CN111574538A - D-A type near-infrared organic luminescent material and preparation method and application thereof - Google Patents
D-A type near-infrared organic luminescent material and preparation method and application thereof Download PDFInfo
- Publication number
- CN111574538A CN111574538A CN202010546566.XA CN202010546566A CN111574538A CN 111574538 A CN111574538 A CN 111574538A CN 202010546566 A CN202010546566 A CN 202010546566A CN 111574538 A CN111574538 A CN 111574538A
- Authority
- CN
- China
- Prior art keywords
- reaction
- luminescent material
- organic luminescent
- type near
- infrared
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229960000583 acetic acid Drugs 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 14
- 239000012362 glacial acetic acid Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- UXSHNPXCELYWAW-UHFFFAOYSA-N 5,6-dibromo-1,2-dihydroacenaphthylene Chemical compound C1CC2=CC=C(Br)C3=C2C1=CC=C3Br UXSHNPXCELYWAW-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 229940117975 chromium trioxide Drugs 0.000 claims description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 8
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- DTCXDDLFSKSMSG-UHFFFAOYSA-A tetrabutylazanium hexaphosphate Chemical group P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC DTCXDDLFSKSMSG-UHFFFAOYSA-A 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000006683 Mannich reaction Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 4
- -1 naphthothiazole quinoxaline Chemical compound 0.000 abstract description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000543 intermediate Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000003480 eluent Substances 0.000 description 16
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000002243 precursor Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
- 238000000295 emission spectrum Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ICBFWYCPTDMCRB-UHFFFAOYSA-N 5,6-dimethyl-[1,2,5]thiadiazolo[3,4-b]pyrazine Chemical compound N1=C(C)C(C)=NC2=NSN=C21 ICBFWYCPTDMCRB-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical group [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- NIBRHTKNFWGZFF-UHFFFAOYSA-N quinoxaline;1,3-thiazole Chemical compound C1=CSC=N1.N1=CC=NC2=CC=CC=C21 NIBRHTKNFWGZFF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- DTDZVQXOCHUQLZ-UHFFFAOYSA-N thiadiazolo[5,4-f]quinoxaline Chemical compound C1=CC2=NC=CN=C2C2=C1N=NS2 DTDZVQXOCHUQLZ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01S—DEVICES USING THE PROCESS OF LIGHT AMPLIFICATION BY STIMULATED EMISSION OF RADIATION [LASER] TO AMPLIFY OR GENERATE LIGHT; DEVICES USING STIMULATED EMISSION OF ELECTROMAGNETIC RADIATION IN WAVE RANGES OTHER THAN OPTICAL
- H01S5/00—Semiconductor lasers
- H01S5/30—Structure or shape of the active region; Materials used for the active region
- H01S5/36—Structure or shape of the active region; Materials used for the active region comprising organic materials
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1081—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with sulfur
Abstract
The invention relates to a D-A type near-infrared organic luminescent material, a preparation method and application thereof, in particular to a naphthothiazole quinoxaline introduced as a rigid large-plane electron acceptor structure in a closed-loop mode. A strong electron donor structure with a high HOMO energy level is selected, and intermolecular torque is enhanced through the change of the connection position, so that the separation of HOMO/LUMO energy levels is effectively enhanced. The invention provides a series of D-A type near-infrared organic light-emitting materials containing naphthothiazole quinoxaline structural units. The invention has the advantages of easily obtained raw materials, simple preparation process, easily controlled reaction process, easily separated product, high yield and high purity; the material has good thermal stability, and the film state luminescence is in a near infrared region; the organic electroluminescent material has important application potential in the aspect of near infrared organic electroluminescent devices.
Description
Technical Field
The invention belongs to the field of photoelectric materials and technologies, and particularly relates to a D-A type near-infrared organic luminescent material, and a preparation method and application thereof.
Background
However, Near-infrared Organic Light emitting diodes (NIR OLEDs) generally have the problems of relatively poor Organic Light source, limited wavelength, low efficiency and the like, so that the device performance of the OLED is far behind that of an OLED in a visible Light bandEQEOver 24%. Although the efficiency of these phosphorescent NIR OLEDs is very high, the high cost and resource shortages of noble metals such as platinum and iridium greatly limit their potential for practical applications. Therefore, it is crucial to develop efficient metal-free NIR OLEDs.
