CN112979687B - Thermal activation delay fluorescent material and preparation method and application thereof - Google Patents

Thermal activation delay fluorescent material and preparation method and application thereof Download PDF

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CN112979687B
CN112979687B CN202110226814.7A CN202110226814A CN112979687B CN 112979687 B CN112979687 B CN 112979687B CN 202110226814 A CN202110226814 A CN 202110226814A CN 112979687 B CN112979687 B CN 112979687B
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CN112979687A (en
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杨楚罗
吕夏蕾
曹啸松
杨熠宇
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Shenzhen Lide Photoelectric Technology Co ltd
Shenzhen University
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Shenzhen University
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Abstract

The invention provides a thermal activation delay fluorescent material, a preparation method and application thereof, wherein the structure of the thermal activation delay fluorescent material is shown as a formula I. The electronic device prepared from the thermal activation delay fluorescent material provided by the invention has the advantages of narrower half-peak width, lower starting voltage, high luminous efficiency and longer service life of the device, and is simple to prepare and convenient to synthesize.

Description

Thermal activation delay fluorescent material and preparation method and application thereof
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to a thermally activated delayed fluorescent material and a preparation method and application thereof, in particular to a narrow-band emission thermally activated delayed fluorescent material and a preparation method and application thereof.
Background
In recent years, research on organic light emitting diodes (Organic Light Emitting Diode, abbreviated as OLEDs) has made a major breakthrough, and has shown attractive industrialized prospects in the fields of display and illumination. Since the light emitting material is a basic stone of OLED industry, development of high-performance light emitting material is a goal commonly pursued by the scientific research and industry.
In 2009, the Adachi group of subjects used for the first time molecules with the thermally activated delayed fluorescence (thermally activated delayed fluorescence, TADF) phenomenon for OLED devices. The TADF luminescent molecule has smaller singlet-triplet state energy gap (delta EST), can enable triplet state to generate reverse intersystem transition (reverse intersystem-cross, RISC) to singlet state, and then forms singlet state exciton radiation luminescence, thereby realizing theoretical internal quantum efficiency of 100%. TADF materials draw great attention from researchers at home and abroad, and are also considered as third-generation luminescent materials with the most application prospect.
Thermally Activated Delayed Fluorescence (TADF) materials can be divided into two classes, one class being charge transfer TADF (CT-TADF) materials; the other is a multiple resonance TADF (MR-TADF) material. The main difference between the two is that the emission half-width of the CT-TADF material is wider, the color purity of the device is poorer, the latter adopts a polycyclic aromatic hydrocarbon skeleton to limit the rotation of molecules, and B atoms (acceptors) with electron deficiency and N atoms (donors) with electron enrichment are contained in the same core structure, so that the pure blue light or green light MR-TADF molecule (adv. Mater.2016,28,2777) with the emission spectrum half-width smaller than 30nm (half-width of the quantum dot material is reached) is obtained. Although the high color purity of the MR-TADF luminescent material has great advantages in display and illumination applications, the materials are difficult to synthesize, have few types and few long-wavelength luminescent compounds at present, and are still to be further developed. Therefore, how to provide an organic photoelectric material with narrow half-width, convenient synthesis, high luminous efficiency and long service life of devices becomes a problem to be solved urgently.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a thermally activated delayed fluorescence material and a preparation method and application thereof, in particular to a narrow-band emission thermally activated delayed fluorescence material and a preparation method and application thereof. The electronic device prepared from the thermal activation delay fluorescent material provided by the invention has the advantages of narrower half-peak width, lower starting voltage, high luminous efficiency and longer service life of the device, and is simple to prepare and convenient to synthesize.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a thermally activated delayed fluorescence material having a structure according to formula I:
wherein R is 1 、R 2 、R 3 Independently selected from any one of methyl, trifluoromethyl, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C2-C60 alkenylamino, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C2-C60 alkenyloxy, substituted or unsubstituted C4-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 aryloxy, substituted or unsubstituted C4-C60 arylamino, substituted or unsubstituted C4-C60 thioaryloxy, substituted or unsubstituted C4-C60 arylboron, substituted or unsubstituted C6-C60 aromatic ring, or substituted or unsubstituted C3-C60 aromatic heterocyclic.
