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Boron-containing multi-element heterocyclic organic compound and application thereof to OLED (organic light-emitting diode) device

An organic compound and multi-component technology, applied in the field of semiconductors, can solve the problems of efficiency roll-off, high exciton utilization rate, high fluorescence radiation efficiency, low S1 state radiation transition rate, etc., and achieve good photoelectric performance.

Active Publication Date: 2018-01-19
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 multi-element heterocyclic organic compound and application thereof to OLED (organic light-emitting diode) device
  • Boron-containing multi-element heterocyclic organic compound and application thereof to OLED (organic light-emitting diode) device
  • Boron-containing multi-element heterocyclic organic compound and application thereof to OLED (organic light-emitting diode) device

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Experimental program
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Effect test

Embodiment 1

[0063] The synthesis of embodiment 1 compound 5

[0064] The synthetic steps of compound are as follows:

[0065]

[0066]

[0067] Add 0.01mol 2,5-dibromofluorobenzene, 0.012mol M1, 0.02mol sodium carbonate and 10ml ethylene glycol dimethyl ether into a 50ml three-neck flask, pass through nitrogen protection, heat to 190 degrees Celsius, and stir for 48 hours. Then cool to room temperature, pour into a beaker, add 50ml of toluene and 50ml of water and stir for 20 minutes. After filtration, the filtrate was rotary evaporated and passed through a silica gel column to obtain a white intermediate 1a with a purity of 98.60% and a yield of 80.5%. HRMS(m / z): [M+H] + , the theoretical value is 523.06, and the measured value is 523.10.

[0068] In a 200ml three-necked flask, add 0.01mol of intermediate 1a and 50ml of diethyl ether, stir to dissolve, blow nitrogen, cool the system to -10°C, and slowly add 0.02mol of n-butyl lithium hexane solution dropwise under nitrogen atmos...

Embodiment 2

[0070] The synthesis of embodiment 2 compound 10

[0071] The synthetic steps of compound are as follows:

[0072]

[0073]

[0074] Add 0.01mol E1, 0.012mol M1, 0.02mol sodium carbonate and 10ml ethylene glycol dimethyl ether into a 50ml three-neck flask, pass through nitrogen protection, heat to 190 degrees Celsius, and stir for 48 hours. Then cool to room temperature, pour into a beaker, add 50ml of toluene and 50ml of water and stir for 20 minutes. After filtration, the filtrate was rotary evaporated and passed through a silica gel column to obtain the white intermediate 2a with a purity of 97.60% and a yield of 65.8%. HRMS(m / z): [M+H] + , the theoretical value is 573.11, and the measured value is 573.07.

[0075] In a 200ml three-necked flask, add 0.01mol of intermediate 2a and 50ml of diethyl ether, stir to dissolve, blow nitrogen, cool the system to -10°C, and slowly add 0.02mol of n-butyl lithium hexane solution dropwise under nitrogen atmosphere, and the addi...

Embodiment 3

[0077] The synthesis of embodiment 3 compound 20

[0078] The synthetic steps of compound are as follows:

[0079]

[0080]

[0081] Add 0.01mol 2,5-dibromofluorobenzene, 0.012mol M2, 0.02mol sodium carbonate and 10ml ethylene glycol dimethyl ether into a 50ml three-neck flask, pass through nitrogen protection, heat to 190 degrees Celsius, and stir for 48 hours. Then cool to room temperature, pour into a beaker, add 50ml of toluene and 50ml of water and stir for 20 minutes. After filtration, the filtrate was rotary evaporated and passed through a silica gel column to obtain a white intermediate 3a with a purity of 98.10% and a yield of 77.5%. HRMS(m / z): [M+H] + , the theoretical value is 496.89, and the measured value is 496.84.

[0082] In a 200ml three-necked flask, add 0.01mol of intermediate 3a and 50ml of diethyl ether, stir to dissolve, blow nitrogen gas, cool the system to -10°C, and slowly add 0.02mol of n-butyl lithium hexane solution dropwise under nitrogen at...

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Abstract

The invention discloses a boron-containing multi-element heterocyclic organic compound and an application thereof to an OLED (organic light-emitting diode) device. The compound utilizes benzo six-membered rings as a core, and boron is located on the six-membered ring in the center. The compound has the characteristics that molecules are not prone to crystallization and aggregation and film-formingproperty is good. When the compound is utilized as a luminous layer material of the OLED device, current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; besides, the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing polyheterocyclic organic compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide 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 application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both en...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
Inventor 叶中华李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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