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Thermal activation delayed fluorescence material based on dibenzophenazine derivative as well as preparation method and application of thermal activation delayed fluorescence material

A thermally activated delay, benzophenazine technology, applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problem of poor rigid structure, inefficient long-wavelength TADF materials, low fluorescence quantum yield, etc. problem, to achieve the effect of good conjugation ability, excellent electroluminescence performance, and high solid-state fluorescence quantum efficiency

Active Publication Date: 2020-08-25
山西穿越光电科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Technical problem to be solved: Aiming at the problems in the prior art that the long-wave band TADF material is not efficient enough, the molecular rigid structure of the material is poor, and the fluorescence quantum yield is low, the present invention provides a thermally activated delayed fluorescence based on dibenzophenazine derivatives Materials and their preparation methods and applications. The prepared materials have electron acceptor and electron donor units exhibiting a highly twisted rigid structure, which can achieve 100% theoretical internal quantum efficiency, high fluorescence quantum yield, and provide high-efficiency long-band OLED devices. Advantages such as guarantee

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  • Thermal activation delayed fluorescence material based on dibenzophenazine derivative as well as preparation method and application of thermal activation delayed fluorescence material
  • Thermal activation delayed fluorescence material based on dibenzophenazine derivative as well as preparation method and application of thermal activation delayed fluorescence material
  • Thermal activation delayed fluorescence material based on dibenzophenazine derivative as well as preparation method and application of thermal activation delayed fluorescence material

Examples

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Effect test

Embodiment 1

[0041] The thermally activated delayed fluorescent material based on dibenzophenazine derivatives described in this example is DBP-3PXZ, and its structural formula is as follows:

[0042] .

[0043] The preparation method is:

[0044] (1) Add 3,6-dibromophenanthrene-9,10-dione (2 g, 5.46 mmol) into 100 mL of glacial acetic acid and stir to dissolve, then add 4-bromobenzene-1,2-diamine (1.2 g , 6.58 mmol) to react, the reaction temperature is 110 ℃, and the reaction time is 6 hours. After the reaction, the crude product is filtered by suction, washed with water, and dried to obtain the product: 3,6,11-tribromodibenzo[a , c] phenazine, yield 95%.

[0045] (2) Take the product 3,6,11-tribromodibenzo[a,c]phenazine (2 g, 3.87 mmol) and phenoxazine (2.83 g, 15.48 mmol) obtained in step (1) and add Stir in water toluene solution, add tri-tert-butylphosphine (1.16 mL, 11.61 mmol), potassium carbonate (3.2 g, 23.22 mmol) and palladium acetate (0.14 g, 0.6 mmol) to react under nitr...

Embodiment 2

[0057] The thermally activated delayed fluorescent material based on dibenzophenazine derivatives described in this example is DBP-3PTZ, and its structural formula is as follows:

[0058] .

[0059] The preparation method is the same as in Example 1, except that the reactant phenoxazine in step (2) is changed to phenothiazine, and the yield of the reactant is 52%. The molecular structure analysis results are as follows: DBP-3PTZ, mass spectrum: 871.19; elemental analysis: C: 77.13, H: 3.81, N: 8.03.

[0060] The application of the above-mentioned DBP-3PTZ thermally activated delayed fluorescent material based on dibenzophenazine derivatives in the preparation of wet-process organic electroluminescent diodes (OLED devices).

[0061] The schematic diagram of the prepared wet OLED device structure is as follows: from bottom to top, ITO anode 1, hole transport layer 2 (PEDOT:PSS (40 nm)), light emitting layer 3 (DBP-3PTZ (40 nm)), electron transport layer Layer 4 (PO-T2T (40 n...

Embodiment 3

[0065] The thermally activated delayed fluorescent material based on dibenzophenazine derivatives described in this embodiment is DBP-3ACR, and its structural formula is as follows: .

[0066] The preparation method is the same as in Example 1, except that the reactant phenoxazine in step (2) is changed to 9,10-dihydroacridine, and the yield of the reactant is 60%. The molecular structure analysis results are as follows: DBP-3ACR, mass spectrum: 902.16; elemental analysis: C: 86.54, H: 5.70, N: 7.76.

[0067] The application of the above-mentioned DBP-3ACR thermally activated delayed fluorescent material based on dibenzophenazine derivatives in the preparation of wet-process organic electroluminescent diodes (OLED devices).

[0068] The schematic diagram of the prepared wet OLED device structure is as follows: from bottom to top, ITO anode 1, hole transport layer 2 (PEDOT:PSS (40 nm)), light emitting layer 3 (DBP-3ACR (40 nm)), electron transport layer Layer 4 (PO-T2T (40 n...

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Abstract

The invention discloses a thermal activation delayed fluorescence material based on a dibenzophenazine derivative as well as a preparation method and application of the thermal activation delayed fluorescence material, and belongs to the technical field of organic photoelectric materials and devices. The structural formula of the material is shown as a formula (I), in the formula (I), R1 is phenoxazinyl, phenothiazinyl or dimethyl acridinyl, R1' is phenoxazinyl, phenothiazinyl or dimethyl acridinyl, R1 '' is phenoxazinyl, phenothiazinyl or dimethyl acridinyl, and R2 is H, phenoxazinyl, phenothiazinyl or dimethyl acridinyl. The material provided by the invention has the advantages that the electron acceptor and the electron donor unit show a highly distorted rigid structure, 100% theoretical internal quantum efficiency can be realized, the fluorescence quantum yield is high, a guarantee is provided for a high-efficiency long-waveband OLED device, and the like. And a polysubstitution mode is adopted, so that red shift of molecular emission wavelength is facilitated, long-waveband luminescence is realized, and a guarantee is provided for an efficient long-waveband OLED device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials and devices, and specifically relates to a thermally activated delayed fluorescent material based on dibenzophenazine derivatives, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs for short) have the advantages of high efficiency, low power consumption, wide viewing angle, bendability, and large-area display. They are known as the most promising solid-state lighting and information display of the new generation. After decades of hard work, the luminous efficiency and stability of OLED displays have basically met popular demands, and are widely used in instrumentation and high-end smartphones. As the core part of OLED devices, the light-emitting layer is the key research direction of the majority of scientific researchers. Thermally Activated Delayed Fluorescence (TADF) materials, as a way to use all-organic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D417/14C07D401/14C09K11/06H01L51/50H01L51/54
CPCC07D413/14C07D417/14C07D401/14C09K11/06C09K2211/1033C09K2211/1044C09K2211/1037C09K2211/1029H10K85/657H10K85/6572H10K50/11
Inventor 孙开涌滕玉玲周璐瑶许新悦蔡照胜
Owner 山西穿越光电科技有限责任公司
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