Thermally Activated Delayed Fluorescence (TADF) simultaneously collects singlet and triplet excitons in an efficient reverse intersystem crossing (RISC) process, and thus can achieve a theoretical 100% Internal Quantum Efficiency (IQE). Due to the adoption of the form of intermolecular exciplex formed by the electron donor and the electron acceptor or the combination of the electron donor and the electron acceptor with high density in molecules, the overlapping of HOMO and LUMO molecular rails is reduced, and high-efficiency delayed fluorescence emission is realized. Currently, the External Quantum Efficiency (EQE) of blue, green, and red TADFOLEDs is as high as 37.5%, 31.3%, and 17.5%, respectively. In contrast, NIR TADF OLEDs still have to be improved in terms of device efficiency and color purity since the emission wavelength is inversely related to the emission efficiency of the near-infrared fluorophore.
Disclosure of Invention
The technical problem is as follows: the invention aims to provide a D-A type near-infrared organic luminescent material, a preparation method and application thereof, so as to solve the problems of the shortage of near-infrared materials, the low device efficiency of electroluminescent devices and the like.
The technical scheme is as follows: the invention discloses a D-A type near-infrared organic luminescent material, a preparation method and application thereof.
The preparation method of the near-infrared organic luminescent material comprises the following steps:
the method comprises the following steps: under the conditions of light protection and nitrogen protection, the monomer 4, 5-dinitro-1, 2-aminobenzene is dissolved in toluene and thionyl chloride, and the reaction is carried out for 36 hours at 70-110 ℃. Removing all solvents, adding iron powder and acetic acid into the reaction flask under the condition of keeping out of the light, and reacting for 4 hours at the temperature of 60-80 ℃. After the reaction is finished, ethyl acetate and methanol are used as eluent to obtain an intermediate 1 through silica gel column purification;
the molar ratio of the iron powder to the 4, 5-dinitro-1, 2-amino is 8: 1-16: 1. Adding 3-6L of thionyl chloride into each mole of 4, 5-dinitro-1, 2-amino, wherein the volume ratio of toluene to thionyl chloride is 1: 1;
step two: 5, 6-dibromo acenaphthene and chromium trioxide are dissolved in acetic anhydride and react for 2 hours at 70-110 ℃. After the reaction is finished, cooling to room temperature, and adding H2O, followed by the slow addition of concentrated hydrochloric acid and stirring at room temperature for 2-6 hours. Pouring into water, carrying out suction filtration and drying to obtain an intermediate 2;
in the second step, the molar ratio of each mole of chromium trioxide to 5, 6-dibromoacenaphthene is 6: 1-12: 1, and 4-6L of acetic anhydride is added into each mole of 5, 6-dibromoacenaphthene;
step three: adding an electron donor with borate group (the electron donor with borate group is provided with borate group before reaction, and the borate group can be removed as impurity after reaction), adding the intermediate 2 and phase transfer catalyst tetrabutyl ammonium hexaphosphate into 2M K2CO3And toluene, and reacting at 75-105 deg.c for 24-48 hr. After the reaction is finished, cooling to room temperature, and adding H2Quenching O, extracting with dichloromethane, removing the solvent from the organic phase, and purifying the obtained solid with ethyl acetate and dichloromethane as eluent through a silica gel column to obtain an intermediate 3;
said borate group-bearingThe molar ratio of the electron donor to the intermediate 2 is 2: 1-6: 1, 30L of toluene solvent is added into each mole of the intermediate 2, and the toluene and the K are mixed2CO3The volume ratio of the aqueous solution is 3: 1;
step four: in the absence of light and N2Under the protection condition, dissolving the intermediate 1 synthesized in the step one and the intermediate 3 synthesized in the step three in a glacial acetic acid and chloroform solution, and reacting for 4-8 hours at 60-80 ℃. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into water. Filtering off the separated solid, washing with water and cold methanol, and purifying the obtained solid by using dichloromethane and ethyl acetate as eluent through a silica gel column to obtain the D-A type TADF material;
the molar ratio of the intermediate 1 to the intermediate 3 is 1: 1-1.5: 1, 20L of glacial acetic acid is added into each mole of the intermediate 3, and the volume ratio of chloroform to glacial acetic acid is 3: 1.
Wherein Ar is a strong electron donor and is one of the following structures:
the invention also aims to provide the D-A type near-infrared organic luminescent material prepared by the method.
The D-A type near-infrared organic luminescent material can be used as an active layer material to be applied to the organic photoelectric field such as organic electroluminescent devices, organic field effect transistors or organic laser gain media.
