.
In the present invention, the extractant in the second extraction is preferably water, and more preferably distilled water. In the invention, the volume ratio of the extraction agent to the product system obtained by the Stille coupling reaction in the second extraction is preferably (2-3): 1.
after the second extraction, the present invention dries the resulting organic phase. In the present invention, the drying agent is preferably anhydrous magnesium sulfate. The present invention is not particularly limited to the specific drying process, and the organic phase may be dried by a solid known to those skilled in the art. The invention removes the water in the organic phase by drying.
In the present invention, the solid-liquid separation is preferably filtration; the filtration is not particularly limited in the present invention, and filtration known to those skilled in the art may be employed.
The solvent removal treatment in the present invention is not particularly limited, and is carried out by a rotary evaporation method, for example, so as to remove the solvent. In the present invention, the apparatus used in the rotary evaporation method is preferably a rotary evaporator. The present invention is not particularly limited to the specific operation of the rotary evaporation method, and the solvent can be removed.
In the present invention, the eluent in the column chromatography separation preferably comprises n-hexane and dichloromethane; the volume ratio of the n-hexane to the dichloromethane is preferably 1: 4. in the invention, the adsorbent in the column chromatography separation is preferably silica gel; the silica gel is preferably silica gel powder; the particle size of the silica gel powder is preferably 200 meshes.
In the present invention, the scheme for the synthesis of the aminobenzofurandione group oligomer is shown in FIG. 1.
The invention also provides the application of the aminobenzofuran diketone-based oligomer in the technical scheme or the aminobenzofuran diketone-based oligomer obtained by the preparation method in the technical scheme as a semiconductor material in an electronic device.
The invention also provides an organic field effect transistor, wherein the surface of a substrate is coated with the aminobenzofurandione-based oligomer in the technical scheme or the aminobenzofurandione-based oligomer obtained by the preparation method in the technical scheme.
In the present invention, the organic field effect transistor is preferably a bottom gate bottom contact field effect transistor.
In the present invention, the method for manufacturing the organic field effect transistor preferably includes the steps of:
providing a Si wafer substrate; the Si wafer substrate is attached with SiO on one side2A layer;
sequentially carrying out piranha etching solution etching, deionized water washing and acetone washing on the Si wafer substrate, placing the Si wafer substrate in a toluene solution of octadecyl trichlorosilane, and carrying out surface treatment to obtain a primary substrate;
forming a gold source electrode and a gold drain electrode on one surface of the silicon dioxide layer of the obtained primary substrate by adopting a mask gold spraying method to obtain a secondary substrate;
and coating the aminobenzofuran diketone-based oligomer in the technical scheme on the gold source electrode and the gold drain electrode of the secondary substrate, and sequentially standing, removing the solvent and annealing to obtain the organic field effect transistor.
The operation parameters in the preparation method of the organic field effect transistor are not particularly limited, and the process parameters known by the technical personnel in the field can be adopted, and specifically, the preparation of the organic field effect transistor can be carried out according to the following preparation method.
The present invention provides a Si wafer substrate; the Si wafer substrate is attached with SiO on one side2And (3) a layer.
In the present invention, the Si wafer substrate is preferably n-type doped Si (n)++) A wafer. In the present invention, SiO is attached to the Si wafer substrate2The thickness of the layer is preferably 300 nm. In an embodiment of the present invention, the Si wafer substrate is purchased from Silicon Quest International. In the present invention, the silicon layer serves as a gate, SiO2The layer serves as a dielectric layer.
After the Si wafer substrate is obtained, the Si wafer substrate is sequentially subjected to piranha etching solution etching, deionized water washing and acetone washing, and then placed in a toluene solution of octadecyl trichlorosilane for surface treatment to obtain a primary substrate.
In the invention, the volume ratio of sulfuric acid to hydrogen peroxide in the piranha etching solution is preferably 3: 1; the concentration of the sulfuric acid in the piranha etching solution is not particularly limited, and the sulfuric acid concentration known to those skilled in the art can be adopted. The present invention has no special limitation on the piranha etching solution, the deionized water washing and the acetone washing, and the present invention adopts the process known to those skilled in the art. In the present invention, the octadecyl trichlorosilane content in the toluene solution of octadecyl trichlorosilane is preferably 5% by mass. In the present invention, the surface treatment is preferably performed under a protective gas condition; the shielding gas is preferably argon. In the present invention, the time for the surface treatment is preferably 18 hours.
