CN115197219B - Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof - Google Patents
Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof Download PDFInfo
- Publication number
- CN115197219B CN115197219B CN202110381085.2A CN202110381085A CN115197219B CN 115197219 B CN115197219 B CN 115197219B CN 202110381085 A CN202110381085 A CN 202110381085A CN 115197219 B CN115197219 B CN 115197219B
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- preparation
- field effect
- perylene diimide
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 title claims abstract description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 6
- 230000005669 field effect Effects 0.000 claims abstract description 24
- 239000004065 semiconductor Substances 0.000 claims abstract description 15
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 69
- 239000000463 material Substances 0.000 claims description 21
- 150000003384 small molecules Chemical class 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000007039 two-step reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 125000000217 alkyl group Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 6
- -1 perylene imide Chemical class 0.000 description 6
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229940125773 compound 10 Drugs 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000004896 high resolution mass spectrometry Methods 0.000 description 5
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000010200 validation analysis Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- KRSBPXGBUCAYSC-UHFFFAOYSA-N azulene benzene Chemical group C1=CC=CC=C1.C1=CC=C2C=CC=CC=C12 KRSBPXGBUCAYSC-UHFFFAOYSA-N 0.000 description 3
- 150000001545 azulenes Chemical class 0.000 description 3
- 125000003828 azulenyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 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
- 238000010998 test method Methods 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electromagnetism (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a perylene diimide conjugated fused ring molecule containing azulene, a preparation method thereof and application thereof in the field of field effect transistors. The structural formula is shown as formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 As shown. The perylene diimide condensed ring system with near infrared absorption containing azulene is obtained through two-step reaction separation, which all show p-type semiconductor performance, and the hole mobility of 7 and 10 respectively reach 10 ‑ 4 cm 2 V ‑1 s ‑1 And 4X 10 ‑3 cm 2 V ‑1 s ‑1 And has near infrared absorption characteristics.
Description
Technical Field
The invention belongs to the field of organic synthesis and photoelectric materials, and particularly relates to preparation of perylene diimide conjugated fused ring molecules containing azulene, exploration of photophysical properties and application thereof in the field of field effect transistors.
Background
Polymer semiconductor materials have been studied relatively well over the past few decades, and many have achieved amorphous silicon levels in mobility. However, the polymer has limited application in device research because of inaccurate measurement of its composition, structure, stacking mode, etc. In comparison, small organic molecules are increasingly being used for mechanism research in carrier transport processes due to their specific structure and composition. For example, some small molecular backbones such as pyrrolopyrrole Dione (DPP), naphthalimide (NDI), perylene Diimide (PDI) have been widely used and gradually developed into star molecules. Therefore, the development of novel structurally defined small molecular frameworks is of great significance for the understanding of the mechanism and the development of materials of organic semiconductors.
Non-benzene molecular azulenes condensed from five-and seven-membered rings are receiving increasing attention in organic field effect transistors due to their unique chemical structure and electron distribution characteristics. The introduction of the azulene ring can greatly change the planeness, electron distribution, dipole and other characteristics of the conjugated framework, thereby changing the photophysical and semiconductor performances of the semiconductor. Therefore, the azulene unit is combined with a plurality of rigid semiconductor frameworks, the photoelectric property of the molecule is regulated and controlled through the expansion of conjugation degree, and the research on the carrier transmission process and mechanism is very necessary. As an emerging field of research, there have been few reports of the fusion of azulenes into conjugated molecules to date. Whereas the fusion of azulene rings to extended backbone perylene imide (PDI) systems has never been reported.
Disclosure of Invention
One of the purposes of the invention is to develop a conjugated molecular material fused with perylene diimide and non-benzene azulene rings, develop a preparation method of the material, synthesize a series of derivatives with various structures, and research the application of the derivatives as materials of organic field effect transistors, chiral optics and the like.