Has the advantages that: the TADF organic luminescent material with the D-A structure can realize luminescence in red and near-infrared bands, is applied to an organic electroluminescent device, and can effectively improve the luminous efficiency of the near-infrared luminescent device, thereby showing excellent device performance; the material can be used as a stable and efficient laser gain medium material with low threshold and high gain, and is applied to organic laser.
Drawings
FIG. 1 shows IR-11H NMR spectrum;
FIG. 2 is a MALDI-TOF spectrum of IR-1;
FIG. 3 shows IR-21H NMR spectrum;
FIG. 4 is a MALDI-TOF spectrum of IR-2;
FIG. 5 shows IR-31H NMR spectrum;
FIG. 6 is a MALDI-TOF spectrum of IR-3;
FIG. 7 shows IR-41H NMR spectrum;
FIG. 8 is a MALDI-TOF spectrum of IR-4;
FIG. 9 shows IR-51H NMR spectrum;
FIG. 10 is a MALDI-TOF spectrum of IR-5;
FIG. 11 is the absorption spectrum of target molecule IR-1 in solution and thin film;
FIG. 12 shows fluorescence spectra of target molecule IR-1 in solution and thin film;
FIG. 13 is an absorption spectrum of the target molecule IR-1-5 in a solution state;
FIG. 14 is an emission spectrum of the target molecule IR-1 in a solution state;
FIG. 15 is a thermogravimetric analysis spectrum of the target molecule IR-1;
FIG. 16 is a graph showing a simulated energy level distribution of the target molecule IR-1.
Detailed Description
The synthesis method comprises the following steps: a rigid large planar electron acceptor structure is prepared by a closed-loop method, and the electron acceptor has thiazole quinoxaline (thiadiazole quinoxaline [1,2,5] thiadiazolo [3,4-g ] quinoxaline, abbreviated as thiadiazolo Quinoxaline (QTD), effective Non-bonded Near Organic Light-Emitting devices based on fluorine with Aggregation-Induced emission enhancement, xiaoo Du et, Chemistry of Materials, 2012,24, 2178-. Simultaneously selecting different strong electron donors Ar with high HOMO energy levels, and preparing a target compound through Suzuki coupling to form the near-infrared TADF organic luminescent material which takes the naphthothiazole quinoxaline as a rigid large plane electron acceptor and takes a strong electron group as an electron donor and has a D-A structure, wherein the material has a general structural formula shown in the following formula I:
wherein Ar in the formula I is a strong electron donor and is one of the following structures:
wherein, is the connection position; n is a nitrogen atom; s is a sulfur atom; o is an oxygen atom; me is methyl.
The preparation method of the near-infrared organic luminescent material comprises the following steps:
the method comprises the following steps: i 1mmol of the monomer 4, 5-dinitro-1, 2-aminobenzene is dissolved in 3-6mL of toluene and 3-6mL of thionyl chloride under protection of light and nitrogen, and reacted at 70-110 ℃ for 12-36 hours. Ii, removing all solvents, adding 8-16mmol of iron powder and 3-6L of acetic acid into the reaction flask under the condition of keeping out of the light, and reacting for 4-8 hours at the temperature of 60-80 ℃. After the reaction is finished, ethyl acetate and methanol are used as eluent to obtain an intermediate 1 through silica gel column purification;
step two: iii dissolving 1mmol of 5, 6-dibromoacenaphthene and 6-12mmol of chromium trioxide in 4-6mL of acetic anhydride, and reacting at 70-110 ℃ for 2 hours. After the reaction is finished, cooling to room temperature, and adding H2O, followed by the slow addition of concentrated hydrochloric acid and stirring at room temperature for 2-6 hours. Pouring into water, carrying out suction filtration and drying to obtain an intermediate 2;
step three: iv adding 2-6mmol of an electron donor with borate groups, 1mmol of intermediate 2 and the phase transfer catalyst tetrabutylammonium hexaphosphate to 10mL of K2CO3Mixed solution of the water solution and 30mL of toluene at 75-105 DEG CAnd reacting for 24-48 hours. After the reaction is finished, cooling to room temperature, and adding H2Quenching O, extracting with dichloromethane, removing the solvent from the organic phase, and purifying the obtained solid with ethyl acetate and dichloromethane as eluent through a silica gel column to obtain an intermediate 3;
step four: v in the absence of light and N2Under the protection condition, 1-1.5mmol of the intermediate 1 synthesized in the step one and 1mmol of the intermediate 3 synthesized in the step three are dissolved in 20mL of glacial acetic acid and 60mL of chloroform solution and reacted for 4-8 hours at 70 ℃. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into water. Filtering out the separated solid, washing with water and cold methanol, and purifying the obtained solid by using dichloromethane and ethyl acetate as eluent through a silica gel column to obtain the near-infrared TADF organic luminescent material;
wherein N is a nitrogen atom; h is a hydrogen atom; s is a sulfur atom; o is an oxygen atom; br is a bromine atom.
