CN111440187B - Thermal excitation blue light delaying material and preparation method and application thereof - Google Patents
Thermal excitation blue light delaying material and preparation method and application thereof Download PDFInfo
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- CN111440187B CN111440187B CN201911268332.7A CN201911268332A CN111440187B CN 111440187 B CN111440187 B CN 111440187B CN 201911268332 A CN201911268332 A CN 201911268332A CN 111440187 B CN111440187 B CN 111440187B
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- benzofuran
- blue light
- thieno
- dioxide
- benzothiophenes
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- 239000000463 material Substances 0.000 title claims abstract description 41
- 230000005284 excitation Effects 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 230000003111 delayed effect Effects 0.000 claims abstract description 25
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- FGOHSAGDFRKUEF-UHFFFAOYSA-N [1]benzothiolo[3,2-b][1]benzofuran 10,10-dioxide Chemical compound C1=CC=CC2=C1S(C1=C2OC2=C1C=CC=C2)(=O)=O FGOHSAGDFRKUEF-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 238000013508 migration Methods 0.000 abstract description 3
- 150000003457 sulfones Chemical class 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000000969 carrier Substances 0.000 abstract description 2
- 125000000468 ketone group Chemical group 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- RQYZJTUJRFVHEO-UHFFFAOYSA-N 2,7-dibromo-1-benzothiophene Chemical compound Brc1cc2cccc(Br)c2s1 RQYZJTUJRFVHEO-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- -1 2, 7-dibromo-benzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide Chemical compound 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZXVFTTRBWPOSLL-UHFFFAOYSA-N thieno[3,2-b][1]benzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CS2 ZXVFTTRBWPOSLL-UHFFFAOYSA-N 0.000 description 2
- NAXSBBMMIDFGHQ-UHFFFAOYSA-N 1,8-dimethyl-9h-carbazole Chemical compound N1C2=C(C)C=CC=C2C2=C1C(C)=CC=C2 NAXSBBMMIDFGHQ-UHFFFAOYSA-N 0.000 description 1
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 1
- CVHBCNYGVVJRGC-UHFFFAOYSA-N N1=C(C=CC=C1)C[Ir] Chemical compound N1=C(C=CC=C1)C[Ir] CVHBCNYGVVJRGC-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000005525 hole transport Effects 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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Abstract
The invention relates to a thermal excitation blue light delaying material and a preparation method and application thereof. The invention takes benzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide as an electron acceptor, and compared with the traditional electron acceptor such as sulfone or ketone group, the invention has a rigid plane structure, thereby being beneficial to not only fluorescence and stability, but also the migration of carriers; meanwhile, the difference between the triplet state energy level and the singlet state energy level of the molecule is small, and the TADF molecule is favorably constructed. The prepared thermal excitation delayed blue light material has the advantages of high luminous efficiency and stable performance.
Description
Technical Field
The invention relates to the technical field of organic luminescent materials, in particular to a thermal excitation blue light delaying material and a preparation method and application thereof.
Background
Since the discovery of Organic Light Emitting Diodes (OLEDs), organic light emitting devices mainly use organic light emitting small molecules and high molecular polymers as light emitting materials, and are prepared by evaporation or spin coating. However, due to poor solubility of organic light-emitting small molecules, the fluorescent material has low light-emitting efficiency (the traditional fluorescent efficiency is not more than 25%), the phosphorescent material generally contains precious metals (iridium, platinum and the like), and the conditions required by the evaporation process are harsh, so that the manufacturing process cost of the organic light-emitting device is extremely high.
Currently, the commercial blue-light material bis (4, 6-difluorophenylpyridine-N, C2) picolinyliridium (FirPic) of the OLED cannot meet the requirements of the market in terms of blue-light purity and luminous efficiency. The Adachi group designs and synthesizes a series of organic light-emitting small molecular materials of deep blue light based on a TADF (thermally excited delayed fluorescence) mechanism, and devices prepared from the materials can have the External Quantum Efficiency (EQE) of more than 20 percent, and the blue purity and the EQE are higher than those of commercial materials. However, the existing TADF blue light material generally has the problems of poor luminous purity, poor stability and the like.