The perylene diimide and azulene condensed compounds provided by the invention comprise eight classes, and have the structural formula as shown in formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The following is shown:
the above formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 Wherein R is 1 Can independently be H, a C6-C18 linear alkyl group (which can be specifically (-C) 6 H 13 ))、C6-C3Branched alkyl of 9 (which may specifically be- (CH) 2 )CH(C 8 H 17 )(C 10 H 21 ) Any one of a substituted or unsubstituted phenyl group;
wherein the substituent in the substituted phenyl can be selected from at least one of H, C1-C6 branched or branched alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine and iodine, and can be specifically 2, 6-diisopropyl;
the formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 Wherein R is 2 Can be independently selected from H, C C18 straight or branched alkyl groups (which can be specifically (-C (CH) 3 ) 3 ) Any one of, F, cl, br, I and cyano.
The above formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The compounds shown may be specifically:
the above formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The perylene diimide compound shown is prepared by a method comprising the steps of:
1) From II 1 ，Ⅱ 2 ，Ⅱ 3 The compound shown in the formula II 4 ，Ⅱ 5 ，Ⅱ 6 And II 7 The compounds respectively undergo coupling reaction under the catalysis of tetraphenylphosphine palladium to obtain the formula III 1 -III 8 A compound shown in the specification;
above II 1 II 2 II 3 Wherein R is 1 Can independently be H, a C6-C18 linear alkyl group (which can be specifically (-C) 6 H 13 ) Branched alkyl of C6-C39 (which may be specifically- (CH) 2 )CH(C 8 H 17 )(C 10 H 21 ) Any one of a substituted or unsubstituted phenyl group;
wherein the substituent in the substituted phenyl can be selected from at least one of H, C1-C6 branched or branched alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine and iodine, and can be specifically 2, 6-diisopropyl;
above II 4 ，Ⅱ 5 ，Ⅱ 6 And II 7 Wherein R is 2 Can be independently selected from H, C C18 straight or branched alkyl groups (which can be specifically (-C (CH) 3 ) 3 ) Any one of F, cl, br, I and cyano;
III 1 -Ⅲ 8 Wherein R is 1 Can independently be H, a C6-C18 linear alkyl group (which can be specifically (-C) 6 H 13 ) Branched alkyl of C6-C39 (which may be specifically- (CH) 2 )CH(C 8 H 17 )(C 10 H 21 ) Any one of a substituted or unsubstituted phenyl group;
wherein the substituent in the substituted phenyl can be selected from at least one of H, C1-C6 branched or branched alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine and iodine, and can be specifically 2, 6-diisopropyl;
R 2 can be independently selected from H, C C18 straight or branched alkyl groups (which can be specifically (-C (CH) 3 ) 3 ) Any one of F, cl, br, I and cyano;
2) Under the illumination condition, lead to the formula III 1 -III 8 Cyclizing the compound to obtain the compound shown in formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The compounds shown.
In the above method step 1), formula II 1 II is a kind of 4 II is a kind of 5 II is a kind of 6 And II 7 Are all synthesized by known literature methods (Chem.Commun., 2015,51,12585;J.Org.Chem.2018,83,1298-1303); II type 2 And II 3 The compounds shown are mixtures obtained directly from the reagents company in a ratio of approximately 3:1, separating by HPLC to obtain two pure compounds;
II type 1 、Ⅱ 2 Or II 3 The compound shown in the formula II 4 、Ⅱ 5 、Ⅱ 6 Or II 7 The molar ratio of the compound to the triphenylphosphine palladium can be as follows: 1:2.1-5.0:0.02-0.5; specifically, the ratio of the raw materials can be 1:2.5:0.1
The temperature of the coupling reaction can be 90-120 ℃, and can be specifically 110 ℃; the time can be 6-48h, and can be specifically 12h;
the reaction is carried out under nitrogen atmosphere;
the coupling reaction is carried out in an organic solvent, and the organic solvent can be toluene and tetrahydrofuran;
step 1) further comprises the operation of separation and purification: spin-drying the solvent in the system after the coupling reaction, and separating by column chromatography with petroleum ether/dichloromethane (3:1-1:1, volume ratio) as eluent to obtain formula III respectively 1 III 2 III 3 III 4 III 5 III 6 III 7 And III 8 Dissolving the compound in chloroform solvent, slowly adding methanol until solid is separated out, standing for a period of time, filtering to obtain solid, and washing with methanol to obtain formula III 1 III 2 III 3 III 4 III 5 III 6 III 7 And III 8 A compound shown in the specification;
