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Star-shaped thermal activation delayed fluorescence material, electronic device and application thereof

A technology of thermally activated delayed and fluorescent materials, applied in luminescent materials, electric solid-state devices, material analysis by optical means, etc., can solve the problems of low efficiency and low thermal stability, reduce overlap, improve device efficiency, The effect of reducing the energy level difference

Active Publication Date: 2020-06-05
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the above deficiencies in the prior art, the object of the present invention is to provide a novel acceptor-based TADF material, electronic devices and applications thereof, aiming to solve the problems of low thermal stability and low efficiency of existing TADF materials

Method used

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  • Star-shaped thermal activation delayed fluorescence material, electronic device and application thereof
  • Star-shaped thermal activation delayed fluorescence material, electronic device and application thereof
  • Star-shaped thermal activation delayed fluorescence material, electronic device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1: the preparation of compound 2:

[0064] (1) The preparation of intermediate 1-1, reaction formula is as follows:

[0065]

[0066] Add 1,3,5-triphenylbenzene (1.6g, 4.9mmol) and 4-fluorobenzenesulfonyl chloride (6.7g, 34mmol) into the two-necked flask, connect the condenser tube and connect it to the double-barrel tube, and communicate with argon gas protection. The flask was heated in an oil bath at 100°C for 5 minutes, then nitrobenzene (5 mL) was added, and anhydrous ferric chloride (0.56 g, 3.5 mmol) was added slowly, and heated and stirred at 100°C for 3 hours. The reaction solution was poured into 50 mL of methanol solution of hydrochloric acid (volume concentration 5%) and stirred vigorously, filtered, washed with 3% aqueous hydrochloric acid and deionized water, and dried in vacuo to obtain a brown crude solid. The crude product solid was dissolved in acetic acid, activated carbon was added to heat to reflux, and the acceptor intermediate 1-1 ...

Embodiment 2

[0070] Embodiment 2: the preparation of compound 60:

[0071] (1) The preparation of intermediate 2-1, the reaction formula is as follows:

[0072]

[0073] 1,3,5-tris(4-bromophenyl)benzene (500mg, 0.92mmol), (4-fluorophenyl)phenylphosphine (814mg, 3.7mmol), zinc powder (481mg, 7.4mmol), 2,2-bipyridine (115mg, 0.74mmol), nickel chloride hexahydrate (88mg, 0.37mmol) mixture was put into the two-necked bottle that is connected with condenser tube, added dimethylacetamide (20mL) under nitrogen protection, Stir at 150°C for 24 hours. After the reaction solution was cooled to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic layer was washed with MgSO 4 After drying and filtering, the crude product was separated by silica gel chromatography (eluent: methanol, dichloromethane) to obtain 310 mg of product with a yield of 35%. MS(MALDI-TOF):m / z 961.2[M + ].

[0074] (2) The preparation of compound 60, the reaction formula is a...

Embodiment 3

[0076] Embodiment 3: the preparation of compound 78:

[0077] (1) The preparation of intermediate 3-1, the reaction formula is as follows:

[0078]

[0079] 1,4-Dibromobenzene (472mg, 2.0mmol) was dissolved in anhydrous ether (4mL), and cooled to -78°C under nitrogen protection. A solution of isobutyllithium (1.4M in cyclohexane, 1.43 mL, 4.410 mmol) was added slowly. Slowly warm to 0°C over 2 hours, then cool again to -78°C. The reaction solution was added dropwise to a solution of 4-tert-butyl-2-methylphenylboronic acid (288 mg, 1.5 mmol) in dry ether (5 mL) at -78°C. The reaction solution was stirred overnight at room temperature after slowly warming up. 1M aqueous hydrochloric acid (5 mL) was added to terminate the reaction, and stirred at room temperature for 15 minutes. The organic layer was collected, the aqueous layer was extracted three times with ether, all organic layers were combined, dried over anhydrous sodium sulfate and concentrated by rotary evaporation...

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Abstract

The invention provides a star-shaped thermal activation delayed fluorescence material, an electronic device and an application thereof, which belong to the technical field of organic electroluminescence. The thermal activation delayed fluorescence material has the following structure: a star-shaped triphenylbenzene derivative compound disclosed by the invention has the property of thermal activation delayed fluorescence; a nitrogen-containing heterocyclic ring is used as an electron donor (Donor); the compound is connected with an electron-deficient receptor group, and the D-A type molecules with intramolecular charge transfer are formed; meanwhile, a large torsion angle between D and A is used for reducing molecular front line orbit overlapping, so that the singlet state-triplet state energy level is reduced, triplet state excitons can return to the singlet state through reverse intersystem crossing and finally return to the ground state in a radiation transition mode to emit fluorescence, the exciton utilization rate is increased, and finally the purpose of improving the device efficiency is achieved.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to thermally activated delayed fluorescent materials based on novel acceptors, electronic devices and applications thereof. Background technique [0002] Organic light-emitting diodes (organic light-emitting diodes, OLED), with its advantages of active light emission, fast response, large viewing angle, low driving voltage, energy saving, thinner and thinner, and flexible display, can meet consumers' demands for display technology. The new requirements have broad application prospects in the field of lighting displays, and the market demand is huge. [0003] In recent years, although OLED technology has made great progress, the development of OLEDs is still largely restricted by the dominant organic light-emitting guest materials. The traditional fluorescent materials used in the first generation of OLED materials are limited by spin statistics, the ratio of elec...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07C225/22C07C317/36C07D209/86C07D209/88C07D219/02C07D221/20C07D241/46C07D265/38C07D279/22C07D333/76C07D335/16C07D409/14C07D413/14C07D519/00C07F5/02C07F9/64C07F9/6596C09K11/06G01N21/64H01L51/54
CPCC07D265/38C07D279/22C07D219/02C07F7/0816C07D209/86C07D241/46C07D409/14C07D209/88C07D221/20C07D519/00C07F9/6596C07C225/22C07D413/14C07D333/76C07F9/64C07F5/027C07D335/16C07C317/36C09K11/06G01N21/64G01N21/6456C07B2200/05C09K2211/1037C09K2211/1033C09K2211/1007C09K2211/1014C09K2211/1044C09K2211/1029C09K2211/104C09K2211/1059C09K2211/1092H10K85/631H10K85/654H10K85/6576H10K85/657H10K85/40H10K85/6572
Inventor 曹啸松肖然杨楚罗
Owner SHENZHEN UNIV
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