Accordingly, there is a need for improvements and developments in the art.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a thermal excitation delayed blue light material, and a preparation method and application thereof, and aims to solve the problems of poor light-emitting purity and poor stability of the existing TADF blue light material.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a thermal excitation delayed blue light material has a molecular structural formula as follows:
wherein R is 1 、R 2 、R 3 Is an aromatic system unit.
The thermal excitation delayed blue light material, wherein R 1 、R 2 、R 3 Each independently is any one of the following aromatic system units:
the thermal excitation delayed blue light material has a molecular structural formula of any one of the following molecular formulas:
a method for preparing a thermally-excited delayed blue light material, wherein the method comprises the steps of:
dissolving [1] benzothiophene [3,2-b ] [1] benzofuran in chloroform, dropwise adding a chloroform solution of liquid bromine into the chloroform solution, reacting, adding a saturated sodium thiosulfate aqueous solution, washing, and drying to obtain 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
dissolving the 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran in acetic acid, adding 30% hydrogen peroxide, refluxing at a first preset temperature, pouring into water after the reaction is finished, and performing suction filtration and separation to obtain 2, 7-dibromo-benzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide;
dissolving the 2, 7-dibromobenzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide and an aromatic system unit in toluene, adding a catalyst, heating to a second preset temperature under the protection of inert gas, washing, drying, concentrating and carrying out column chromatography treatment after the reaction is finished to obtain the 2, 7-arylamine substituted benzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide.
A method for preparing a thermally-excited delayed blue light material, wherein the method comprises the steps of:
dissolving [1] benzothiophene [3,2-b ] [1] benzofuran in chloroform, dropwise adding a chloroform solution of liquid bromine with the same molar mass at 0 ℃, adding a saturated sodium thiosulfate aqueous solution, washing, and drying to obtain 2-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
dissolving the 2-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran in acetic acid, adding 30% hydrogen peroxide, refluxing at a first preset temperature, pouring into water after the reaction is finished, and performing suction filtration and separation to obtain 2-dibromo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide;
2-dibromobenzo [4,5]]Thieno [3,2-b ]]The benzofuran 10, 10-dioxide and aromatic system unit are dissolved in toluene, and Pd (PPh) is added 3 ) 4 And potassium carbonate, heating to a second preset temperature under the protection of inert gas, washing, drying, concentrating and carrying out column chromatography treatment after the reaction is finished to obtain 2-arylamine substituted benzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide.
The preparation method of the thermal excitation delayed blue light material is characterized in that the first preset temperature is 80-100 ℃, and the second preset temperature is 100-120 ℃.
The preparation method of the thermal excitation delay blue light material is characterized in that the reflux time is 5-8h.
The preparation method of the thermal excitation blue light delaying material is characterized in that the catalyst is Pd 2 (dba) 3 ，HF 4 P(t-Bu) 3 And potassium tert-butoxide.
The preparation method of the thermal excitation delayed blue light material is characterized in that the aromatic system unit is any one of the following organic molecules:
a light-emitting device comprises a cathode, a light-emitting layer and an anode from top to bottom in sequence, wherein the light-emitting layer is made of the thermal excitation delayed blue light material.
Drawings
FIG. 1 is a thermogravimetric analysis curve of a thermally-excited delayed blue light material in example 1 of the present invention.
FIG. 2 is a fluorescence emission spectrum of a thermally-excited delayed blue-light material in an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer and clearer, the present invention is further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
The thermal excitation delayed blue light material provided by the embodiment of the invention has the following molecular structural formula:
wherein R is 1 、R 2 、R 3 Is an aromatic system unit. Benzo [4,5] in the molecular Structure]Thieno [3,2-b ]]The benzofuran 10, 10-dioxide has excellent fluorescence property, has a rigid planar structure compared with a traditional electron acceptor such as sulfone or ketone, is not only favorable for fluorescence and stability, but also favorable for carrier migration, and simultaneously has good electron and hole transport capability.