After the primary substrate is obtained, a gold source electrode and a gold drain electrode are formed on one surface of the silicon dioxide layer of the obtained primary substrate by adopting a mask gold spraying method, so that a secondary substrate is obtained.
The method for spraying gold on the mask is not particularly limited, and the method for spraying gold on the mask, which is well known to those skilled in the art, can be adopted. In the present invention, the thickness of the gold source electrode and the gold drain electrode is independently preferably 30 nm. In the present invention, the conductive trenches on the secondary substrate preferably have a length of 1000 μm and a width of 30 μm.
After the secondary substrate is obtained, the surfaces of a gold source electrode and a gold drain electrode of the secondary substrate are coated with the aminobenzofuran diketone-based oligomer in the technical scheme, and standing, solvent removal and annealing are sequentially carried out to obtain the organic field effect transistor.
In the invention, the coating amount of the aminobenzofuran diketone-based oligomer on the surface of the secondary substrate is preferably 3-4 drops; the coating amount is not limited to the area of the secondary substrate surface. In the present invention, the aminobenzofurandione based oligomer is preferably provided in the form of a chloroform solution of the aminobenzofurandione based oligomer; the concentration of the chloroform solution of the aminobenzofurandione group oligomer is preferably 5 mg/mL.
In the invention, the temperature of the standing is preferably room temperature, and specifically, 18-30 ℃; the time is preferably 0.5 h.
In the present invention, the solvent is removed preferably by constant temperature evaporation; the constant-temperature evaporation temperature is preferably 50 ℃, and the time is preferably 1 h. In the present invention, the annealing is preferably performed under a protective gas condition; the shielding gas is preferably argon. In the present invention, the annealing temperature is preferably 230 ℃ and the annealing time is preferably 5 min. The invention is beneficial to the hydrogen bond interaction between amino (NH) and carbonyl (C ═ O) of adjacent molecules through annealing, so that aminobenzofurandione-based oligomer forms better crystallinity and more ordered accumulation; good ordered packing facilitates the transfer of charge carriers between individual molecules in a thin film formed from the aminobenzofurandione based oligomer.
In order to further illustrate the present invention, the aminobenzofurandione-based oligomer, the preparation method and the application thereof, and the organic field effect transistor provided by the present invention will be described in detail with reference to the following examples, which should not be construed as limiting the scope of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Aminobenzodifurandione: prepared according to the document "Z.Deng, K.Yang, L.Li, W.Bao, X.Hao, T.ai, K.Kou.solvent processed air-stable p-channel organic crystalline field-effect transistors of amino benzofurannes and Pigments,2018,151,173-,
bithiophene substituted pyrrolopyrrolediones: from sahn chemical technology (shanghai) ltd, palladium tetratriphenylphosphine: purchased from sahn chemical technology (shanghai) ltd;
152.6mg (0.33mmol) of aminobenzofurandione and 127.5mg (0.15mmol) of bithiophene-substituted pyrrolopyrroledione are dissolved in 15mL of a mixed solvent of toluene and N, N-dimethylformamide in a volume ratio of 4: 1 is mixed, and the mixed system is N with the flow rate of 10sccm2Performing a first anhydrous oxygen-free operation for 10min under the ultrasonic condition to obtain a mixed solution;
in N28mg (0.0075mmol) of tetrakistriphenylphosphine palladium were rapidly added to the mixed solution at room temperature under a flow rate of 10sccm of N2After the second anhydrous anaerobic operation is carried out for 5min under the ultrasonic condition, the solvent is refluxed for 24h at 110 ℃ for Stille coupling reaction, and the system is naturally cooled to room temperature after the reaction is finished;
adding 100mL of dichloromethane into the product of the Stille coupling reaction for dilution to obtain a blue solution, sequentially extracting the obtained blue solution by adopting 100mL of 20% NaCl solution by mass, 100mL of 20% NaCl solution by mass and distilled water, then drying the organic phase obtained after extraction by adopting anhydrous magnesium sulfate, filtering and evaporating the solvent to obtain a crude product; and (3) separating the crude product by column chromatography, wherein the eluent is a mixture of eluent and water in a volume ratio of 1: 4, a mixed solvent of normal hexane and dichloromethane, and an adsorbent of 200-mesh silica gel powder, and finally separating to obtain the aminobenzofurandione-based oligomer.