in the step 2), the light source may be one of ultraviolet light, visible light and blue light, and may specifically be a blue light LED;
in step 2), a photosensitizer is added, which may be specifically I 2 The method comprises the steps of carrying out a first treatment on the surface of the The photosensitizer can be added in an amount of 0.2-20 equivalents;
the illumination time can be 48-100h, and can be specifically 72h;
the temperature of the reaction can be 25-90 ℃, and can be 85 ℃;
the cyclization reaction is carried out in a solvent, wherein the solvent can be toluene and methylene dichloride, and can be toluene in particular;
the reaction is carried out under an air atmosphere;
step 2) further comprises the operation of separation and purification: spin-drying the system after cyclization reaction, firstly using petroleum ether as an eluent to remove superfluous photosensitizer of the system, and then using petroleum ether/dichloromethane (3:1-0:1, volume ratio) and dichloromethane/methanol (0:1-10:1, volume ratio) as eluent to obtain I 1 -I 8 The compound is further recrystallized to obtain I with higher purity 1 -I 8 A compound shown in the specification;
another object of the present invention is to provide the above formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The use of the compounds shown as p-type semiconductor materials.
The application may be specifically of formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The application of the compound in preparing field effect device,
the field effect transistor device exhibits p-type charge transport properties.
The invention also provides a field effect device and a preparation method thereof.
The field effect device provided by the invention adopts the I 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 The compounds shown are p-type semiconductor materials.
The field effect device is prepared by a method comprising the following steps:
by reacting the above formula I 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 Evaporating the compound onto a substrate to manufacture the field effect device;
in the preparation method, the thickness of the vapor deposition film can be 15nm, the vapor deposition rate can be 0.02-0.05 angstrom/s, and the substrate temperature is 20 ℃;
the preparation and the test of the field effect device are carried out in a nitrogen atmosphere;
the substrate is a common substrate known in the art, the electrode is a gold electrode, and the electrode is directly used after ultraviolet ozone treatment and Octadecyl Trichlorosilane (OTS) modification and cleaning are finished.
It is yet another object of the present invention to provide small molecule materials with near infrared absorption.
The material may be specifically represented by the formula I 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 Materials made of the indicated compounds;
the test method provided by the invention comprises the following steps of 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 The compound is dissolved in chloroform solution with the concentration of 10 -5 mol/L；
The small molecule I 1 And I 3 The maximum absorption wavelengths of (a) are respectively: 793nm and 807nm.
The invention has the following advantages:
the invention develops a condensed molecular skeleton of the non-benzene azulene ring and the perylene imide for the first time; provided formula I 1 -I 8 The compound has excellent hole transport property and dissolution property, and is beneficial to researching the semiconductor property; they all exhibit near infrared absorption characteristics and have a large molar extinction coefficient, making the compounds potentially useful in photothermal applications.
Drawings
FIG. 1 shows the formula I of the present invention 1 And I 3 A process for the preparation of the compounds shown.
FIG. 2 is a diagram of formula I in example 1 of the present invention 1 The crystal structure of the compound.
FIG. 3 is a block diagram of formula I prepared in example 1 of the present invention 1 And I 3 Ultraviolet-visible absorption spectra of chloroform solutions of the compounds shown.
FIG. 4 is a block diagram of formula I prepared in example 1 of the present invention 1 And I 3 Cyclic voltammograms of the compounds shown.
Detailed Description
The present invention will be described with reference to the following specific examples, but the present invention is not limited thereto.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; the reagents, materials, etc. used in the examples described below are commercially available unless otherwise specified.