In particular, R 1 、R 2 、R 3 Wherein R is 1 、R 2 May be the same or different, R 1 、R 2 、R 3 Each independently is any one of the following aromatic system units:
the aromatic system unit is selected as an electron donor, and the aromatic group in the aromatic system unit can provide abundant electrons for the electron acceptor, so that the obtained thermally-excited delayed blue light material has high stability in structure.
In one or more embodiments, the molecular formula of the thermally-excited delayed blue light material of the present invention may be any one of the following molecular formulas:
based on the same inventive concept, the invention also provides a preparation method of the thermal excitation delayed blue light material, which comprises the following preparation steps:
dissolving [1] benzothiophene [3,2-b ] [1] benzofuran in chloroform, dripping chloroform solution of liquid bromine at low temperature (about 0 ℃) until the raw materials react completely, and adding saturated sodium thiosulfate aqueous solution to reduce excessive liquid bromine. Washing the organic phase with saturated sodium bicarbonate water solution, drying, and purifying to obtain 2, 7-dibromo 1 benzothiophene 3,2-b 1 benzofuran.
2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran is dissolved in acetic acid, and 30% hydrogen peroxide is added to be heated and refluxed for 6 hours. Pouring into water after the reaction is finished, separating out solid, performing suction filtration separation, recrystallizing by using chloroform and petroleum ether, and purifying to obtain 2, 7-dibromobenzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide.
Buchward coupling: the bromobenzo [4,5] obtained above was reacted]Thieno [3,2-b ]]Benzofuran 10,10-dioxide and aromatic electron donating group are dissolved in toluene, and after removing oxygen in the system, a catalytic amount of Pd is added 2 (dba) 3 ，HF 4 P(t-Bu) 3 Heating and reacting with potassium tert-butoxide under the protection of inert gas until the reaction of the raw materials is finished; cooling to room temperature, washing with saturated brine and water, drying over anhydrous sodium sulfate, concentrating, eluting the residue with petroleum ether and dichloromethaneColumn chromatography to obtain 2, 7-arylamine substituted benzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide.
The specific synthetic route is as follows:
in another embodiment, the method for preparing the thermally-excited delayed blue light material comprises the following steps:
dissolving [1] benzothiophene [3,2-b ] [1] benzofuran in chloroform, dropwise adding a chloroform solution of liquid bromine with the same molar mass at low temperature until the raw materials completely react, and adding a saturated sodium thiosulfate aqueous solution to reduce the excessive liquid bromine. And washing the organic phase with saturated sodium bicarbonate water solution, drying and purifying to obtain 2-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran for later use.
Dissolving 2-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran in acetic acid, adding 30% hydrogen peroxide, and heating and refluxing for 6h. Pouring into water after the reaction is finished, separating out solids, performing suction filtration and separation, recrystallizing by using chloroform and petroleum ether, and purifying to obtain the 2-dibromobenzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide.
Suzuki coupling: the bromobenzo [4,5] obtained above was reacted]Thieno [3,2-b ]]Benzofuran 10,10-dioxide, an aromatic electron-donating borate group was dissolved in toluene, and after removing oxygen from the system, a catalytic amount of Pd (PPh) was added 3 ) 4 And potassium carbonate, heating and reacting under the protection of inert gas until the reaction of the raw materials is finished; cooling to room temperature, washing with saturated brine and water, drying over anhydrous sodium sulfate, concentrating, and subjecting the residue to column chromatography with petroleum ether and dichloromethane as eluent to obtain 2-substituted benzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide.
The specific synthetic route is as follows:
the embodiment of the invention also provides application of the thermal excitation delayed blue light material, and the thermal excitation delayed blue light material has good fluorescence and stability, and can be used as a light emitting layer of an OLED light emitting device because the difference between the triplet state energy level and the singlet state energy level of the molecule is small. Meanwhile, the material can also be used as a transmission layer of an organic photoelectric device due to good carrier transmission characteristics.
The present invention is explained in detail below by way of specific examples.