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 Independently selected from any one of hydrogen, deuterium, halogen, cyano, amidino, hydrazino, hydrazone, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C2-C60 enamino, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C2-C60 alkenyloxy, substituted or unsubstituted C4-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 aryloxy, substituted or unsubstituted C4-C60 arylamino, substituted or unsubstituted C4-C60 thioaryloxy, or substituted or unsubstituted C4-C60 arylboron.
The electronic device prepared by the heat-activated delayed fluorescence material with the specific structure has the advantages of narrower half-peak width, lower starting voltage, high luminous efficiency and longer service life of the device.
Preferably, the structure of the thermally activated delayed fluorescence material is selected from Any one of them.
Wherein Y is 1 、Y 2 Independently selected from hydrogen, deuterium, -O-, -S-, -Se-, -s=o-, -SO 2 -、-C(R 4 R 5 )-、-Si(R 4 R 5 )-、-Ge(R 4 R 5 )-、-N(R 4 )-、-P(R 4 ) -or-p=o (R 4 ) -any one of R 4 、R 5 Independently selected from any one of hydrogen, deuterium, alkenyl, alkynyl, amino, nitro, carbonyl, sulfonyl, halogen, cyano, alkyl, alkoxy, substituted or unsubstituted C6-C60 aromatic ring group or substituted or unsubstituted C3-C60 aromatic heterocyclic group, R 1 、R 2 、R 3 Having the same limit as above, X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 Independently selected from any one of hydrogen, deuterium, halogen, cyano, amidino, hydrazino, hydrazone, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C2-C60 enamino, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C2-C60 alkenyloxy, substituted or unsubstituted C4-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 aryloxy, substituted or unsubstituted C4-C60 arylamino, substituted or unsubstituted C4-C60 thioaryloxy, or substituted or unsubstituted C4-C60 arylboron.
Preferably, the thermally activated delayed fluorescence material is selected from any one of the compounds 1 to 312, and the structures of the compounds 1 to 312 are as follows:
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in a second aspect, the present invention provides a method for preparing a thermally activated delayed fluorescence material as described above, the method comprising the steps of:
(1) Reacting the compound A with the compound B to obtain a compound C;
(2) And (3) treating the compound C obtained in the step (1) with an organolithium reagent, then carrying out lithium-boron metal exchange with boron tribromide, and then carrying out a serial type boron hybrid Friedel-crafts reaction to obtain the thermally activated delayed fluorescent material.
The reaction formula is shown as formula II:
wherein R is 1 、R 2 、R 3 Having the same limit as above, X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 、Y 1 、Y 2 Having the same limit as above, X 11 、X 12 、X 13 Independently selected from halogen.
The preparation method is simple to operate and convenient to synthesize, and the thermally activated delayed fluorescence material can be rapidly prepared.
In a third aspect, the present invention provides the use of a thermally activated delayed fluorescence material as described above in the preparation of an organic photovoltaic material.
In a fourth aspect, the present invention provides an electronic device comprising a substrate, a first electrode, an organic layer and a second electrode arranged in that order, the composition of the organic layer comprising a thermally activated delayed fluorescence material as described above.
Preferably, the organic layer includes any one or a combination of at least two layers of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, which are sequentially stacked from the side near the first electrode to the side near the second motor, for example, a combination of a hole injecting layer and a hole transporting layer, a combination of an electron injecting layer and an electron transporting layer, or a combination of a hole blocking layer and an electron blocking layer, etc., but not limited to the above-listed combinations, other non-listed combinations within the above-listed combinations are equally applicable.
Preferably, the light emitting layer includes a host material and a doped guest material.
Preferably, the composition of the luminescent layer comprises a thermally activated delayed fluorescence material as described above.
In a fifth aspect, the present invention also provides a display device comprising an electronic device as described above.
Compared with the prior art, the invention has the following beneficial effects:
(1) The thermal activation delay fluorescent material is prepared, and the prepared electric shock device has narrower half-peak width and obvious multiple resonance effect, so that a multiple resonance-thermal activation delay fluorescent material system and a luminescent color range are greatly enriched;
(2) The OLED device prepared by the thermal activation delay fluorescent material provided by the invention has the advantages of lower starting voltage, high luminous efficiency and longer service life, can meet the requirements of current panel manufacturing enterprises on high-performance luminescent materials, and has good application prospects.
