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

An organic compound and general formula technology, applied to organic compounds and their application in organic electroluminescent devices, can solve difficult and high exciton utilization and high fluorescence radiation efficiency, efficiency roll-off, and low S1 state radiation transition speed etc.

Inactive Publication Date: 2020-08-25
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although TADF materials can achieve 100% exciton utilization in theory, 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 compound and application thereof in organic electroluminescent device
  • Boron-containing organic compound and application thereof in organic electroluminescent device
  • Boron-containing organic compound and application thereof in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Embodiment 1: the synthesis of compound H2:

[0069]

[0070] (1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of raw material 1, 0.012mol of raw material 2, and 150ml of toluene, stir and mix, then add 0.02mol of sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampling plate, showed that there was no raw material 1 remaining, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column to obtain intermediate I-1, with a HPLC purity of 98.4% and a yield of 65.2%;

[0071] (2) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate I-1, 0.012mol of tert-butyllithium, and 150ml of tert-butylbenzene, stir and mix, heat to 60°C, and stir for 2 hours; then Naturally cooled to room temperature...

Embodiment 2

[0075] Embodiment 2: the synthesis of compound H12:

[0076]

[0077] The preparation method of compound H12 is the same as in Example 1, except that raw material 4 is used to replace raw material 1, raw material 5 is used to replace raw material 2, and raw material 6 is used to replace raw material 3. Elemental analysis structure (molecular formula C 78 h 48 BN 3 o 2 ): theoretical value C, 87.55; H, 4.52; B, 1.01; N, 3.93; 0, 2.99; test value C, 87.53; ESI-MS(m / z)(M + ): The theoretical value is 1070.07, and the measured value is 1070.10.

Embodiment 3

[0078] Embodiment 3: the synthesis of compound H20:

[0079]

[0080] The preparation method of compound H20 is the same as in Example 1, except that raw material 1 is replaced by raw material 7, raw material 2 is replaced by raw material 8, and raw material 3 is replaced by raw material 9.

[0081] Elemental analysis structure (molecular formula C 90 h 60 B 4 N 4 ): theoretical value: C, 87.12; H, 4.87; B, 3.49; N, 4.52; test value: C, 87.12; H, 4.88; B, 3.50; N, 4.50. ESI-MS(m / z)(M + ): The theoretical value is 1240.74, and the measured value is 1240.70.

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Abstract

The invention relates to a boron-containing organic compound and application thereof to an organic light-emitting device, belonging to the technical field of semiconductors. The structure of the boron-containing organic compound is shown as a general formula (1). The invention also discloses the application of the boron-containing organic compound in an organic electroluminescent device. Accordingto the boron-containing organic compound, the whole molecule of the compound is of a large rigid structure, the planarity of a material is reduced through introduction of substituent groups, the steric hindrance of the material is increased, the material is not prone to rotation, a three-dimensional space structure is more stable, and therefore, the compound has high glass transition temperatureand molecular thermal stability; in addition, the HOMO and LUMO distribution positions of the compound are separated from each other, so the compound has appropriate HOMO and LUMO energy levels. Therefore, after the compound is applied to the OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing organic compound and its application in organic electroluminescent devices. 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 ends of the OLED light-emitting device, and the pos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/104C09K2211/1088C09K2211/1096C09K2211/1092C09K2211/1044H10K85/623H10K85/622H10K85/636H10K85/633H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor 吴秀芹唐丹丹李崇王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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