Wherein i is Heck coupling reaction under the action of thionyl chloride; ii, carrying out reduction reaction under the action of iron powder; iii is an oxidation reaction under the action of chromium trioxide; (ii) a iv is in Pd (PPh)3)4Carrying out Suzuki coupling reaction under the catalysis; v is the Mannich reaction under the action of acetic acid.
The present invention is further illustrated by the following specific examples, which are not intended to limit the scope of the invention.
Example 1
Example 1.1:
in the absence of light and N2Under the protection condition, monomers of 4, 5-dinitro-1, 2-aminobenzene (5g,25.25mmol), 60mL of toluene and 60mL of thionyl chloride are added into a dry reaction bottle and reacted for 36 hours at 90 ℃. All solvents were removed and iron powder (15g,0.27mol) and 60ml acetic acid were added to the reaction flask in the dark and reacted at 80 ℃ for 4 h. Cooling to room temperatureAdding H2Quench O, extract with DCM and remove solvent to give a crude solid which is purified by column chromatography using Ethyl Acetate (EAC) and Methanol (MT) as eluent to give yellow intermediate monomer 1(3.02g, 72% yield).1H NMR(400MHz,DMSO)6.74(s,2H),5.81(s,4H).13C NMR(100MHz,CDCl3)146.03,134.08,109.28.MS(MALDI-TOF,m/z)[M]+Calcd for C6H6N4S,166.03；found 166.17.
Example 1.2:
5, 6-dibromoacenaphthene (10g,32mmol), chromium trioxide (19.2g,192mmol) and 150mL acetic anhydride were added to a dry reaction flask and reacted at 70 ℃ for 2 h. After the reaction is finished, cooling to room temperature, and adding H2O (400mL), followed by the slow addition of the appropriate amount of concentrated HCl and stirring at room temperature for 2 h. Pouring into 200mL of water, suction filtering, and drying to obtain yellow intermediate monomer 2(8.14g, 74% yield).1H NMR(400MHz,DMSO)8.35(d,J＝7.5Hz,2H),7.96(d,J＝7.5Hz,2H).MS(MALDI-TOF,m/z)[M]+Calcd for C12H4Br2O2,337.86；found 337.61.
Example 1.3:
in the absence of light and N2Under the protection condition, respectively adding
(1.8g,4.94mmol), intermediate 2(700mg,2.06mmol), Pd as catalyst (PPh)3)4(114.6mg,0.1mmol), phase transfer catalyst TBAB (64.4mg,0.2mmol) in a two-necked flask, sparged with deoxygenated 2M K2CO3The solution (20mL) and toluene solution (60mL) were reacted at 95 ℃ for 24 h. After the reaction is finished, cooling to room temperature, and adding H2Quenching O with DCM, removing the solvent from the organic phase and coloring the solid with PE and DCM as eluentsColumn purification gave the corresponding dark red precursor 3(950mg, 69% yield).
Example 1.4:
precursor 3(840mg,1.26mmol), intermediate 1(255mg,1.51mmol), glacial acetic acid (25mL) and chloroform solution (75mL) were added to the reaction flask under the protection of light and reacted for 4h at 70 ℃. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into 200mL of water. The separated solid was filtered off, washed with water, cold methanol and the solid obtained was purified by column chromatography using DCM and EAC as eluent to give the corresponding red target compound IR-1(523mg, 52% yield).1H NMR(400MHz,CD2Cl2)8.85(s,2H),8.47(d,J＝7.1Hz,2H),7.85(d,J＝6.9Hz,2H),7.25(d,J＝7.0Hz,16H),7.07(d,J＝7.5Hz,8H),6.90(d,J＝7.9Hz,4H).MS(MALDI-TOF,m/z)[M]+Calcd for C54H34N6S:798.23；found:798.26.
Example 2
2.1 preparation of intermediates 1, 2.2 methods for preparation of intermediate 2 were the same as 1.1, 1.2 in example 1.