The perylene diimide and azulene condensed compounds provided by the invention comprise eight classes, and have the structural formula as shown in formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The following is shown:
the above formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 Wherein R is 1 Can independently be H, a C6-C18 linear alkyl group (which can be specifically (-C) 6 H 13 ) Branched alkyl of C6-C39 (which may be specifically- (CH) 2 )CH(C 8 H 17 )(C 10 H 21 ) Any one of a substituted or unsubstituted phenyl group;
wherein the substituent in the substituted phenyl can be selected from at least one of H, C1-C6 branched or branched alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine and iodine, and can be specifically 2, 6-diisopropyl;
the formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 Wherein R is 2 Can be independently selected from H, C C18 straight or branched alkyl groups (which can be specifically (-C (CH) 3 ) 3 ) Any one of, F, cl, br, I and cyano.
The invention also provides a compound of formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The use of the compounds shown as p-type semiconductor materials.
The application may be specifically of formula I 1 ，I 2 ，I 3 ，I 4 ，I 5 ，I 6 ，I 7 And I 8 The application of the compound in preparing field effect device,
the field effect transistor device exhibits p-type charge transport properties.
The invention also provides a field effect device and a preparation method thereof.
The field effect device provided by the invention adopts the I 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 The compounds shown are p-type semiconductor materials.
It is yet another object of the present invention to provide small molecule materials with near infrared absorption.
The material may be specifically represented by the formula I 1 、I 2 、I 3 、I 4 、I 5 、I 6 、I 7 Or I 8 Materials made from the compounds shown.
The invention develops a condensed molecular skeleton of the non-benzene azulene ring and the perylene imide for the first time; provided formula I 1 -I 8 The compound has excellent hole transport property and dissolution property, and is beneficial to researching the semiconductor property; they all exhibit near infrared absorption characteristics and have a large molar extinction coefficient, making the compounds potentially useful in photothermal applications.
Compounds 2 and 3 of the following examples (i.e., formula II 2 And II 3 ) Is a commercially available mixture, in a ratio of about 3:1, available from zheng state alpha chemical company.
Example 1, formula I 1 And I 3 Synthesis of the Compound (in the formula I, R 1 Is n-hexyl, R 2 Is tert-butyl; i is a kind of 3 Wherein R is 1 Is octyl dodecyl, R 2 Hydrogen atom):
the chemical reaction flow chart is shown in fig. 1, and the specific reaction step conditions are as follows:
i is a kind of 1 The synthesis steps of the compounds shown:
to a 50mL round bottom flask equipped with a magneton was added Compound 1 (200 mg,0.28 mmol), 4 (182 mg,0.7 mmol), sodium carbonate (222 mg,2.1 mmol) and Pd (PPh) 3 ) 4 (16 mg,0.014 mmol). The mixture was degassed and purged with nitrogen three times. Toluene (15 mL), ethanol (5 mL) and water (5 mL) were then added to the flask. The mixture was heated at 110℃for 12 hours. After cooling to room temperature, the reaction was quenched with water (10 mL) and the mixture was extracted with dichloromethane (30 ml×3). The organic layer is treated by Na 2 SO 4 Dried and concentrated under reduced pressure. The crude product was then purified by flash column chromatography using petroleum ether (60-90 ℃)/dichloromethane=2/1 as eluent to give purple solid 6 (161 mg, 71% yield).
The structure validation data are as follows:
1 H NMR(400MHz,CDCl 3 )δ(ppm):8.63(d,J＝12Hz,2H),8.14(d,J＝12Hz,4H),7.98(s,2H),7.90(d,J＝8.0Hz,2H),7.35(s,4H),7.34-7.32(d,J＝8.0Hz,4H),3.58(t,J＝8.0Hz,4H),1.62(m,4H),1.47(s,18H),1.27(s,12H),0.85(t,J＝8.0Hz,6H)； 13 C NMR(100MHz,CDCl 3 ):δ168.6,167.6,161.1,149.6,140.1,138.1,136.6,135.7,134.5,133.4,129.7,128.9,127.3,124.6,124.2,121.9,121.5,115.6,38.2,37.5,31.4,30.9,28.1,26.1,22.0,13.5；
HR-MS: calculated value C 64 H 62 N 2 O 4 (M + ): 922.4710, experimental test values are: 922.4714;
from the above, the structure of the product was correct.
