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D-pi-A type AIE-TADF near-infrared luminescent material as well as preparation method and application thereof

A luminescent material, near-infrared technology, applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the high cost of transition metal complex phosphorescent materials, heavy metal environmental pollution, and the difficulty of obtaining organic near-infrared luminescent materials High-efficiency luminescence, reduction of luminous efficiency of organic near-infrared luminescent materials and other issues, to achieve excellent carrier transport performance, reduce non-radiative transitions, and promote the effect of reverse intersystem jumping

Active Publication Date: 2021-06-04
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the luminous efficiency of organic fluorescent materials is low, the cost of transition metal complex phosphorescent materials is high, and there are environmental pollution problems of heavy metals.
[0005] Due to the limitation of the energy gap law, the luminous efficiency of organic near-infrared luminescent materials usually decreases with the increase of luminous wavelength.
In order to reduce the energy gap, organic near-infrared light-emitting materials inevitably need to introduce a large planar conjugated system. Although these materials have strong light emission in the solution state, they are prone to aggregation-caused luminescence quenching in the thin film state. quenching, ACQ) phenomenon, which makes it difficult for organic near-infrared luminescent materials to obtain high-efficiency luminescence

Method used

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  • D-pi-A type AIE-TADF near-infrared luminescent material as well as preparation method and application thereof
  • D-pi-A type AIE-TADF near-infrared luminescent material as well as preparation method and application thereof
  • D-pi-A type AIE-TADF near-infrared luminescent material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of DPA-ThPh-QCN, the synthetic route is as follows:

[0037]

[0038] Preparation of 6-(4-bromophenyl)quinoxaline-2,3-dicarbonitrile (1)

[0039] In a 500mL two-necked flask, add diaminomaleonitrile (20.0g, 92.5mmol), acetonitrile (350mL), stir to dissolve, add dichlorodicyanobenzoquinone (DDQ) (42.0g), and stir at room temperature for 30min After filtration, the filtrate was concentrated and dried to obtain a reddish-brown solid, which was directly used in the next step without further purification. The intermediate product oxalimide dicyanide (22.0g, 207mmol) and 4-bromo-o-phenylenediamine (25.8g, 118mmol) were mixed, and trifluoroacetic acid (500mL) was added in batches, stirred at room temperature for 8h, and then poured into ice water , filtered, washed. Separation by column chromatography (PE / EA=5 / 1) afforded 12.0 g of an off-white solid (compound 1) (yield: 50.0%). 1H NMR (400MHz, DMSO) δ8.69 (d, J = 2.0Hz, 1H), 8.37 (dd, J = 9.0, 2.1Hz, 1H)...

Embodiment 2

[0055] DPA-ThPh-QCN and (OMe) in embodiment 1 2 AIE performance test of DPA-ThPh-QCN:

[0056] Make DPA-ThPh-QCN into 10 -5 M tetrahydrofuran / water (THF / H 2 O) mixed solution, measure the photoluminescence property of different ratio water content respectively at room temperature, as figure 2 with image 3 shown.

[0057] from figure 2 It can be seen that: when the excitation wavelength is 500nm, DPA-ThPh-QCN in f w (Water content) w When it is 70%, a stronger emission peak appears at 680nm; when f w =90%, the emission intensity is the largest, the luminous intensity is increased by 14 times, and the maximum emission peak is red-shifted by 10nm. Water content (f w ) and luminous intensity (I / I 0 ), water content (f w ) and the maximum emission peak wavelength as image 3 shown.

[0058] When the excitation wavelength is 500nm, (OMe) 2 DPA-ThPh-QCN also showed a similar phenomenon, such as Figure 4 shown in f w In w =80%, a stronger emission peak appears at 70...

Embodiment 3

[0060] DPA-ThPh-QCN and (OMe) in embodiment 1 2 TADF characteristic test of DPA-ThPh-QCN:

[0061] Combine DPA-ThPh-QCN and (OMe) 2 The film made of DPA-ThPh-QCN is evenly adsorbed on the inner wall of the small test tube, sealed and deoxygenated for more than 30 minutes. Measure its transient decay life at room temperature and nitrogen atmosphere, such as Figure 7 shown.

[0062] from Figure 7It can be seen from the figure that the transient decay lifetime curve of the DPA-ThPh-QCN thin film in a nitrogen atmosphere presents an obvious second-order exponential decay, and the data fitting results show a longer delayed lifetime: T d = 26 μs. Similarly, if Figure 7 As shown, (OMe) 2 The transient attenuation lifetime curve of DPA-ThPh-QCN solid thin film presents obvious second-order exponential attenuation. d = 19 μs. Microsecond-scale lifetimes indicate typical TADF features.

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Abstract

The invention belongs to the technical field of luminescence and display, and particularly relates to a D-pi-A type AIE-TADF near-infrared luminescent material and a preparation method and application thereof. According to the near-infrared luminescent material, phenyl dicyanoquinoxaline with strong electron absorption is used as an acceptor (A) unit, and triarylamine[diphenylthiophenamine, di(4-methoxyphenyl)thiophenamine and di(4-fluorophenyl)thiophenamine] with strong electron donating is used as a donor (D) unit. The near-infrared luminescent material is high in thermal stability and has excellent carrier transport performance and photoluminescence performance, and the fluorescence quantum efficiency of the near-infrared luminescent material is 27%, so that the near-infrared luminescent material is widely applied to the fields of organic electroluminescent displays, biological imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of luminescence and display lighting, and in particular relates to a D-π-A type AIE-TADF near-infrared luminescent material, a preparation method thereof and an application in a near-infrared organic electroluminescent device. Background technique [0002] Aggregation-induced emission (AIE) is an effective method to suppress concentration quenching to obtain efficient solid-state luminescence. Since Tang Benzhong's team first reported the AIE phenomenon in 2001, AIE molecules have attracted the attention of researchers because of their high-efficiency light-emitting properties in solid thin films, and have been widely used in organic light-emitting diodes (OLEDs). So far, the AIE fluorescent materials that have been reported mainly include cyanobenzoate, tetraphenylstyrene and o-carborane derivatives, etc. They are used in non-doped OLEDs to achieve full-color display. However, AIE fluorescent materials ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10C09K11/06H01L51/50H01L51/54
CPCC07D409/10C09K11/06C09K2211/1092C09K2211/1044H10K85/655H10K85/636H10K85/6572H10K50/11
Inventor 朱卫国孙俊兰吴秀刚王亚飞张斌朱梦冰刘煜谭华
Owner CHANGZHOU UNIV
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