Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices

An electroluminescence and compound technology, which is applied to boron-containing organic electroluminescence compounds and their application in organic electroluminescence devices, can solve the problem of efficiency roll-off, difficulty in high exciton utilization, high fluorescence radiation efficiency, low efficiency and low efficiency. state radiation transition rate and other issues, to achieve the effect of small energy level difference and avoid aggregation

Inactive Publication Date: 2020-07-31
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) T of the designed molecule 1 and S 1 states have strong CT features, very small S 1 -T 1 state energy gap, although a high T can be achieved by the TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to low S 1 Therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the quenching effect of T exciton concentration, most devices made of TADF materials Severe efficiency roll-off at high current densities

Method used

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  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices
  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices
  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0063] Preparation of Intermediate A

[0064] Preparation of Intermediate A-1:

[0065]

[0066] In a 250mL three-neck flask, under nitrogen protection, 0.02mol reactant D-1, 0.03mol reactant E-1, 0.05mol sodium tert-butoxide, 0.2mmol Pd 2 (dba) 3 1. Add 0.2mmol tri-tert-butylphosphine into 150mL toluene, stir and mix, heat to 110-120°C, reflux for 12-16 hours, take a sample and spot the plate, it shows that there is no reactant D-1 remaining, and the reaction is complete; naturally cool to room temperature , filtered, the filtrate was rotary evaporated under reduced pressure to no fraction, and passed through a neutral silica gel column to obtain intermediate F-1; ESI-MS (m / z) (M+): The theoretical value was 228.13, and the measured value was 227.16.

[0067] In a 250mL three-neck flask, under nitrogen protection, add 0.01mol intermediate F-1, 0.0005mol palladium acetate, 0.02mol PhCO 3 Bu-t, add 100mL dimethyl ether to dissolve, heat to 150°C under microwave, and react...

preparation Embodiment 1

[0120] Preparation Example 1: Synthesis of Compound 1:

[0121]

[0122] Add 10mmol of intermediate A-1 and 10mmol of intermediate B-1 into 75mL of toluene, reflux reaction at 45°C for 2h under stirring conditions, and remove the water and solvent in the reaction mixture by rotary evaporator, The residue was cooled to room temperature, and purified by column chromatography with dichloromethane and cyclohexane with a volume ratio of 1:3 to obtain the target intermediate C-1; ESI-MS (m / z) (M+): The theoretical value is 500.30, and the measured value is 500.14.

[0123] Add 10mmol of intermediate C-1 to 300mL of toluene, pass nitrogen gas into the reaction system for 30min, and add 0.15mmol of Pd respectively 2 (dba) 3 , 0.6mmol 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl and 20mmol t-BuONa, under the protection of nitrogen, reflux reaction at 80°C for 18h, after the reaction, the reaction mixture was filtered under reduced pressure, Take the filtrate, and carry out chr...

preparation Embodiment 2

[0125] Preparation Example 2: Synthesis of Compound 14:

[0126]

[0127] The preparation method of compound 14 is the same as in Example 1, except that intermediate A-1 is replaced by intermediate A-2, and intermediate B-1 is replaced by intermediate B-2; elemental analysis structure (molecular formula C 26 h 17 BF 2 N 2 O): theoretical value C, 73.96; H, 4.06; B, 2.56; N, 6.63; tested value: C, 73.94; H, 4.04; B, 2.52; N, 6.60. ESI-MS(m / z)(M + ): The theoretical value is 422.14, and the measured value is 422.10.

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Abstract

The invention discloses a boron-containing organic electroluminescent compound and an application thereof on organic electroluminescent devices, and belongs to the technical field of semiconductors. The boron-containing organic electroluminescent compound has a structure shown in a general formula (1). The invention also discloses an application of the boron-containing organic electroluminescent compound on organic electroluminescent devices. When the compound is used as a luminescent layer material of an organic electroluminescent device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, 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 organic electroluminescent compound 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 electrical excitation can be effectively used to e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1033C09K2211/1055C09K2211/104C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092H10K85/631H10K85/636H10K85/626H10K85/633H10K85/657H10K85/6572H10K85/6576H10K85/6574
Inventor 李崇谢丹丹叶中华张兆超王芳
Owner JIANGSU SUNERA TECH CO LTD
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