Organic compound with diboron as core, preparation method of organic compound and application of organic compound to organic light-emitting device

An organic compound and compound technology, which is applied in the fields of silicon-organic compounds, compounds containing Group 3/13 elements of the periodic table, and organic chemistry, etc. Transition rate, efficiency roll-off, etc.

Inactive Publication Date: 2020-07-07
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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 T1 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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  • Organic compound with diboron as core, preparation method of organic compound and application of organic compound to organic light-emitting device
  • Organic compound with diboron as core, preparation method of organic compound and application of organic compound to organic light-emitting device
  • Organic compound with diboron as core, preparation method of organic compound and application of organic compound to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0140] Preparation of Compound 4

[0141]

[0142] 1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.005mol of raw material 1 and 0.005mol of raw material 2, 0.015mol of tert-butyllithium, and 150ml of tert-butylbenzene, stir and mix, heat to 60°C, and stir for 2 hours; Then cool naturally to room temperature, dropwise add 0.015mol BBr 3 and 0.1mol diisopropylethylamine, stirred and reacted at room temperature for 1 hour, sampling and pointing the plate, showing that there was no raw material 1 remaining, and the reaction was complete; adding water and dichloromethane for extraction and liquid separation; taking the organic phase, adding anhydrous magnesium sulfate Remove water, filter, and the filtrate is subjected to decompression rotary evaporation (-0.09MPa, 25°C), and passes through a neutral silica gel column to obtain intermediate 1 with a HPLC purity of 99.5% and a yield of 65.7%; elemental analysis structure (molecular formula C 36 h 32 B ...

preparation Embodiment 2

[0145] Preparation of Compound 22

[0146]

[0147] Repeat the preparation process of Preparation Example 1, the difference is that raw material 4 is used instead of raw material 1, raw material 5 is used instead of raw material 2, intermediate 3 is prepared, intermediate 4 is obtained after bromination, intermediate 4 and raw material 6 are used for coupling reaction , the target compound 22 was obtained with a purity of 99.6% and a yield of 71.3%. Elemental analysis structure (molecular formula C 49 h 39 B 2 NO): theoretical value C, 86.62; H, 5.79; B, 3.18; N, 2.06; ESI-MS(m / z)(M + ): The theoretical value is 679.32, and the measured value is 679.71.

preparation Embodiment 3

[0148] Preparation of Compound 46

[0149]

[0150] Repeat the preparation process of Preparation Example 1, the difference is that raw material 7 is used instead of raw material 1, raw material 8 is used instead of raw material 2, intermediate 5 is prepared, intermediate 6 is obtained after bromination, intermediate 6 and raw material 9 are used for coupling reaction , the target compound 46 was obtained with a purity of 99.5% and a yield of 73.7%. Elemental analysis structure (molecular formula C 50 h 32 B 2 N 2 ): theoretical value C, 88.00; H, 4.73; B, 3.17; N, 4.10; test value: C, 88.01; H, 4.71; B, 3.15; N, 4.13. ESI-MS(m / z)(M + ): The theoretical value is 682.28, and the measured value is 682.55.

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Abstract

The invention relates to an organic compound taking diboron as a core, a preparation method of the organic compound and application of the organic compound to an organic light-emitting device. The structure of the compound is shown as a general formula (1); the whole molecule of the organic compound with diboron as the core is of a large rigid structure, the introduction of branched chains reducesthe planarity of the material, the steric hindrance of the material is increased, the material is not easy to rotate, and the three-dimensional space structure is more stable, so that the compound has high glass transition temperature and molecular thermal stability; in addition, HOMO and LUMO distribution positions of the compound are separated from each other, so that 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 semiconductor materials, in particular to an organic compound containing two boron atoms in its structure, its preparation method and its application in organic electroluminescent devices. Background technique [0002] The application of organic light-emitting diodes (OLEDs) in large-area flat-panel displays and lighting has attracted extensive attention from both industry and academia. However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit coupling at the center of heavy atoms, the singlet and triplet excitons formed by electric...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1007C09K2211/1011C09K2211/1096C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1033H10K85/622H10K85/623H10K85/636H10K85/633H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40
Inventor 唐丹丹李崇张兆超王芳
Owner JIANGSU SUNERA TECH CO LTD
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