Example 2.3:
in the absence of light and N2Under the protection condition, respectively adding
(1.2g,2.78mmol), intermediate 2(350mg,1.03mmol), Pd as catalyst (PPh)3)4(114.6mg,0.1mmol), phase transfer catalyst TBAB (64.4mg,0.2mmol) in a two-necked flask, sparged with deoxygenated 2M K2CO3The solution (10mL) and toluene solution (30mL) were reacted at 95 ℃ for 24 h. After the reaction is finished, cooling to room temperature, and adding H2Extracting with DCM, removing solvent from the organic phase to obtain solid, and purifying with column chromatography using PE and DCM as eluent to obtain corresponding dark redPrecursor 4(490mg, 67% yield).
Example 2.4:
precursor 4(200mg,0.22mmol), intermediate 1(41.5mg,0.25mmol), glacial acetic acid (5mL), and chloroform solution (15mL) were added to the reaction flask under the protection of light and reacted at 70 ℃ for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into 200mL of water. The separated solid was filtered off, washed with water, cold methanol and the solid obtained was purified by column chromatography using DCM and EAC as eluent to give the corresponding red target compound IR-2(143mg, 49% yield).1H NMR(400MHz,CDCl3)9.02(s,2H),8.63(s,2H),7.88(d,J＝7.1Hz,2H),7.19–7.13(m,8H),6.95(d,J＝8.7Hz,4H),6.87–6.77(m,12H),3.83(s,12H).MS(MALDI-TOF,m/z)[M]+Calcd for C58H42N6O4S:918.30；found:918.44.
Example 3:
3.1 preparation of intermediates 1, 3.2 methods for preparation of intermediate 2 were the same as 1.1, 1.2 in example 1.
Example 3.3:
in the absence of light and N2Under the protection condition, respectively adding
(1g,2.44mmol), intermediate 2(420mg,1.22mmol), Pd as catalyst (PPh)3)4(114.6mg,0.1mmol), phase transfer catalyst TBAB (64.4mg,0.2mmol) in a two-necked flask, sparged with deoxygenated 2M K2CO3The solution (10mL) and toluene solution (30mL) were reacted at 95 ℃ for 24 h. After the reaction is finished, cooling to room temperature, and adding H2Quenching with DCM extraction and organic phase removal of solvent the resulting solid was purified by column chromatography using PE and DCM as eluents to give the corresponding dark red precursor 5(622mg, 68% yield).
Example 3.4:
precursor 5(240mg,0.28mmol), intermediate 1(45mg,0.3mmol), glacial acetic acid (5mL), and chloroform solution (15mL) were added to the reaction flask under the protection of light, and reacted at 70 ℃ for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into 200mL of water. The separated solid was filtered off, washed with water, cold methanol and the solid obtained was purified by column chromatography using DCM and EAC as eluent to give the corresponding red target compound IR-3(110mg, 46% yield).1H NMR(400MHz,CDCl3)8.99(s,2H),8.66(d,J＝7.3Hz,2H),8.03(d,J＝7.3Hz,2H),7.60(d,J＝8.2Hz,4H),7.36(d,J＝7.3Hz,4H),7.26(s,4H),6.80–6.72(m,8H),6.20(d,J＝7.8Hz,4H),1.69(s,12H).MS(MALDI-TOF,m/z)[M]+Calcd for C60H42N6S:878.32.；found:878.55.
Example 4:
4.1 preparation of intermediates 1, 4.2 methods for preparation of intermediate 2 were the same as 1.1, 1.2 in example 1.
Example 4.3:
in the absence of light and N2Under the protection condition, respectively adding
(1g,2.6mmol), intermediate 2(350mg,1.03mmol), Pd as catalyst (PPh)3)4(114.6mg,0.1mmol), phase transfer catalyst TBAB (64.4mg,0.2mmol) in a two-necked flask, sparged with deoxygenated 2M K2CO3The solution (10mL) and toluene solution (30mL) were reacted at 95 ℃ for 24 h. After the reaction is finished, cooling to room temperature, and adding H2Quenching with DCM extraction and organic phase removal of solvent the resulting solid was purified by column chromatography using PE and DCM as eluents to give the corresponding dark red precursor 6(460mg, 65% yield).