The resulting aminobenzofurandione based oligomer was subjected to the following tests:
1. performing nuclear magnetic detection on the obtained aminobenzofuran diketone-based oligomer by a Mercury 300 nuclear magnetic resonance spectrometer, wherein the detection result is as follows:
1H-NMR(500MHz,CDCl3)δppm:8.92-9.01(t,2H,J＝5Hz),7.90(d,2H,J＝5Hz),7.79-7.84(m,4H),7.63-77.69(m,4H),7.35-7.57(m,4H),6.68-6.98(m,4H),4.29(s,1H),3.93-4.12(br,4H),3.27-3.30(t,3H,J＝15Hz,),1.95(s,2H),1.25-1.41(m,24),0.88-0.94(m,12H).13C NMR:δppm:132.55,132.32,131.31,130.16,129.45,129.13,126.40,126.30,125.34,119.00,112.93,99.30,97.20,96.87,45.96,39.25,37.91,30.31,28.08,23.65,23.08,14.59,14.30,10.59。
the nuclear magnetic hydrogen spectrum is shown in figure 2; the nuclear magnetic carbon spectrum is shown in FIG. 3. As can be seen from FIGS. 2 and 3, the aminobenzofurandione-based oligomer obtained by the present invention.
2. The obtained aminobenzofurandione-based oligomer was subjected to Differential Scanning Calorimetry (DSC) measurement by a Netzsch DSC (204F1) instrument under conditions of a temperature change rate of 10 deg.C/min and a nitrogen gas blowing rate of 20mL/min through a cyclic heating and cooling process, and the measurement results are shown in FIG. 4.
As can be seen from FIG. 4, the melting point temperature (T) of the resulting aminobenzofurandione-based oligomerm) At 248 ℃ and a recrystallization temperature (T)c) 170 deg.c and this thermal transition disappears in the second heating cycle. This is probably due to the mobility of the oligomers during the thermal annealing due to the temperature increase and relatively weak intermolecular interactions. At the same time, the donor unit (NH) forms a hydrogen bond with the acceptor unit (C ═ O),the same hydrogen bond crosslinks are formed as in the aminobenzofurandione based oligomer, which shows thermal stability without any thermal transition.
3. And (3) thermogravimetric analysis detection: the detection is carried out by using a Netzsch TGA (209F1) thermogravimetric analyzer, and the detection chart is shown in figure 5.
As can be seen from FIG. 5, the resulting aminobenzofuranedione-based oligomer showed no weight loss by heat before 320 ℃ and a weight loss of 5% at 369 ℃, indicating that the aminobenzofuranedione-based oligomer provided had a higher thermal stability.
As can be seen from FIGS. 4 and 5, the aminobenzofurandione-based oligomer provided by the present invention has good processability and thermal stability.
Application example 1
Si wafer substrate: from Silicon Quest International, N-type doped Si (n)++) A wafer having 300nm SiO attached to its surface2A layer;
preparing an organic field effect transistor by adopting a bottom-gate bottom-contact field effect transistor structure:
selected n-type doped Si (n)++) A wafer as a substrate, wherein the silicon layer is used as a gate electrode, SiO2The layer is used as a dielectric layer; sequentially etching Si wafer substrate with piranha etching solution (H)2SO4/H2O23/1, volume ratio), deionized water washing, acetone washing, and soaking in 5 wt.% toluene solution of octadecyl trichlorosilane under the protection of argon at room temperature for 18 h; forming a gold source electrode and a gold drain electrode on the silicon chip by a mask gold spraying method, wherein the thickness of the gold source electrode and the thickness of the gold drain electrode are both 30nm, the length of the conductive groove is 1000 microns, and the width of the conductive groove is 30 microns; then, under the protection of argon, 3-4 drops of chloroform solution of aminobenzofuran diketone oligomer of 5mg/mL are dripped on the surface of the substrate of the treated gold electrode at one time; standing at room temperature for 0.5h, heating to 45 deg.C for 1h, and removing solvent; and finally, annealing the device for 5min at 230 ℃ under the protection of argon to obtain the organic field effect transistor based on the aminobenzofurandione-based oligomer.
