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Blue thermal activity delayed fluorescent material based on dibenzoheterocycle conjugated pi bridge, and application thereof

A technology of delayed fluorescence and fluorescent materials, applied in the field of organic electroluminescent materials, which can solve the problems of increased non-radiative transitions, reduction of material luminous efficiency, and large increase in vibration intensity, to achieve the effect of suppressing non-radiative transitions and improving luminous efficiency

Active Publication Date: 2021-12-14
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although TADF materials have made major breakthroughs from the blue light to the near-infrared region, most of the reported TADF blue light materials are highly twisted between the intramolecular donor and acceptor, and the intramolecular vibration intensity increases greatly, thereby increasing the non-radiative transition. The luminous efficiency of the material

Method used

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  • Blue thermal activity delayed fluorescent material based on dibenzoheterocycle conjugated pi bridge, and application thereof
  • Blue thermal activity delayed fluorescent material based on dibenzoheterocycle conjugated pi bridge, and application thereof
  • Blue thermal activity delayed fluorescent material based on dibenzoheterocycle conjugated pi bridge, and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Taking formula I as an example, the synthesis scheme of TADF blue light material based on dibenzoheterocyclic conjugated π bridge is as follows:

[0027]

[0028] Synthesis of compound SM1

[0029] Add thiophenol (1.53g, 13.8mmol), 1-bromo-2-fluoro-4-iodobenzene (5g, 16.6mmol), cuprous iodide (0.53g, 2.8mmol), o- Phenanthroline (0.5 g, 2.8 mmol), sodium tert-butoxide (6.7 g, 69.2 mmol), and 100 mL of analytically pure toluene were heated to reflux at 120° C. for 24 hours under nitrogen protection. Cool to room temperature, remove toluene by rotary evaporation under reduced pressure, extract with dichloromethane (3×50mL), wash with water three times, dry over anhydrous magnesium sulfate, filter, collect the filtrate, spin dry the solvent, and use petroleum ether as the eluent for column chromatography 3.5 g of a colorless oily liquid were isolated with a yield of 89.5%. 1H NMR (300MHz, CDCl3) δ7.93(d, J=7.0Hz, 2H), 7.81(d, J=8.6Hz, 2H), 7.67–7.51(m, 4H).

[0030] A...

Embodiment 2

[0042] Compound 1 in Example 1 was crystallized from chloroform / methanol mixed solvent by solvent evaporation method, and its crystal structure was obtained by X-ray single crystal diffraction as follows: figure 1 shown. The single crystal structure of compound 1 shows that it is a dimer, and there are two conformations in the molecular structure, and the dihedral angles are 106.07° and 81.03°, respectively.

Embodiment 3

[0044] Compound SM4, SM5 and compound 1 in embodiment 1 are dissolved in toluene to form 10 -5 M solution, test the UV-Vis absorption and photoluminescence spectra of its solution. Depend on figure 1 It can be seen that there are roughly two absorption peaks in the UV-Vis absorption spectrum of the compound in solution: the absorption peak at the short wavelength (300nm) is mainly attributed to the π-π* transition absorption of the molecule; the absorption peak at the long wavelength (370nm) is attributed to Intramolecular charge transfer (ICT) transition absorption peak from donor unit to acceptor unit. like figure 2 As shown, the maximum emission peak of compound SM4 is 445nm, the emission peak of compound SM5 is 478nm, and the emission peak of compound 1 is 465nm, indicating that the three compounds are all in the blue light emission region.

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Abstract

The invention belongs to the technical field of organic electroluminescent materials, and particularly discloses a blue thermal activity delayed fluorescent material based on a dibenzoheterocycle conjugated pi bridge, and application thereof. The blue thermal activity delayed fluorescent material is a novel blue light TADF material which takes an arylamine derivative as a donor unit, sulfone as an acceptor unit and dibenzoheterocycle as a conjugated pi bridge. The dibenzoheterocycle conjugated pi bridge has a relatively large planar rigid structure, is beneficial to inhibition of non-radiative transition of molecules and improvement of the luminous efficiency of the TADF material, can also obtain a relatively small delta EST value, and is beneficial to construction of an efficient blue TADF material. The novel blue light TADF material is used as a luminescent layer dopant to prepare a solution processing type electroluminescent device, and the maximum external quantum efficiency of more than 20% is obtained. The relationship between the molecular structure and the performance is discussed in detail, and has important significance for constructing an efficient blue-light TADF material.

Description

technical field [0001] The invention relates to a class of organic thermally active delayed fluorescence (TADF) materials, mainly a class of dibenzoheterocyclic rigid units as π bridges, arylamine derivatives as electron donors, and diphenyl sulfone derivatives as electron acceptors The blue organic thermally active delayed fluorescent material and its application in organic electroluminescent devices belong to the technical field of organic electroluminescent materials. Background technique [0002] Thermally activated delayed fluorescent materials have a theoretical internal quantum efficiency of 100% and do not contain heavy metal atoms, and are known as the third-generation organic electroluminescent materials. Since 2009, Adachi's research group at Kyushu University in Japan applied thermally activated delayed fluorescence (TADF) materials to organic light-emitting diodes (OLEDs) for the first time, which opened a research boom on TADF materials and their devices. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D409/04C09K11/06H01L51/50H01L51/54
CPCC07D405/04C07D409/04C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092H10K85/636H10K85/6576H10K85/6574H10K85/6572H10K50/11Y02E10/549
Inventor 王亚飞朱媛媛朱卫国
Owner CHANGZHOU UNIV
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