To a quartz tube containing a magneton, compound 6 (15 mg. Times.2, 0.037 mmol), iodine (20 mg. Times.2, 0.15 mmol) and toluene (10 mL. Times.2) were added. The mixture was illuminated with blue LED at 85 ℃ for 72 hours. After cooling to room temperature, the residue obtained was filtered as crude product. The crude product was then purified by column chromatography using dichloromethane/methanol=20/1 as eluent to give 7 (10 mg) as a brown solid in 23.5% yield.
The structure validation data are as follows:
1 H NMR(500MHz,CDCl 2 CDCl 2 )δ(ppm):9.74(d,J＝5.0Hz,2H),8.96(d,J＝5.0Hz,2H),8.74(d,J＝10.0Hz,2H),8.66(d,J＝10.0Hz,2H),8.08(s,2H),7.77(d,J＝10.0Hz,2H),7.58(d,J＝10.0Hz,2H),3.96(t,J＝10.0,4H),1.97-2.02(m,4H),1.66(s,18H),1.46-1.57(m,12H),1.01(t,J＝5.0,6H)； 13 C NMR(125MHz,CDCl 2 CDCl 2 ):δ168.3,167.8,159.7,139.4,138.1,137.8,135.7,134.9,124.6,124.3,123.5,123.2,123.0,122.5,122.2,121.0,121.0,120.4,119.3,119.2,116.1,110.3,37.3,36.9,30.4,30.3,27.5,25.3,21.1,12.6；
HR-MS: calculated value C 64 H 58 N 2 O 4 (M - ): 918.4397, experimental test values are: 918.4400;
from the above, the structure of the product was correct.
I is a kind of 3 The synthetic route for the compounds shown:
into a 100mL round bottom flask equipped with a magneton was added compound 2 (300 mg,0.27 mmol), 5 (206 mg,0.81 mmol), sodium carbonate (214 mg,2 mmol) and Pd (PPh) 3 ) 4 (31 mg,0.027 mmol). The mixture was degassed and purged with nitrogen three times. Toluene (20 mL), ethanol (8 mL) and water (8 mL) were then added to the flask. The mixture was heated at 110℃for 12 hours. After cooling to room temperature, the reaction was quenched with water (10 mL) and the mixture was extracted with dichloromethane (30 ml×3). The organic layer is treated by Na 2 SO 4 Dried and concentrated under reduced pressure. The crude product was then purified by flash column chromatography using petroleum ether (60-90 ℃)/dichloromethaneAlkane=2/1 as eluent, yielding solids 8 (90 mg, yield 27.7%) and 9 (188 mg, yield 57.9%).
The structure validation data are as follows:
compound 8
1 H NMR(400MHz,CDCl 3 )δ(ppm):8.72(s,2H),8.26(d,J＝12.0Hz,4H),8.99(d,J＝8.0Hz,2H),7.87(d,J＝8.0Hz,2H),7.61(t,J＝8.0Hz,2H),7.50(s,4H),7.58(d,J＝10.0Hz,2H),7.21(t,J＝8.0Hz,2H),4.12(d J＝8.0,4H),1.96-2.00(m,2H),1.12-1.41(m,64H),0.80-0.85(m,12H)； 13 C NMR(100MHz,CDCl 3 ):δ162.8,149.4,140.8,136.9,136.4,136.0,135.2,133.7,131.8,128.9,128.3,128.0,126.5,123.2,121.2,121.0,115.3,43.7,35.6,30.9,30.7,29.0,28.6,28.6,28.6,28.3,28.3,25.5,21.6,13.1；
HR-MS: calculated value C 84 H 102 N 2 O 4 (M - ): 1202.7840, experimental test values are: 1202.7848;
from the above, the structure of the product was correct.
