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Thermally-activated delayed fluorescence emission material and application thereof

A technology of thermal activation delay and fluorescence emission, which is applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of poor luminescence performance of acceptor units, and achieve lower exciton density, high glass transition temperature and thermal stability performance, the effect of suppressing efficiency roll-off

Active Publication Date: 2020-05-19
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among these materials, the conjugated system of the receptor unit constructed is relatively small, and the luminescence performance of the receptor unit itself is poor, so there are great challenges in realizing high-efficiency red light and near-infrared light.

Method used

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  • Thermally-activated delayed fluorescence emission material and application thereof
  • Thermally-activated delayed fluorescence emission material and application thereof
  • Thermally-activated delayed fluorescence emission material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment (I

[0066] Implementation example (I), the synthesis of I-1 and I-2

[0067]

[0068] The chemical synthesis of intermediate M1 refers to the literature report published by the inventor (J. Mater. Chem. C., 2019, 7, 9690).

[0069] Chemical synthesis of M2:

[0070] In a three-necked flask, add 0.888 g (3 mmol) of intermediate M1, 0.682 g (3.9 mmol, 1.3 eq) of NBS, and then add 25 ml of dichloromethane and 25 ml of DMF, and react at 45 ° C after nitrogen replacement. After the reaction was monitored by TCL, dichloromethane was distilled off, methanol was added to disperse, and a solid was obtained by filtration, which was recrystallized with dichloromethane to obtain 0.9 g of pure product. M2: 1H-NMR (300MHz CDCl3): δ (ppm) 8.67-8.74 (m, 2H,), 8.10-8.17 (m, 3H), 7.72-7.76 (m, 1H), 7.61-7.67 (m, 4H) ,7.49(s,1H). M2 NMR data such as figure 1 shown.

[0071] Chemical synthesis of I-2:

[0072] In a dry three-necked flask, replace the air with nitrogen, add 0.75g of intermedi...

Embodiment (2

[0075] The synthetic scheme of implementation example (2) compound 1-20

[0076]

[0077] In a dry three-necked flask, add intermediate M3 (0.562g), 3,6-dimethylcarbazole (0.858g), cesium carbonate (1.63g), DMF (30ml), replace the air with nitrogen, and heat to reflux React for 14 hours. After the TCL detection reaction is completed, cool down, add 100ml of water to the reaction system, and filter to obtain a solid. The obtained solid was separated and purified by column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain 0.3 g of I-20 product. M3 NMR data such as Figure 4 shown.

[0078] I-20: 1H-NMR (300MHz CDCl3): δ (ppm) 7.942-7.959 (m, 3H,), 7.875 (s, 2H), 7.568-7.586 (m, 2H), 7.435-7.453 (m, 1H) ,7.358-7.395(m,2H),7.178-7.218(m,3H),7.047-7.066(m,4H),6.885-6.905(m,2H),6.500-6.525(t,1H),2.527-2.534( d, 12H). The NMR data of I-20 is as follows Figure 5 shown.

Embodiment (3

[0079] Implementation example (3), the synthesis of I-33

[0080]

[0081] Synthesis of Intermediate M4

[0082] In a dry three-necked flask, replace the air with nitrogen, add 0.7g of 2,3-dichloroquinoxaline, 1.0g of 4-ethynyltriphenylamine, and 0.123g of Pd(PPh 3 ) 2 Cl 2 , 0.033g of CuI, 9mmol of triethylamine, and 10ml of acetonitrile. After nitrogen replacement, react at 60° C. for 8 hours, then add 30 ml of trifluoroacetic acid to the reaction system, and react for 4 hours. After the TCL detection reaction was completed, 100 ml of water was added to the reaction system, and the solid was obtained by filtration. The obtained solid was separated and purified by column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain 1.0 g of M4 product.

[0083] M4: 1H-NMR (300MHz CDCl3): δ (ppm) 8.188-8.208 (d, J = 8Hz, 1H,), 8.115-8.133 (d, J = 7.2Hz, 3H), 7.874-7.896 (d, J = 7.2Hz, 2H), 7.739-7.766(m, 2H), 7.348-7.386(m, 4H), 7....

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Abstract

The invention discloses a thermally-activated delayed fluorescence emission material and application thereof. Receptor units constructed through molecular design are multi-element aromatic fused heterocycles with high luminous efficiency; and a plurality of N heteroatoms, or N and O heteroatoms, or N and S heteroatoms introduced into a condensed ring system can adjust electron-deficient weak interactions of the receptor units and singlet-triplet state energy level difference in a molecular system, are beneficial for reverse inter-system jumping and conversion, and can regulate and control intermolecular C-H...Pi effect, hydrogen bond effect and local dipole-dipole interaction so as to allow material molecules to generate a stacking structure beneficial for aggregation-state efficient lightemitting, thereby achieving aggregation-state efficient light emitting.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a heat-activated delayed fluorescent emission material and its application. Background technique [0002] OLED (Organic light-emitting diode), the Chinese name organic light-emitting diode, is the most promising new information display technology and lighting technology after liquid crystal display. After more than 20 years of development, OLED has been applied in the fields of small information display such as mobile phone and camera display, but there are still key obstacles such as service life, device luminous efficiency, and product cost in the field of large-size information display and lighting applications. , failed to be fully commercialized. Material research plays a core and fundamental role in promoting the research process of OLEDs. After more than 20 years of development, OLEDs luminescent materials have experienced three ge...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D491/22C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D491/22C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1062C09K2211/1059H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 王栋东李毅祥汪新叶
Owner XI AN JIAOTONG UNIV
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