Example 1
The bromobenzo [4,5] obtained above was reacted]Thieno [3,2-b ]]Benzofuran 10,10-dioxide (2.07g, 5 mmol) and 1, 8-dimethylcarbazole (1.95g, 10 mmol) were dissolved in 60ml of toluene, and after removing oxygen in the system, pd was added 2 (dba) 3 (3％-5％)，HF 4 P(t-Bu) 3 (10% -15%) and potassium tert-butoxide (1.68g, 15mmol) under the protection of inert gas, and heating until the reaction of the raw materials is finished; then, the mixture was cooled to room temperature, washed with saturated brine and water, dried over anhydrous sodium sulfate, concentrated, and the residue was subjected to column chromatography using petroleum ether and dichloromethane as eluents to obtain compound 1 in 83% yield.
Performance testing
As shown in FIG. 1, compound 1 is excellent in thermal stability and has a thermal decomposition temperature exceeding 530 ℃. The powder fluorescence quantum yield of compound 1 was tested by integrating sphere and was 75%.
As can be seen from FIG. 2, the fluorescence spectra of the undoped and doped thin films were measured for a thin film having a thickness of 50nm by vacuum evaporation, and the undoped thin film had an emission peak of 453nm and a half-width of 60nm, and the thin film doped with DPEPO had an emission peak of 420nm and a half-width of 50nm.
In summary, the invention provides a thermally-excited delayed blue light material, and a preparation method and application thereof. The invention takes benzo [4,5] thieno [3,2-b ] benzofuran 10, 10-dioxide as an electron acceptor, and compared with the traditional electron acceptor such as sulfone or ketone group, the invention has a rigid plane structure, thereby being beneficial to not only fluorescence and stability, but also the migration of carriers; meanwhile, the difference between the triplet state energy level and the singlet state energy level of the molecule is small, and TADF molecules can be constructed beneficially. The prepared thermal excitation delayed blue light material has the advantages of high luminous efficiency and stable performance.
Meanwhile, the material can also be used as a transmission layer of an organic photoelectric device due to good carrier transmission characteristics.
It will be understood that the invention is not limited to the examples described above, but that modifications and variations will occur to those skilled in the art in light of the above teachings, and that all such modifications and variations are considered to be within the scope of the invention as defined by the appended claims.
Claims (4)
1. A thermal excitation delayed blue light material is characterized in that the molecular structural formula is as follows:
2. a method of preparing a thermally-excited delayed blue light material as claimed in claim 1, wherein the method comprises the steps of:
will [1]]Benzothiophenes [3,2-b ]][1]Dissolving benzofuran in chloroform, adding dropwise liquid bromine in chloroform for reaction, adding saturated sodium thiosulfate aqueous solution, washing, and drying to obtain 2, 7-dibromo [1]Benzothiophenes [3,2-b ]][1]A benzofuran; said [1]]Benzothiophenes [3,2-b ]][1]Benzofuran is
(ii) a The 2, 7-dibromo [1]]Benzothiophenes [3,2-b ]][1]Benzofuran is->
；
Reacting the 2, 7-dibromo [1]]Benzothiophenes [3,2-b ]][1]Dissolving benzofuran in acetic acid, adding 30% hydrogen peroxide, refluxing at a first predetermined temperature, and pouring into water after reactionFiltering and separating to obtain 2, 7-dibromobenzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide; the 2, 7-dibromobenzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide is
；
Reacting the 2, 7-dibromobenzo [4,5]]Thieno [3,2-b ]]Dissolving benzofuran 10, 10-dioxide and aromatic system unit in toluene, adding catalyst, heating to second predetermined temperature under inert gas protection, washing, drying, concentrating, and performing column chromatography to obtain 2, 7-arylamine substituted benzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide; the aromatic system unit is
(ii) a Said 2, 7-arylamine substituted benzo [4,5]]Thieno [3,2-b ]]Benzofuran 10, 10-dioxide as->
；
The catalyst is Pd 2 (dba) 3 ，HF 4 P(t-Bu) 3 And potassium tert-butoxide.
3. The method of claim 2, wherein the first predetermined temperature is 80-100 ℃ and the second predetermined temperature is 100-120 ℃.
4. A method of preparing a thermally-activated delayed blue light material as claimed in claim 3, wherein the reflow time is 5-8h.
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