Compound 9
1 H NMR(400MHz,CDCl 3 )δ(ppm):9.52(s,1H),9.00(s,1H),8.99(d,J＝8.0Hz,1H),8.67(s,1H),8.37(d,J＝12.0Hz,2H),8.31(d,J＝12.0Hz,1H),8.23(d,J＝8.0Hz,1H),8.09(d,J＝8.0Hz,1H),7.70(d,J＝8.0Hz,2H),7.66(d,J＝4.0Hz,1H),7.51(s,2H),7.26-7.43(m,4H),4.10(d,J＝8.0,2H),4.22(d,J＝8.0,2H),1.98(m,1H),2.08(m,1H),1.15-1.44(m,64H),0.76-0.84(m,12H)； 13 C NMR(100MHz,CDCl 3 ):δ164.1,163.7,163.7,163.6,152.1,141.9,141.4,140.9,138.0,137.7,137.3,132.8,130.4,127.1,126.0,125.5,124.2,123.9,123.4,122.0,121.9,121.0,120.7,120.5,116.1,45.1,44.7,37.0,36.9,31.9,31.9,31.9,30.2,30.2,29.8,29.7,29.7,29.7,29.7,29.4,29.3,26.7,26.6,22.7,22.7,22.6；
HR-MS: calculated value C 84 H 100 N 2 O 4 (M - ): 1200.7683, experimental test values are: 1200.7679;
from the above, the structure of the product was correct.
To a quartz tube containing a magneton were added compound 8, compound 9 (70 mg. Times.2, 0.11 mmol), iodine (80 mg. Times.2, 0.63 mmol) and toluene (15 mL. Times.2), propylene oxide (1 mL. Times.2). The mixture was illuminated with blue LEDs for 20 hours at 85 ℃. After cooling to room temperature, the solvent was dried by spin-drying. The crude product was then purified by column chromatography using petroleum ether/dichloromethane=1/1 as eluent to give 10 (91 mg) as a reddish brown solid in 65% yield.
The structure validation data are as follows:
1 H NMR(400MHz,CDCl 3 )δ(ppm):10.10(s,2H),9.60(s,2H),9.57(d,J＝10.0Hz,2H),8.65(d,J＝10.0Hz,2H),8.25(s,2H),7.93(t,J＝10.0Hz,2H),7.78(t,J＝10.0Hz,2H),7.54(t,J＝10.0Hz,2H),4.24(d,J＝5.0Hz,4H),2.14-2.17(m,2H),1.13-1.30(m,64H),0.74-0.81(m,12H)；
HR-MS: calculated value C 84 H 98 N 2 O 4 (M - ): 1198.7527, experimental test values are: 1198.7522;
from the above, the structure of the product was correct.
Example 2, formula I 1 The crystal structure and packing of the indicated compounds:
preparation of crystals: i prepared in example 1 1 The compound (R2 is tertiary butyl) is dissolved in toluene solution, and methanol is slowly diffused into the toluene solution by a diffusion method to obtain the compound.
The crystal structure and stacking of the compounds of the present invention are shown in FIG. 2, and the compounds have saddle-shape in the crystal, exhibit large torsion angles, and exhibit helical chirality. Exhibits weaker pi-pi interactions between molecules, with pi-pi distances of
Example 3, formula I 1 And I 3 Ultraviolet-visible absorption spectrum of the compound in chloroform solution:
the compound (I) produced in example 1 of the present invention 1 And I 3 Visualization ofCompound) in a variety of organic solvents including chloroform, o-dichlorobenzene, 1, 2-tetrachloroethane, and other solvents such as: toluene, tetrahydrofuran, and the like. The compounds of the present invention have good solubility in chlorinated solvents. By reacting the formula I 1 And I 3 The absorption spectrum of the solution obtained by dissolving the compound in chloroform solution is shown in FIG. 3. As can be seen from FIG. 3, the compounds 7 and 10 each have a longest absorption wavelength of 793nm and 807nm, respectively, and exhibit good near infrared absorption characteristics.