Example 4.4:
precursor 6(600mg,0.75mmol), intermediate 1(153mg,1mmol), glacial acetic acid (15mL), and chloroform solution (45mL) were added to the reaction flask, respectively, under the protection of light, and reacted at 70 ℃ for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into 200mL of water. The separated solid was filtered off, washed with water, cold methanol and the solid obtained was purified by column chromatography using DCM and EAC as eluent to give the corresponding red target compound IR-4(300mg, 61% yield).1H NMR(400MHz,CDCl3)9.00(s,2H),8.67(d,J＝7.2Hz,2H),7.99(d,J＝7.3Hz,2H),7.48(d,J＝8.2Hz,4H),7.21(d,J＝8.2Hz,4H),6.63–6.57(m,12H),6.01(d,J＝5.9Hz,4H).MS(MALDI-TOF,m/z)[M]+Calcd forC54H30N6O2S:826.22；found:826.42.
Example 5:
5.1 preparation of intermediates 1, 5.2 methods for preparation of intermediate 2 were the same as 1.1, 1.2 in example 1.
Example 5.3:
in the absence of light and N2Under the protection condition, respectively adding
(1g,2.6mmol), intermediate 2(350mg,1.03mmol), Pd as catalyst (PPh)3)4(114.6mg,0.1mmol), phase transfer catalyst TBAB (64.4mg,0.2mmol) in a two-necked flask, sparged with deoxygenated 2M K2CO3The solution (10mL) and toluene solution (30mL) were reacted at 95 ℃ for 24 h. After the reaction is finished, cooling to room temperature, and adding H2Quenching O was extracted with DCM and the solid obtained after removal of the solvent from the organic phase was purified by column chromatography using PE and DCM as eluent to give the corresponding dark red precursor 7(440mg, 62% yield).
Example 5.4:
precursor 7(550mg,0.65mmol), intermediate 1(130mg,0.75mmol), glacial acetic acid (13mL), and chloroform solution (39mL) were added to the reaction flask under the protection of light, and reacted at 70 ℃ for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into 200mL of water. The separated solid was filtered off, washed with water, cold methanol and the solid obtained was purified by column chromatography using DCM and EAC as eluent to give the corresponding red target compound IR-5(240mg, 67% yield).1H NMR(400MHz,CDCl3)8.90(s,2H),8.45(d,J＝7.3Hz,2H),7.73(d,J＝7.3Hz,2H),7.39(d,J＝7.8Hz,6H),7.18(d,J＝7.1Hz,4H),7.02(d,J＝7.1Hz,2H),6.95–6.83(m,4H),6.71–6.57(m,4H),6.04(d,J＝7.8Hz,4H).MS(MALDI-TOF,m/z)[M]+Calcd for C54H30N6S3:858.17；found:858.37.
An emission spectrogram of IR-1 in the D-A type near-infrared organic luminescent material obtained in the experiment is shown as 12, wherein an emission peak of the IR-1 in a solution state is 617nm, an emission peak of the IR-1 in a thin film state is 690nm, and a remarkable red shift of 73nm is shown.
The solution state emission spectrum of the D-A type near infrared organic luminescent material obtained in the experiment is shown as 14, and the emission spectrum of the material solution state shows that the emission peaks are 610-710nm, wherein IR-1 is 617nm, IR-2 is 682nm, IR-3 is 617nm, IR-4 is 697nm, and IR-5 is 704 nm.
The above are embodiments of the present invention, it should be noted that the present invention is not limited to these examples, and these examples are only for better understanding of the present invention, and any equivalent changes made according to the technical scheme of the present invention are within the protection scope of the present invention.
Claims (10)
1. A preparation method of a D-A type near-infrared organic luminescent material is characterized by comprising the following steps:
the method comprises the following steps: preparation of intermediate 1
i. Carrying out Heck coupling reaction on monomer 4, 5-dinitro-1, 2-aminobenzene under the action of toluene and thionyl chloride;
ii, adding acetic acid, and carrying out reduction reaction under the action of iron powder to obtain an intermediate 1;
step two: iii, carrying out oxidation reaction on 5, 6-dibromo acenaphthene in an acetic anhydride solution under the action of chromium trioxide to prepare an intermediate 2;
step three: carrying out Suzuki coupling reaction on the intermediate 2 and the electron donor with the borate group under the action of a phase transfer catalyst to prepare an intermediate 3;
step four: v, carrying out Mannich reaction on the intermediate 1 and the intermediate 3 under the action of glacial acetic acid to obtain the near-infrared TADF organic luminescent material.
2. The method for preparing the D-A type near-infrared organic luminescent material according to claim 1, wherein the specific reaction formula is as follows:
wherein Ar is a strong electron donating group.
