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Boron-containing organic electroluminescent material and application thereof in organic electroluminescent device

An electroluminescent material and luminescent technology, applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve the problems of low S1 state radiation transition rate, difficult high exciton utilization rate, high fluorescence radiation efficiency, and efficiency roll-off And other issues

Inactive Publication Date: 2020-06-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can A high T1→S1 state exciton conversion rate is achieved through the TADF process, but at the same time it leads to a low S1 state radiative transition rate. Therefore, it is difficult to achieve both (or simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) even Doped devices have been used to alleviate the T-exciton concentration quenching effect, and most devices made of TADF materials have a serious efficiency roll-off at high current densities

Method used

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  • Boron-containing organic electroluminescent material and application thereof in organic electroluminescent device
  • Boron-containing organic electroluminescent material and application thereof in organic electroluminescent device
  • Boron-containing organic electroluminescent material and application thereof in organic electroluminescent device

Examples

Experimental program
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Embodiment 1

[0084] Example 1: Example (1-1)-Example (1-23) shows the preparation methods for preparing intermediates (1-1) to (1-23), intermediates (1-1) to ( The structure of 1-23) is as follows:

[0085]

[0086]

Embodiment (1-1

[0087] Example (1-1): Preparation of Intermediate (1-1):

[0088]

[0089] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol 3-bromocarbazole, 0.012mol diphenylamine, 150ml toluene and stir and mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd(PPh 3 ) 4 , Heating to 105℃, refluxing reaction for 24 hours, sampling point plate, showing that no bromine is left, the reaction is complete; natural cooling to room temperature, filtering, filtrate under reduced pressure rotary evaporation (-0.09MPa, 85℃), passing neutral silica gel Column to obtain the target product; elemental analysis structure (molecular formula C 24 H 18 N 2 ): Theoretical value C, 86.20; H, 5.43; N, 8.38; Test value: C, 86.20; H, 5.42; N, 8.38. HPLC-MS: The molecular weight of the material is 334.15, and the measured molecular weight is 334.58.

Embodiment (1-2

[0090] Example (1-2): Preparation of Intermediate (1-2):

[0091]

[0092] In a nitrogen atmosphere, weigh out 0.01mol of 3-bromodibenzofuran, 0.015mol of bis(pinacol) diboron, 5×10 -4 molPd(dppf)Cl 2 Dissolve 0.02mol potassium acetate in 150ml 1,4-dioxane and react for 12 hours at 100°C. Sample point plates, complete the reaction, cool naturally, filter, and spin-evaporate the filtrate to obtain a crude product, which is passed through a neutral silica gel column. Get the intermediate 3-boronic acid dibenzofuran; elemental analysis structure (molecular formula C 12 H 9 BO 3 ): Theoretical value C, 67.98; H, 4.28; B, 5.10; Test value: C, 67.98; H, 4.28; B, 5.11. HPLC-MS: The molecular weight of the material is 212.06, and the measured molecular weight is 212.10.

[0093] In a 250mL three-necked flask, under the protection of nitrogen, add 0.01mol of 3-boronic acid dibenzofuran, 0.015mol of 2-nitrobromobenzene, dissolve it with a mixed solvent of toluene and ethanol (90mL of toluene...

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Abstract

The invention discloses a boron-containing organic electroluminescent material and application thereof in an organic electroluminescent device, the compound comprises boron groups, and the compound has strong group rigidity, and has the characteristics of difficult crystallization between molecules, difficult aggregation and good film-forming property. When the compound is used as a luminescent layer material of the organic electroluminescent device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, the service life of the device is obviously prolonged.

Description

Technical field [0001] The present invention relates to the field of semiconductor technology, in particular to an organic electroluminescent material containing boron and its application to organic electroluminescent devices. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a broad application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the purpose to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the posi...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/027C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1096C09K2211/104H10K85/657H10K85/6572H10K50/11
Inventor 李崇陈海峰叶中华王芳
Owner JIANGSU SUNERA TECH CO LTD
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