Example 4 front orbital levels (HOMO and LUMO levels) were measured using cyclic voltammetry:
the electrochemical workstation was used to perform the process of the present invention according to formula I prepared in example 1 1 And I 3 The electrochemical characteristics of the compounds were tested using a three electrode test system, with a glassy carbon electrode as the working electrode, an Ag/AgCl electrode as the reference electrode, and a platinum wire electrode as the counter electrode. The cyclic voltammogram of ultra-dry methylene chloride solutions of 7 and 10 were tested using tetrabutylammonium hexafluorophosphate as a supporting electrolyte (0.1 mol/L) and ferrocene as an internal standard at a scan rate of 100mV/s, as shown in FIG. 4. As can be seen from FIG. 4, the HOMO and LUMO levels of Compound 7 were-4.83V and-3.58V, respectively, and the HOMO and LUMO levels of Compound 10 were-5.13V and-3.72V, respectively.
Example 5 preparation of field effect device:
according to the method of literature (chem. Rev.2012,112, 2208-2267), a layer of 300nm thick silicon dioxide is plated on monocrystalline silicon, which is then gold-plated by means of photolithography, with a width of 1440 microns and a length of 50 microns, the surface is treated with uv ozone first and then modified with a monolayer of octadecyltrichlorosilane.
The compound 7 produced in example 1 of the present invention was vapor-deposited on the above-mentioned modified sheet. Preparing a field effect device of the obtained compound by setting the temperature of a substrate in evaporation to 20 ℃ and testing the field effect property of the field effect device;
the compound 10 produced in example 1 of the present invention was prepared in a chloroform solution of 5mg/mL and spun onto the above-mentioned modified sheet by spin coating. The rotation speed is 2500r/min, and the film throwing time is 50s. Annealing the film-thrown film at 80 ℃,120 ℃,160 ℃ and 180 ℃ for 10min respectively to prepare a field effect device of the compound, and testing the field effect property of the field effect device;
both compounds showed p-type semiconductor properties under nitrogen atmosphere, with a large on-off ratio, and mobility of compound 10 reached 4×10 after annealing -3 cm 2 V -1 s -1 . Compound 7 has a slightly lower mobility than compound 10, up to 10 -4 cm 2 V -1 s -1 . May be associated with compound 7 exhibiting a more pronounced distortion, being less planar than compound 10, and having weaker intermolecular interactions. The result shows that the invention realizes the synthesis of non-benzene conjugated condensed rings of different perylene diimides by changing the structure of perylene diimides and the position isomerism of azulenes, and the regulation and control effect of the compound structure on the performance is illustrated by comparing the photophysical and electrical properties of the perylene diimides.
Claims (5)
1. Perylene diimide and azulene fused compound with structural formula as I 1 Or I 3 The following is shown:
2. formula I in claim 1 1 Or I 3 The use of the compounds shown as p-type semiconductor materials.
3. The use according to claim 2, characterized in that: the application is of formula I 1 Or I 3 The use of the compounds shown for the preparation of field effect devices which exhibit p-type charge transport properties.