3. The method according to claim 2, wherein Ar is selected from one of the following chemical structures:
4. a method for preparing the D-a type near-infrared organic light emitting material according to claim 1, comprising the steps of:
the method comprises the following steps: under the conditions of light protection and nitrogen protection, dissolving the monomer 4, 5-dinitro-1, 2-aminobenzene in toluene and thionyl chloride, and reacting for 12-36 hours at 70-110 ℃; removing all solvents, adding iron powder and acetic acid into the reaction bottle under the condition of keeping out of the sun, and reacting for 4-8 hours at the temperature of 60-80 ℃; after the reaction is finished, purifying by a silica gel column to obtain an intermediate 1;
step two: dissolving 5, 6-dibromoacenaphthene and chromium trioxide in acetic anhydride, and reacting for 2 hours at 70-110 ℃; after the reaction is finished, cooling to room temperature, and adding H2O, then slowly adding concentrated hydrochloric acid, and stirring at room temperature for 2-6 hours; pouring into water, carrying out suction filtration and drying to obtain an intermediate 2;
step three: adding an electron donor with a borate group, intermediate 2 and a phase transfer catalyst to K2CO3Reacting for 24-48 hours at 75-105 ℃ in the mixed solution of the aqueous solution and the toluene; after the reaction is finished, cooling to room temperature, and adding H2Extracting the O quenching by using dichloromethane, removing the solvent from the organic phase, and purifying the obtained solid by using a silica gel column to obtain an intermediate 3;
step four: in the absence of light and N2Under the protection condition, dissolving the intermediate 1 synthesized in the step one and the intermediate 3 synthesized in the step three in a glacial acetic acid and chloroform solution, and reacting for 4-8 hours at the temperature of 60-80 ℃; after the reaction is finished, cooling to room temperature, and pouring into water; filtering out the separated solid, washing and purifying by a silica gel column to obtain the D-A type organic luminescent material.
5. The preparation method of the D-A type near-infrared organic luminescent material as claimed in claim 1, wherein in the first step, the molar ratio of the iron powder to the 4, 5-dinitro-1, 2-amino is 8:1 to 16:1, 3 to 6L of thionyl chloride is added to each mole of the 4, 5-dinitro-1, 2-amino, and the volume ratio of the toluene to the thionyl chloride is 1: 1.
6. The preparation method of the D-A type near-infrared organic luminescent material as claimed in claim 1, wherein in the second step, the molar ratio of each mole of chromium trioxide to 5, 6-dibromoacenaphthene is 6: 1-12: 1, and 4-6L of acetic anhydride is added to each mole of 5, 6-dibromoacenaphthene.
7. The method for preparing the D-A type near-infrared organic luminescent material according to claim 1, wherein in the third step, the molar ratio of the electron donor with the borate group to the intermediate 2 is 2: 1-6: 1, and the reaction is carried out between toluene and 2MK2CO3The aqueous solution is carried out in a mixed solution with the volume ratio of 3:1, and 30L of toluene solvent is added into each mol of the intermediate 2; the phase transfer catalyst is tetrabutyl ammonium hexaphosphate Pd (PPh)3)4。
8. The preparation method of the D-A type near-infrared organic luminescent material as claimed in claim 1, wherein in the fourth step, the molar ratio of the intermediate 1 to the intermediate 3 is 1: 1-1.5: 1, the reaction is carried out in a mixed solution composed of chloroform and glacial acetic acid according to the volume ratio of 3:1, and 20L of glacial acetic acid is added into each mole of the intermediate 3.
9. The D-A type near-infrared organic light emitting material prepared by the method according to any one of claims 1 to 8.
