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

A technology of organic compounds and compounds, applied in silicon organic compounds, compounds containing elements of group 3/13 of the periodic table, organic chemistry, etc., can solve the problems of efficiency roll-off, difficult high exciton utilization rate and high fluorescence radiation efficiency, Low S1 state radiative transition rate and other issues

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...

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

[0062] Embodiment 1: the synthesis of compound 4:

[0063]

[0064] (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 molPd 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 98.7% and a yield of 60.2%;

[0065] (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 cool to room temperature, dr...

Embodiment 2

[0068] Embodiment 2: the synthesis of compound 15:

[0069]

[0070] The preparation method of intermediate 2 is the same as that of intermediate 1 in Example 1, except that raw material 3 is used to replace raw material 1, and raw material 4 is used to replace raw material 2.

[0071] (3) Add 0.01mol of intermediate 2 into a 250mL three-necked flask, add 150mL of dichloromethane to dissolve it, stir at room temperature (25°C), add 0.03mol of NBS (N-bromosuccinimide) in batches, The reaction was observed by thin layer chromatography (TLC) until complete. The reaction mixture was poured into 200 mL of water and stirred for 2 h, extracted with dichloromethane, and separated; the organic phase was taken, added anhydrous magnesium sulfate to remove water, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09 MPa, 25 ° C), and the Neutral silica gel column to obtain intermediate II-1, HPLC purity 98.0%, yield 68.9%.

[0072] (4) Under a nitrogen atmosp...

Embodiment 3

[0074] Embodiment 3: the synthesis of compound 25:

[0075]

[0076] The preparation method of compound 25 is the same as in Example 2, except that raw material 3 is replaced by raw material 7, raw material 4 is replaced by raw material 6, and raw material 5 is replaced by raw material 39.

[0077] Elemental analysis structure (molecular formula C 69 h 70 BN 3 o 2 ): Theoretical value: C, 84.21; H, 7.17; B, 1.10; N, 4.27; O, 3.25; Test value: C, 84.20; ESI-MS(m / z)(M + ): The theoretical value is 984.15, and the measured value is 984.17.

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Abstract

The invention relates to a boron-containing organic compound and application of the boron-containing organic compound to an OLED device. The structure of the compound is shown as a general formula (1), the whole molecule of the compound is a large rigid structure, and the introduction of substituent groups reduces the planarity of a material, so the steric hindrance of the material is increased, the material is not easy to rotate, and a three-dimensional space structure is more stable; and therefore, the compound has higher glass transition temperature and 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; and 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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IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1007C09K2211/1029C09K2211/104C09K2211/1096C09K2211/1037C09K2211/1044H10K85/657H10K85/40H10K50/11
Inventor 吴秀芹唐丹丹李崇王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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