4. A field effect device of formula I in claim 1 1 Or I 3 The compounds shown are p-type semiconductor materials.
5. With near infrared absorptionIs a small molecule material of the formula I as claimed in claim 1 1 Or I 3 Materials made from the compounds shown.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110381085.2A CN115197219B (en) | 2021-04-09 | 2021-04-09 | Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110381085.2A CN115197219B (en) | 2021-04-09 | 2021-04-09 | Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115197219A CN115197219A (en) | 2022-10-18 |
| CN115197219B true CN115197219B (en) | 2023-11-07 |
Family
ID=83570574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110381085.2A Active CN115197219B (en) | 2021-04-09 | 2021-04-09 | Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115197219B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05179237A (en) * | 1991-12-26 | 1993-07-20 | Konica Corp | Organic thin-film electroluminescent element |
| WO2009021663A1 (en) * | 2007-08-10 | 2009-02-19 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Doped semiconductor material and use thereof |
| CN104028308A (en) * | 2014-06-20 | 2014-09-10 | 中国科学院新疆理化技术研究所 | Nanometer photo-catalyst used in producing hydrogen by decomposing water under visible light response and application of nanometer photo-catalyst |
-
2021
- 2021-04-09 CN CN202110381085.2A patent/CN115197219B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05179237A (en) * | 1991-12-26 | 1993-07-20 | Konica Corp | Organic thin-film electroluminescent element |
| WO2009021663A1 (en) * | 2007-08-10 | 2009-02-19 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Doped semiconductor material and use thereof |
| CN104028308A (en) * | 2014-06-20 | 2014-09-10 | 中国科学院新疆理化技术研究所 | Nanometer photo-catalyst used in producing hydrogen by decomposing water under visible light response and application of nanometer photo-catalyst |
Non-Patent Citations (1)
| Title |
|---|
| Motoki Yoshida等.《J. Phys. Chem. C》/Inter- and Intramolecular Electron-Transfer Reduction Properties of Coronenediimide Derivatives via Photoinduced Processes.2017,第122卷(第25期),全文. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115197219A (en) | 2022-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108546267B (en) | Organic conjugated micromolecule material with terminal group containing cycloalkyl chain, preparation method thereof and application thereof in solar cell | |
| Zhou et al. | High efficiency small molecular acceptors based on novel O-functionalized ladder-type dipyran building block | |
| CN109593095B (en) | X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof | |
| CN111171291B (en) | Benzodithiophenedione-benzodithiophene type double-cable polymer and preparation and application thereof | |
| CN106349252B (en) | Compound based on fused indacenodithiophene and application thereof | |
| Chen et al. | Effect of aromatic π-bridges on molecular structures and optoelectronic properties of A-π-D-π-A small molecular acceptors based on indacenodithiophene | |
| CN113292583B (en) | Diphenylamino-truxene-BODIPY derivative ternary system organic dye and preparation method and application thereof | |
| CN115197219B (en) | Non-benzene perylene diimide conjugated fused ring molecule, and preparation method and application thereof | |
| CN114133385B (en) | Hole transport material with carbazole as core and thiophene or phenoxazine as end group, and synthesis method and application thereof | |
| CN113292585B (en) | BODIPY-benzothiadiazole-porphyrin-carbazole quaternary system linear compound and preparation method thereof | |
| CN113444117B (en) | Star-shaped compound of BODIPY bridged tetraperylene diimide derivative and preparation method thereof | |
| CN105294721A (en) | Synthetic method and micrometer wire preparation method of perylene bisimide derivative | |
| CN115197260A (en) | Alkynyl coupled double-BODIPY near-infrared fluorescent dye with J aggregation effect and preparation method thereof | |
| CN111892605B (en) | Novel five-membered ring perylene diimide molecular material, and preparation method and application thereof | |
| CN109897055B (en) | Organic compound based on bi-carbazole and perylene diimide and preparation method and application thereof | |
| CN109134477B (en) | Aza-tetracene analogue of pyrrole mono-ketone, preparation method and application thereof | |
| CN110016037B (en) | Novel aza-condensed ring compound and preparation method and application thereof | |
| CN113201022A (en) | Small conjugated phosphorescent metal iridium (III) complex with isomer and preparation method and application thereof | |
| JP7062284B2 (en) | A novel porphyrin derivative, a method for producing a porphyrin derivative, a donor material, a photoelectric conversion device, and a method for manufacturing a photoelectric conversion device. | |
| CN110698486A (en) | Hexaazatriphenylene triaminoquinone derivative and synthesis method thereof | |
| CN111747894A (en) | Compound with dibenzo-nitrogen-containing six-membered heterocyclic ring as core and application of compound in organic electroluminescent device | |
| KR101728738B1 (en) | organic semiconductor compounds, its manufacturing method and organic semiconductor device using the same | |
| JP3712037B2 (en) | Cyclic compounds and organic electroluminescent materials | |
| CN114181242B (en) | Silane-substituted aromatic fused ring compound and preparation method and application thereof | |
| Alidagi et al. | A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties |
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 |