Respectively carrying out an output characteristic test and a transfer characteristic test on the obtained organic field effect transistor before and after annealing, wherein test graphs are shown in fig. 6-9, and fig. 6 is an output characteristic curve of the organic field effect transistor before annealing; FIG. 7 is a graph of transfer characteristics of an organic field effect transistor prior to annealing; FIG. 8 is an output characteristic curve after annealing of an organic field effect transistor; fig. 9 is a transfer transmission curve after annealing of the organic field effect transistor.
As can be seen from FIGS. 6-9, the aminobenzofuran dione based oligomer showed p-type device characteristics before annealing, and the hole mobility was up to 0.28cm2V-1s-1On-off ratio Ion/IoffAbout 106. The reason for the high hole mobility is probably due to the pi-conjugated backbone and coplanar molecular conformation of O1 molecules in the D-A system, which not only enhances the transport of charges in the molecules, but also ensures the close packing of the molecules through the D-A dipole-dipole interaction between the molecules. In addition, strong interactions are also responsible for the high carrier mobility between molecules. After annealing, the hole mobility value of the resulting transistor was increased to 0.39cm2 V- 1s-1On-off ratio Ion/IoffIs still 106And the carrier mobility is good.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. An aminobenzofurandione based oligomer having the following structure:
2. a process for the preparation of the aminobenzofurandione based oligomer according to claim 1, comprising the steps of:
dissolving aminobenzene difurandione and bithiophene substituted pyrrolopyrrole dione in a mixed solvent, and performing first anhydrous and anaerobic operation on the obtained mixed system to obtain a mixed solution;
mixing the mixed solution with palladium tetratriphenylphosphine, and sequentially carrying out second anhydrous anaerobic operation, Stille coupling reaction and purification treatment to obtain the aminobenzofurandione group oligomer;
the aminobenzofurandione has a structure shown in formula I:
formula I;
the bithiophene substituted pyrrolopyrroledione has a structure shown in formula II:
formula II.
3. The preparation method according to claim 2, wherein the molar ratio of aminobenzofurandione to bithiophene-substituted pyrrolopyrroledione is (2.0 to 2.5): 1.
4. the production method according to claim 2, wherein the mixed solvent is toluene and N, N-dimethylformamide; the volume ratio of the toluene to the N, N-dimethylformamide is 4: 1.
5. the preparation method according to claim 2, wherein the total concentration of the aminobenzofurandione and the bithiophene-substituted pyrrolopyrroledione in the mixed solution is 17 to 20 g/L.
6. The method according to claim 2 or 5, wherein the molar ratio of the bithiophene-substituted pyrrolopyrroledione to tetratriphenylphosphine palladium is 1: 0.05.
7. the preparation method according to claim 2, wherein the temperature of the Stille coupling reaction is 110 ℃ and the time is 24 h.
8. The method for preparing according to claim 2, wherein the first anhydrous anaerobic operation and the second anhydrous anaerobic operation are performed by ultrasonic treatment of a system to be treated; the ultrasonic treatment is carried out under the condition of introducing protective gas.
9. Use of the aminobenzofurandione based oligomer according to claim 1 as a semiconductor material in electronic devices.