Drawings
FIG. 1 is a graph of low temperature singlet and triplet test results for Compound 4;
FIG. 2 is a graph of low temperature singlet and triplet test results for compound 41;
FIG. 3 is a graph of the delayed fluorescence decay lifetime test results for Compound 4;
FIG. 4 is a graph of the delayed fluorescence decay lifetime test results for Compound 8;
FIG. 5 is a graph of the delayed fluorescence decay lifetime test results for compound 14;
FIG. 6 is a graph showing the results of a delayed fluorescence decay lifetime test of Compound 41.
Detailed Description
In order to further describe the technical means adopted by the present invention and the effects thereof, the following describes the technical scheme of the present invention in combination with the preferred embodiments of the present invention, but the present invention is not limited to the scope of the embodiments.
In the following preparation, the HPLC detection instrument was Agilent 1260Infinite HPLC system, flow rate 1.0mL/min, and sample injection amount 20. Mu.L.
Preparation example 1 preparation of Compound 1
The preparation scheme of compound 1 is as follows:
the method comprises the following specific steps:
(i) In a dry 100ml two-necked flask, intermediate 1-1 (0.5 mmol), potassium tert-butoxide (1.1 mmol), and anhydrous CuSO were added 4 (0.025 mmol) was then dried under vacuum for 15min, 10mL of chlorobenzene was added under argon, heated to 90℃and stirred for 12 h. After the reaction, cooling, extracting with dichloromethane, spin-drying, and column chromatography with petroleum ether and dichloromethane to obtain intermediate 1-2 with 73% yield, MS (MALDI-TOF) m/z 234.58[ M+H ] + ]。
(ii) A100 mL dry, two-necked round bottom flask was prepared and intermediate 1-2 (2 mmol), intermediate 1-3 (1 mmol), csCO 3 (2.5 mmol) was added to the flask, connected to a condenser, degassed and purged with argon, and repeated three times. Dry DMF (50 mL) was added and refluxed under argon for 24h. Cooling the reaction solution to 25deg.C, adding water, separating out solid, dissolving with dichloromethane, rotary evaporating to remove solvent, purifying the crude product with silica gel column to obtain white solid, namely intermediate 1-4, with yield of 56%, MS (MALDI-TOF) m/z 575.62[ M+H ] + ]。
(iii) 1.5 g was added dropwise to a pressure-resistant flask containing tert-butylbenzene (150 mL) as an intermediate 1-4 (3 mmol) at-40℃under argonM in t-butyllithium pentane (6.6 mmol) and slowly warmed to 60℃and stirred for 5 hours. The components having a boiling point lower than that of t-butylbenzene are then distilled off under reduced pressure. Cooled to-40 ℃ and boron tribromide (7.5 mmol) was added, slowly warmed to 25 ℃ and stirred for 1 hour. The reaction was cooled again to 0deg.C and N, N-diisopropylethylamine (15 mmol) was added, slowly warmed to 25deg.C and sealed, and stirring was continued at 180deg.C for 24 hours. The reaction solution was then cooled to 25℃and quenched by dropwise addition of methanol, and the solvent was distilled off under reduced pressure. Further refining the residual crude product by silica gel column chromatography to obtain pale yellow solid, namely the compound 1 with the HPLC purity of 99.3 percent and the yield of 15 percent. MS (MALDI-TOF) m/z 549.81[ M+H ] + ]。
Preparation example 2 preparation of Compound 2
The preparation scheme for compound 2 is as follows:
the method comprises the following specific steps:
(i) Step (i) of preparation 1 was repeated except that intermediate 1-1 was replaced with an equivalent amount of intermediate 2-1 to obtain intermediate 2-2 in a yield of 64%, MS (MALDI-TOF) m/z 250.22[ M+H ] + ]。
(ii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 2-2 to obtain intermediate 2-3 in 57% yield, MS (MALDI-TOF) m/z 607.85[ M+H ] + ]。
(iii) The procedure of (iii) of preparation 1 was followed, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 2-3, to finally obtain compound 2 in 99.3% purity by HPLC and 13% yield. MS (MALDI-TOF): m/z 581.46[ M+H ] + ]。
Preparation example 3 preparation of Compound 4
The preparation scheme for compound 4 is as follows:
the method comprises the following specific steps:
(i) Step (i) of preparation example 1 was repeated in the same manner except that intermediate 1-1 was replaced with an equivalent amount of intermediate 3-1 to obtain intermediate 3-2 in a yield of 87%, MS (MALDI-TOF) m/z 283.65[ M+H ] + ]。
(ii) The procedure (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 3-2, to obtain intermediate 3-3 in 86% yield, MS (MALDI-TOF) m/z 673.59[ M+H ] + ]。
(iii) The procedure of (iii) of preparation 1 was followed, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 3-3, to finally obtain compound 4 in a purity of 99.3% by HPLC and a yield of 20%. MS (MALDI-TOF) m/z 647.81[ M+H ] + ]。
Preparation example 4 preparation of Compound 7
The preparation scheme for compound 7 is as follows:
the method comprises the following specific steps:
(i) The procedure (i) of preparation example 1 was repeated except that intermediate 1-1 was replaced with an equivalent amount of intermediate 4-1 to obtain intermediate 4-2 in 93% yield, MS (MALDI-TOF) m/z 208.23[ M+H ] + ]。
(ii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 4-2 to obtain intermediate 4-3 in 76% yield, MS (MALDI-TOF) m/z 523.24[ M+H ] + ]。
(iii) The procedure (iii) of preparation 1 was followed, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 4-3, to give compound 7 having an HPLC purity of 99.3% and a yield of 25%, MS (MALDI-TOF) m/z 497.85[ M+H ] + ]。
Preparation example 5 preparation of Compound 8
The preparation scheme for compound 8 is as follows:
the method comprises the following specific steps:
(i) Step (i) of preparation example 1 was repeated in the same manner except that intermediate 1-1 was replaced with an equivalent amount of intermediate 5-1 to obtain intermediate 5-2 in 83% yield, MS (MALDI-TOF) m/z 224.56[ M+H ] + ].
(ii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 5-2 to obtain intermediate 5-3 in a yield of 74%, MS (MALDI-TOF) m/z 555.38[ M+H ] + ]。
(iii) The procedure (iii) was followed in preparation example 1, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 5-3, to give compound 8 having an HPLC purity of 99.3% and a yield of 15%, MS (MALDI-TOF) m/z 529.67[ M+H ] + ]。
Preparation of Compound 10
The preparation scheme for compound 10 is as follows:
the method comprises the following specific steps:
(i) In a dry 100mL two-necked flask, intermediate 6-1 (1.0 mmol), intermediate 3-2 (1.0 mmol) and potassium carbonate (3.0 mmol) were added, followed by addition of 30mL of toluene, 15mL of ethanol and 15mL of water, followed by rapid stirring under nitrogen bubbling to remove oxygen and rapid addition of catalyst Pd (PPh 3 ) 4 (0.01 mmol) was connected to a condenser, heated to reflux under nitrogen protection, and reacted for 12 hours. After the reaction, cooling, extracting with dichloromethane, spin-drying, and column chromatography with petroleum ether and dichloromethane to obtain intermediate 6-3 with 92% yield, MS (MALDI-TOF) M/z315.59[ M+H ] + ]。
(ii) A100 mL dry, double neck round bottom flask was prepared, and intermediate 6-3 (2 mmol) and triphenylphosphine (6 mmol) were added to the flask, followed by a condenser, degassing and argon purging, and repeated three times. Dried o-dichlorobenzene (40 mL) was added and refluxed under argon for 36h. After the reaction solution was cooled to 25 ℃, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatographyA white solid was obtained, intermediate 6-4, in 74% yield, MS (MALDI-TOF) m/z 673.58[ M+H ] + ]。
(iii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 6-4 to obtain intermediate 6-5 in a yield of 74%, MS (MALDI-TOF) m/z 555.38[ M+H ] + ]。
(iv) The procedure (iii) of preparation 1 was followed, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 6-5, to give compound 10 having an HPLC purity of 99.3% and a yield of 15%, MS (MALDI-TOF): m/z 647.82[ M+H ] + ]。
Preparation example 7 preparation of Compound 13
The preparation scheme for compound 13 is as follows:
the method comprises the following specific steps:
(i) In a dry 100mL two-necked flask, intermediate 7-1 (1.0 mmol), intermediate 7-2 (1.0 mmol) and potassium carbonate (3.0 mmol) were added, followed by addition of 30mL of toluene, 15mL of ethanol and 15mL of water, followed by rapid stirring under nitrogen bubbling to remove oxygen and rapid addition of catalyst Pd (PPh 3 ) 4 (0.01 mmol) was connected to a condenser, heated to reflux under nitrogen protection, and reacted for 12 hours. After the reaction, cooling, extracting with dichloromethane, spin-drying, and column chromatography with petroleum ether and dichloromethane to obtain intermediate 7-3 with a yield of 47%, MS (MALDI-TOF) m/z 303.87[ M+H ] + ]。
(ii) The procedure (ii) of preparation example 6 was repeated except that intermediate 6-3 was replaced with an equivalent amount of intermediate 7-3, to obtain intermediate 7-4 in 25% yield, MS (MALDI-TOF) m/z 271.91[ M+H ] + ]。
(iii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 7-4 to obtain intermediate 7-5 in 74% yield, MS (MALDI-TOF) m/z 650.86[ M+H ] + ]。
(iv) Except that intermediate 1-4 was replaced with equivalent amount of intermediate 7-5, the remainder was preparedStep (iii) of example 1 was identical and gave compound 13 having an HPLC purity of 99.3%, yield 14%, MS (MALDI-TOF) m/z 624.82[ M+H ] + ]。
Preparation example 8 preparation of Compound 14
The preparation scheme for compound 14 is as follows:
the method comprises the following specific steps:
(i) In a dry 100mL two-necked flask, intermediate 8-1 (1.0 mmol), intermediate 8-2 (1.0 mmol) and potassium carbonate (3.0 mmol) were added, followed by addition of 30mL of toluene, 15mL of ethanol and 15mL of water, followed by rapid stirring under nitrogen bubbling to remove oxygen and rapid addition of catalyst Pd (PPh 3 ) 4 (0.01 mmol) was connected to a condenser, heated to reflux under nitrogen protection, and reacted for 12 hours. After the reaction, cooling, extracting with dichloromethane, spin-drying, and column chromatography with petroleum ether and dichloromethane to obtain intermediate 8-3 with 92% yield, MS (MALDI-TOF) m/z 256.87[ M+H ] + ]。
(ii) The procedure (ii) of preparation example 6 was repeated except that intermediate 6-3 was replaced with an equivalent amount of intermediate 8-3, to obtain intermediate 8-4 in 30% yield, MS (MALDI-TOF) m/z 224.61[ M+H ] + ]。
(iii) Step (ii) of preparation 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 8-4 to obtain intermediate 8-5 in 65% yield, MS (MALDI-TOF) m/z 555.64[ M+H ] + ]。
(iv) The procedure (iii) was followed in preparation example 1, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 8-5, to give compound 14 having an HPLC purity of 99.3% and a yield of 15%, MS (MALDI-TOF) m/z 529.34[ M+H ] + ]。
Preparation of Compound 52 from preparation example 9
The preparation scheme for compound 52 is as follows:
the method comprises the following specific steps:
(i) Step (i) of preparation example 1 was repeated except that intermediate 1-1 was replaced with an equivalent amount of intermediate 9-1 to obtain intermediate 9-2 in 95% yield, MS (MALDI-TOF) m/z 339.84[ M+H ] + ]。
(ii) The procedure (ii) of preparation example 1 was followed, except that intermediate 1-2 was replaced with an equivalent amount of intermediate 9-2 and intermediate 1-3 was replaced with an equivalent amount of intermediate 9-3, to obtain intermediate 9-4 in a yield of 70%, MS (MALDI-TOF) m/z 909.14[ M+H ] + ]。
(iii) The same procedure as in (iii) of preparation example 1 was repeated except that intermediate 1-4 was replaced with an equivalent amount of intermediate 9-4, to obtain intermediate 9-5, which had an HPLC purity of 99.3%, a yield of 32%, and MS (MALDI-TOF): m/z 837.54[ M+H ] + ]。
(iv) A100 mL dry, double neck round bottom flask was prepared, intermediate 9-5 (1 mmol) and CuCN (3 mmol) were added to the flask, a condenser was attached, degassing was performed, and nitrogen was vented, and the reaction was repeated three times. Dry DMF (50 mL) was added and stirred under nitrogen at 150 ℃ for 24h. After cooling the reaction mixture to 25℃and adding water, the solid is precipitated, dichloromethane is dissolved, the solvent is removed by rotary evaporation, and the crude product is purified by means of a silica gel column to give an orange powder, compound 52, HPLC purity 99.2%, yield 21%, MS (MALDI-TOF): M/z 784.56.[ M+H ] + ]。
Preparation of Compound 243
The preparation scheme of compound 243 is as follows:
the method comprises the following specific steps:
(i) A100 mL dry, two-necked round bottom flask was prepared and intermediate 3-2 (1 mmol), intermediate 10-1 (2 mmol), csCO 3 (2.5 mmol) was added to the flask, connected to a condenser, degassed and purged with argon, and repeated three times. Dry DMF (50 mL) was added and refluxed under argon for 24h. Cooling the reaction solution to 25 ℃, adding water, separating out solids, adding dichloroMethane was dissolved, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography to give a white solid, intermediate 10-2, in 72% yield, MS (MALDI-TOF) m/z 471.15[ M+H ] + ]。
(ii) Into a dry 100mL two-necked flask, intermediate 10-2 (1 mmol), sodium tert-butoxide (2.0 mmol), pd (OAc) were successively introduced 2 (0.025mmol)、(tBu 3 P)HBF 4 (0.0125 mmol) was added 30mL of dry toluene in the absence of oxygen, heated to 110℃and stirred for 24 hours. After the reaction, cooling, extracting with dichloromethane, spin-drying, and column chromatography with petroleum ether and dichloromethane to obtain intermediate 10-3 with 65% yield, MS (MALDI-TOF) m/z 662.17[ M+H ] + ]。
(iii) To a pressure-resistant flask containing tert-butylbenzene (150 mL) as intermediate 10-3 (3 mmol) was added dropwise 1.5M solution of tert-butyllithium pentane (6.6 mmol) under argon at-40℃and slowly warmed to 60℃and stirred for 5 hours. The components having a boiling point lower than that of t-butylbenzene are then distilled off under reduced pressure. Cooled to-40 ℃ and boron tribromide (7.5 mmol) was added, slowly warmed to 25 ℃ and stirred for 1 hour. The reaction was cooled again to 0deg.C and N, N-diisopropylethylamine (15 mmol) was added, slowly warmed to 25deg.C and sealed, and stirring was continued at 180deg.C for 24 hours. The reaction solution was then cooled to 25℃and quenched by dropwise addition of methanol, and the solvent was distilled off under reduced pressure. Further refining the remaining crude product by silica gel column chromatography (developing solvent: n-hexane/dichloromethane= (20:1)) to obtain pale yellow solid, namely compound 243, HPLC purity 99.3%, yield 15%, MS (MALDI-TOF): m/z 636.32[ M+H ] + ]。
Preparation of Compound 41
The preparation scheme for compound 41 is as follows:
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the method comprises the following specific steps:
(i) The procedure (i) was repeated except for replacing intermediate 1-1 with an equivalent amount of intermediate 11-1, to obtain intermediate 11-2 in 94% yield, MS (MALDI-TOF):m/z 339.24[M+H + ]。
(ii) The procedure (ii) of preparation example 1 was repeated except that intermediate 1-2 was replaced with an equivalent amount of intermediate 11-2, to obtain intermediate 11-3 in 79% yield, MS (MALDI-TOF) m/z 785.67[ M+H ] + ]。
(iii) The procedure (iii) of preparation 1 was followed, except that intermediate 1-4 was replaced with an equivalent amount of intermediate 11-3, to give compound 41 having an HPLC purity of 99.3%, a yield of 19%, and MS (MALDI-TOF): m/z 759.80[ M+H ] + ]。
Application examples 1 to 11 and comparative application example 1
Application examples 1-11 and comparative application example 1 provided an OLED, respectively, prepared as follows:
ITO (indium tin oxide) glass was ultrasonically cleaned in a cleaner and deionized water for 30 minutes. Then vacuum drying for 2 hours (105 ℃) and then placing ITO (indium tin oxide) glass into a plasma reactor for oxygen plasma treatment for 5 minutes, conveying the ITO (indium tin oxide) glass into a vacuum chamber to prepare an organic film and a metal electrode, then preparing a layer of 35nm hole transport material TAPC (4, 4 '-cyclohexyl di [ N, N-di (4-methylphenyl) aniline) by a vacuum evaporation method, evaporating 10nm thick electron blocking material TCTA (4, 4' -tris (carbazole-9-yl) triphenylamine), evaporating a luminescent layer taking mCBP (3, 3 '-bis (9H-carbazole-9-yl) -1,1' -biphenyl) as a main body, respectively doping the main body with 1, 2,4, 7, 8, 10, 13, 14, 41, 52, 243 and 4CzIPN (2, 4,5, 6-tetra (9-carbazolyl) -m-phenylenediamine), evaporating a layer of 10nm 2,4, 6-tris [3- (diphenylphosphino) phenyl ] -1,3, 5-triazine (TmCBP) as an electron blocking layer of which is formed by evaporation, and finally evaporating the luminescent layer taking the mCBP (3, 3 '-bis (9H-carbazole-9-yl) -1,1' -biphenyl) as an electron blocking layer of 100 nm.