10. The D-A type near-infrared organic luminescent material as claimed in claim 9, for use in organic electroluminescent devices or organic semiconductor lasers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010546566.XA CN111574538A (en) | 2020-06-16 | 2020-06-16 | D-A type near-infrared organic luminescent material and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010546566.XA CN111574538A (en) | 2020-06-16 | 2020-06-16 | D-A type near-infrared organic luminescent material and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111574538A true CN111574538A (en) | 2020-08-25 |
Family
ID=72121900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010546566.XA Pending CN111574538A (en) | 2020-06-16 | 2020-06-16 | D-A type near-infrared organic luminescent material and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111574538A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751917A (en) * | 2022-04-21 | 2022-07-15 | 南京邮电大学 | Near-infrared luminescent fluorescent molecule and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105026518A (en) * | 2013-01-04 | 2015-11-04 | 日东电工株式会社 | Highly-fluorescent and photo-stable chromophores for wavelength conversion |
| CN107011365A (en) * | 2012-10-18 | 2017-08-04 | 精工爱普生株式会社 | Thiadiazoles system compound, light-emitting component compound, light-emitting component, light-emitting device, authentication device and electronic equipment |
| CN108409720A (en) * | 2018-04-10 | 2018-08-17 | 苏州大学 | Luminous organic material, the application of luminous organic material and organic electroluminescence device |
-
2020
- 2020-06-16 CN CN202010546566.XA patent/CN111574538A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011365A (en) * | 2012-10-18 | 2017-08-04 | 精工爱普生株式会社 | Thiadiazoles system compound, light-emitting component compound, light-emitting component, light-emitting device, authentication device and electronic equipment |
| CN105026518A (en) * | 2013-01-04 | 2015-11-04 | 日东电工株式会社 | Highly-fluorescent and photo-stable chromophores for wavelength conversion |
| CN108409720A (en) * | 2018-04-10 | 2018-08-17 | 苏州大学 | Luminous organic material, the application of luminous organic material and organic electroluminescence device |
Non-Patent Citations (1)
| Title |
|---|
| SONG, XIAOXIAN，等，: "A luminescent benzothiadiazole-bridging bis(salicylaldiminato)zinc(II) complex with mechanochromic and organogelation properties", 《DALTON TRANSACTIONS》, vol. 47, no. 17, 4 April 2018 (2018-04-04), pages 6146 - 6155 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751917A (en) * | 2022-04-21 | 2022-07-15 | 南京邮电大学 | Near-infrared luminescent fluorescent molecule and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112778327B (en) | Organic non-fullerene electron acceptor material and preparation method and application thereof | |
| CN105017302A (en) | Bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and preparation method and application thereof | |
| CN110407710B (en) | Triphenylamine derivative pure organic room temperature phosphorescent material and preparation method thereof | |
| CN111620817B (en) | Novel blue thermal activity delayed fluorescent material and application thereof | |
| CN111825634B (en) | Novel compounds, process for their preparation and their use | |
| CN113735855A (en) | Deep red/near infrared light thermal activation delayed fluorescent material, preparation method thereof and application thereof in organic electroluminescent material | |
| Liao et al. | Synthesis, optical and electrochemical properties of novel meso-triphenylamine-BODIPY dyes with aromatic moieties at 3, 5-positions | |
| CN101643381A (en) | Diarylfluorene intermediate preparation method | |
| CN112979687A (en) | Thermal activation delayed fluorescent material and preparation method and application thereof | |
| CN101550104B (en) | Benzene-naphthalene diimide derivative, preparation method and its application | |
| CN111574538A (en) | D-A type near-infrared organic luminescent material and preparation method and application thereof | |
| CN106632438B (en) | A kind of A- π-D- π-A type BODIPY derivatives and preparation method thereof based on acetenyl bridging | |
| CN110183361B (en) | Construction and application of cross-shaped thermal activity delay fluorescent material | |
| CN114249758B (en) | Dimer based on five-membered aromatic heterocyclic BODIPY and preparation method thereof | |
| WO2022121951A1 (en) | Boron-nitrogen compound, organic electroluminescence composition, and organic electroluminescence device containing same | |
| CN107236006B (en) | Red light metal complex and organic electroluminescent device thereof | |
| CN111423450B (en) | Compound, display panel and display device | |
| CN114874145A (en) | Water-soluble trityl free-based material and preparation method and application thereof | |
| CN115108919A (en) | Organic electroluminescent compound and organic electroluminescent device | |
| CN108558595B (en) | P-phenylene ethylene bridged trimer indene derivative and preparation method thereof | |
| Cheng et al. | Polybinaphthyls incorporating chiral 2, 2′-binaphthyl and isoquinoline moieties by Sonogashira reaction | |
| CN113321638A (en) | High-performance fluorescent dye suitable for various fluorescence detection scenes and preparation method thereof | |
| CN102850237B (en) | Method for preparing asymmetric spirobifluorene compound derived from functional group conversion on different fluorene ring | |
| CN105037167A (en) | Synthetic method of N, N-diaryl-2-bromine-6-naphthylamine and application thereof | |
| CN115490631B (en) | Near-infrared thermal activation delayed fluorescence luminescent material based on dicyanophenalene and application thereof |
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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200825 |
|
| RJ01 | Rejection of invention patent application after publication |