10. An organic field-effect transistor, wherein an organic semiconductor layer is the aminobenzofuran dione based oligomer according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010405967.3A CN111518121B (en) | 2020-05-14 | 2020-05-14 | Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010405967.3A CN111518121B (en) | 2020-05-14 | 2020-05-14 | Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111518121A CN111518121A (en) | 2020-08-11 |
| CN111518121B true CN111518121B (en) | 2022-05-13 |
Family
ID=71907794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010405967.3A Active CN111518121B (en) | 2020-05-14 | 2020-05-14 | Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111518121B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115863651B (en) * | 2022-12-29 | 2024-10-18 | 蜂巢能源科技股份有限公司 | In-situ coated high-voltage positive electrode material, preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108948329A (en) * | 2018-06-12 | 2018-12-07 | 合肥工业大学 | A kind of conjugated polymer semiconductor material of ultralow energy level and preparation method thereof |
| CN110862517A (en) * | 2018-08-28 | 2020-03-06 | 北京大学 | Rigid conjugated polymer based on benzodifurandione and derivatives thereof, preparation and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11183638B2 (en) * | 2018-05-29 | 2021-11-23 | Purdue Research Foundation | Semiconducting polymer blends for high temperature organic electronics |
-
2020
- 2020-05-14 CN CN202010405967.3A patent/CN111518121B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108948329A (en) * | 2018-06-12 | 2018-12-07 | 合肥工业大学 | A kind of conjugated polymer semiconductor material of ultralow energy level and preparation method thereof |
| CN110862517A (en) * | 2018-08-28 | 2020-03-06 | 北京大学 | Rigid conjugated polymer based on benzodifurandione and derivatives thereof, preparation and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| π-Conjugated oligomers based on aminobenzodifuranone and diketopyrrolopyrrole;Haichang Zhang et al.;《Dyes and Pigments》;20200519;第181卷;第1-7页 * |
| 氧敏感性供体-受体共轭聚合物薄膜晶体管;薛战等;《发光学报》;20180831;第39卷(第8期);第1136-1142页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111518121A (en) | 2020-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhong et al. | Air‐Stable and High‐Mobility n‐Channel Organic Transistors Based on Small‐Molecule/Polymer Semiconducting Blends | |
| EP2710012B1 (en) | Organic semiconductor material | |
| TW200904821A (en) | Silylethynylated heteroacenes and electronic devices made therewith | |
| CN108864137B (en) | Receptor compound, preparation method and application thereof, and photovoltaic cell containing receptor compound | |
| Dai et al. | Diacenopentalene dicarboximides as new n-type organic semiconductors for field-effect transistors | |
| Gao et al. | Dibenzotetrathiafulvalene bisimides: new building blocks for organic electronic materials | |
| Shaker et al. | Face-on oriented thermolabile Boc-isoindigo/thiophenes small molecules: From synthesis to OFET performance | |
| Zhou et al. | Diketopyrrolopyrrole-based small molecules for solution-processed n-channel organic thin film transistors | |
| KR102001455B1 (en) | Semiconductor composition | |
| WO2011047624A1 (en) | Sulfur containing heterocycle-fused naphthalene tetracarboxylic acid diimide derivatives, preparation method and use thereof | |
| CN111518121B (en) | Aminobenzofuran diketone-based oligomer, preparation method and application thereof, and organic field effect transistor | |
| TWI580020B (en) | Perylene-based semiconductors and methods of preparation and use thereof | |
| EP3110807B1 (en) | Heteroacenes for organic electronics | |
| Li et al. | High-performance electron-transporting hybrid rylenes with low threshold voltage | |
| Lee et al. | Synthesis and characterization of fluorenone-based donor-acceptor small molecule organic semiconductors for organic field-effect transistors | |
| CN114195698B (en) | Imide fluoranthene molecular building block, preparation and application thereof | |
| CN114933609B (en) | N-type organic semiconductor material based on isoindigo fluorine boron hybridization, preparation method thereof and organic field effect transistor | |
| CN109749058B (en) | Anthracene bithiophene imide polymer and preparation method and application thereof | |
| Koh et al. | Synthesis and characterization of novel p-type alkyl bithiophene end-capped anthracene and naphthalene derivatives for organic thin-film transistors | |
| CN112442169B (en) | Asymmetric isoindigo receptor and polymer, and preparation method and application thereof | |
| Giri et al. | Ambient stable solution-processed organic field effect transistors from electron deficient planar aromatics: effect of end-groups on ambient stability | |
| CN109942585B (en) | Organic semiconductor material, preparation method, field effect transistor device and manufacturing method thereof | |
| CN112851916B (en) | Aromatic heterocyclic conjugated polymer based on benzofuranone, preparation method and application thereof, and organic field effect transistor | |
| CN115947727B (en) | Preparation method and application of aza-olympic alkene dye molecule | |
| KR101390666B1 (en) | Diketopyrrolopyrrole- and tellurophene-based polymers derivative, organic semiconductor thin film and organic thin film transistor comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |