Multi-resonance type thermally activated delayed fluorescence material with spatial three-dimensional structure, electronic device and application of multi-resonance type thermally activated delayed fluorescence material

A thermal activation delay and spatial three-dimensional technology, applied in the direction of luminescent materials, electric solid-state devices, semiconductor devices, etc., can solve the problems of reducing the efficiency of OLED devices, and achieve the goals of improving solubility and thermal stability, good comprehensive performance, and increasing lifespan Effect

CN113651841AActive Publication Date: 2021-11-16SHENZHEN UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2021-11-16

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Abstract

The invention discloses a multi-resonance type thermally activated delayed fluorescence material with a spatial three-dimensional structure, an electronic device and application of the multi-resonance type thermally activated delayed fluorescence material. The material has one of the structural general formulas shown in specification, wherein at least one of R1-R5 is one of the structures shown in specification. The three-dimensional rigid structure can inhibit the aggregation of molecules and avoid the aggregation-induced fluorescence quenching effect caused by intermolecular accumulation of the multi-resonance type thermally activated delayed fluorescence material, thereby improving the efficiency of the device. The peripheral unit of the three-dimensional structure is also beneficial to improving the solubility and the thermal stability of the thermally activated delayed fluorescence material, so that the service life of the device can be effectively prolonged.
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Description

technical field

[0001] The invention relates to the technical field of organic electroluminescent materials, in particular to multiple resonance thermally activated delayed fluorescent materials with spatial three-dimensional structures, electronic devices and applications thereof. Background technique

[0002] Organic light-emitting diodes (organic light-emitting diodes, OLED) have the advantages of bright colors, fast response, large viewing angle, low driving voltage, energy saving, thin and light, and flexible display. Among them, the light-emitting layer material is the core part of OLED. The early OLED light-emitting materials are traditional fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, traditional fluorescent materials can only use singlet states. Excitons emit light, therefore, the theoretical internal quantum efficiency of OLEDs of traditional fluorescent materials is 25%. Due to the spin-orbit coupling effect of heavy ato...

Examples

Embodiment 1

[0038] The specific synthesis process of the above-mentioned thermally activated delayed fluorescent material compound (4) is as follows:

[0039]

[0040] Preparation of Compound 2: Take a 100mL two-necked flask, add 2-bromotriptycene (1.67g, 5mmol), pinacol diboronate (1.30g, 5.1mmol), potassium acetate (0.98g, 10mmol) under the protection of argon ), Pd(dppf) 2 Cl 2 (0.36g, 0.5mmol) and 25mL of 1,4-dioxane, reacted at 100°C for 8 hours, cooled to room temperature, filtered through diatomaceous earth, and extracted three times with DCM (dichloromethane) and water . The combined organic phases were washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified by silica gel column chromatography using DCM / PE (v / v=1 / 4) as eluent to obtain 1.7 g of white solid with a yield of 90%.

[0041] 1 H NMR (500MHz, CDCl 3 )δ[ppm]: 7.26–7.31(m,4H),7.22–7.18(m,2H),7.13(d,J=8.2Hz,2H),7.10–7.08(m,2H),7.2(d,J =8.6Hz, 1H), 5.18(t, J=6.9H...

Embodiment 2

[0049] The specific synthesis process of the above-mentioned thermally activated delayed fluorescent material compound (8) is as follows:

[0050]

[0051] Preparation of compound 3: Take a 100mL two-necked flask, add compound 2 (2.26g, 5mmol), triptycene (1.75g, 5.1mmol), palladium acetate (0.05g, 0.25mmol), sodium tert-butoxide under the protection of argon (0.75g, 8mmol), tri-tert-butylphosphonium tetrafluoroborate (0.14g, 0.5mmol) and 25mL of anhydrous toluene were stirred and refluxed for 24 hours. After cooling to room temperature, it was filtered off through celite and extracted three times with DCM and water. The combined organic phases were washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified by silica gel column chromatography using DCM / PE (v / v=1 / 3) as eluent to obtain 2.44 g of white solid with a yield of 90%.

[0052] 1 H NMR (500MHz, CDCl 3 )δ[ppm]: 8.56–8.51(m,2H),7.92–7.88(m,4H),7.76(d,J=8.2Hz,1H),7....

Embodiment 3

[0057] The specific synthesis process of the above-mentioned thermally activated delayed fluorescent material compound (27) is as follows:

[0058]

[0059] The preparation of compound 3: get 100mL two-necked flask, add compound 2 (2.26g, 5mmol) under argon protection, compound 3 (2.23g, 5.1mmol), palladium acetate (0.05g, 0.25mmol), sodium tert-butoxide ( 0.75 g, 8 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.14 g, 0.5 mmol) and 25 mL of anhydrous toluene were stirred and refluxed for 24 hours. After cooling to room temperature, it was filtered off through celite and extracted three times with DCM and water. The combined organic phases were washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified by silica gel column chromatography using DCM / PE (v / v=1 / 3) as eluent to obtain 3.09 g of white solid with a yield of 75%.

[0060] 1 H NMR (500MHz, CDCl 3 )δ[ppm]: 8.76–8.61(m,2H),7.76(d,J=8.2Hz,4H),7.65–7.54(m,2H),7...