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Boron-containing six-membered heterocyclic derivative and application thereof to organic light-emitting device

A technology of six-membered heterocycles and derivatives, which can be used in electrical solid devices, compounds containing elements of Group 3/13 of the periodic table, electrical components, etc. Excitons utilization and high fluorescence radiation efficiency to achieve the effect of good optoelectronic performance

Inactive Publication Date: 2019-04-05
VALIANT 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 six-membered heterocyclic derivative and application thereof to organic light-emitting device
  • Boron-containing six-membered heterocyclic derivative and application thereof to organic light-emitting device
  • Boron-containing six-membered heterocyclic derivative and application thereof to organic light-emitting device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthesis of embodiment 1 compound 5

[0057] The synthetic steps of compound are as follows:

[0058]

[0059] In a 150ml four-neck flask, add 0.01mol of A1 and 50ml of tetrahydrofuran, protect it with nitrogen, cool to -78 degrees Celsius, and then slowly drop in 0.02mol of n-butyl lithium cyclohexane solution. After the drop is completed, stir for 3 hours. Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for reaction for 1 hour, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B1, purity 98.2%, yield 90%. HRMS(m / z): [M+H] + , the theoretical value is 417.14, and the measured value is 417.11.

[0060] Add 50ml of toluene and 0.01mol B1 to a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, and then slowly drop in a t...

Embodiment 2

[0063] The synthesis of embodiment 2 compound 10

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

[0065]

[0066] 150ml four-neck flask, add 0.01mol of A2 and 50ml of tetrahydrofuran, nitrogen protection, cool to -78 degrees Celsius, then slowly drop into 0.02mol of n-butyllithium cyclohexane solution, after the completion of the drop, stir the reaction for 3 hours, Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for 1 hour reaction, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B2 with a purity of 98.4% and a yield of 87.5%. HRMS(m / z): [M+H] + , the theoretical value is 467.20, and the measured value is 467.15.

[0067] Add 50ml of toluene and 0.01mol B2 to a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, and th...

Embodiment 3

[0070] The synthesis of embodiment 3 compound 20

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

[0072]

[0073] Add 0.01mol of A3 and 50ml of tetrahydrofuran into a 150ml four-necked flask, protect it with nitrogen, cool to -78 degrees Celsius, then slowly drop in 0.02mol of n-butyllithium cyclohexane solution, and stir for 3 hours to react. Raise the temperature to -10 degrees Celsius, drop in 0.01mol dimethyl tin dichloride tetrahydrofuran solution, after the dropwise addition, keep the temperature for 1 hour reaction, then warm up to room temperature, remove the tetrahydrofuran by rotary evaporation, and then rinse twice with ethanol to obtain Pale yellow solid B3 with a purity of 97.6% and a yield of 87.5%. HRMS(m / z): [M+H] + , the theoretical value is 391.06, and the measured value is 391.12.

[0074]Add 50ml of toluene and 0.01mol B3 into a 150ml three-necked flask, protect it with nitrogen, cool down to -78 degrees Celsius, and then slowly drop in a to...

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Abstract

The invention discloses a boron-containing six-membered heterocyclic derivative and an application thereof to an organic light-emitting device. The derivative takes a benzo five-membered ring as a core, boron is positioned at the center five-membered ring, and the derivative has the advantages that molecules are not easily crystallized or gathered, and the derivative has a good film-forming property. When the derivative is used as a luminous layer material of the organic light-emitting device, the current efficiency, the power efficiency and the external quantum efficiency of the device can begreatly improved, and 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 six-membered heterocyclic derivative 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F5/02C09K2211/1007C09K2211/1096C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 叶中华张兆超李崇张小庆
Owner VALIANT CO LTD
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