The vacuum evaporator used in the OLED is a system prepared by Shenyang ultra-vacuum application technology research, and the evaporation process is 5×10 -4 Done under high vacuum at Pa and the evaporation rate of each material was monitored using Sigma SQM 160 film thickness monitor, liF evaporation rate wasThe evaporation rate of aluminum is->The evaporation rate of other materials is controlled to be +.>The prepared light-emitting device uses a Keithley2400 digital source table to provide voltage and monitor current, uses a Photometer search PR655 light amplitude meter to test properties such as brightness and spectrum, and obtains final device performance data including half-peak width, luminous efficiency and starting voltage through software control coordination calculation. All devices tested were not further treated and tested at between 20-30 c under one atmosphere.
Half-width, luminous efficiency and turn-on voltage were tested for the above OLEDs.
The materials, parameters and test results of the layers of the OLED are as follows:
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from the results, the thermal activation delay fluorescent material provided by the invention has the thermal activation delay fluorescent property and high external quantum efficiency, and compared with the electroluminescent device in the prior art, the prepared electroluminescent device has narrower half-peak width and lower starting voltage, and has important application value in constructing devices with high efficiency, high color purity and high stability.
Compound performance test:
the ultraviolet absorption spectra of compounds 4 and 41 were tested using a Shimadzu UV-2600 ultraviolet spectrophotometer, and the fluorescence and low Wen Linguang spectra of compounds 4 and 41 were tested using a Hitachi F-7100 fluorescence spectrometer. The singlet state and triplet state energy levels of the compound are obtained according to the wavelengths at the peaks of the fluorescence spectrum and the phosphorescence spectrum, and the results are shown in fig. 1 and 2 respectively. From fig. 1 and fig. 2, it can be seen that the difference between the singlet state and the triplet state of compounds 4 and 41 is less than 0.3eV, which indicates that it is beneficial to realize the transition from triplet state exciton to reverse system of singlet state exciton, thereby realizing 100% internal quantum efficiency, which is the result of the resonant molecular design of the thermally activated delayed fluorescent material provided by the invention, which is that the HOMO and LUMO electron cloud separation is relatively complete, thereby reducing the difference between the triplet state energy levels.
The delayed fluorescence decay lifetimes of compounds 4, 8, 14 and 41 were then tested using PicoQuant Fluotime and the results are shown in FIGS. 3-6, respectively. It can be seen from the graph that the thermally-activated delayed fluorescence material provided by the invention has a delayed lifetime, namely, the process that triplet excitons penetrate to singlet exciton reverse systems in the light emitting process and then emit light is directly demonstrated, and the thermally-activated delayed fluorescence material has the thermally-activated delayed fluorescence property.
The applicant states that the present invention is illustrated by the above examples of the thermally activated delayed fluorescence material of the present invention and the method of preparing the same and the use thereof, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further.

Claims (7)

1. A thermally activated delayed fluorescence material, wherein the structure of the thermally activated delayed fluorescence material is selected from the group consisting of:
2. use of a thermally activated delayed fluorescence material according to claim 1 for the preparation of an organic optoelectronic material.
3. An electronic device comprising a substrate, a first electrode, an organic layer, and a second electrode disposed in that order, wherein the composition of the organic layer comprises the thermally activated delayed fluorescence material of claim 1.
4. The electronic device according to claim 3, wherein the organic layer includes any one layer or a combination of at least two layers of a light-emitting layer, a hole-injecting layer, a hole-transporting layer, an electron-injecting layer, an electron-transporting layer, a hole-blocking layer, and an electron-blocking layer, which are stacked in this order from a side near the first electrode to a side near the second motor.
5. The electronic device of claim 4, wherein the light emitting layer comprises a host material and a doped guest material.
6. The electronic device according to claim 4 or 5, wherein the composition of the light-emitting layer comprises the thermally activated delayed fluorescence material of claim 1.
7. A display device, characterized in that it comprises an electronic device according to any of claims 3-6.
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