Organic compound, thermally-activated delayed fluorescence material and application of organic compound

An organic compound and selected technology, applied in the field of organic compounds and thermally activated delayed fluorescent materials, can solve the problems that the performance is difficult to meet high-performance OLED devices, less TADF materials, etc., to improve carrier balance, improve transmission capacity, and improve The effect of device efficiency

Active Publication Date: 2020-08-25
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] At present, CN109535159A, CN109575059A and CN111116620A and other prior art disclose TADF materials and their applications, but there are few TADF materials found so far, and its performance is difficult to meet people's requirements for high-performance OLED devices. There is a lot of room for improvement in many aspects such as performance and preparation process

Method used

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  • Organic compound, thermally-activated delayed fluorescence material and application of organic compound
  • Organic compound, thermally-activated delayed fluorescence material and application of organic compound
  • Organic compound, thermally-activated delayed fluorescence material and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] This embodiment provides an organic compound with the following structure:

[0108]

[0109] The preparation method of this organic compound M1 is:

[0110]

[0111] Add compound 1A (5.36g, 20mmol), compound 1B (11.24g, 40mmol), 150mL of toluene, cesium carbonate (13.03g, 40mmol) and tetrakis(triphenylphosphine) palladium to a 250mL three-necked flask. Pd(PPh 3 ) 4 (0.23g, 0.2mmol) and tri-tert-butylphosphine P(t-Bu) 3 (40.5mg, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. After being cooled to room temperature, the reaction solution was poured into 200 mL of ice water, extracted three times with dichloromethane, the organic phases were combined, and the solvent was removed by rotary evaporation, and silica gel column chromatography (the eluent was a mixture of dichloromethane / n-hexane with a volume ratio of 1:1) solution) separation and purification to obtain the target product M1.

[0112] The characterization results of the organic...

Embodiment 2

[0116] This embodiment provides an organic compound with the following structure:

[0117]

[0118] The preparation method of this organic compound M2 is:

[0119]

[0120] Add compound 1A (5.36g, 20mmol), compound 2B (5.62g, 20mmol), compound 2C (5.41g, 20mmol), 150mL toluene and cesium carbonate (13.03g, 40mmol) in a 250mL three-necked flask , Pd(PPh 3 ) 4 (0.23g, 0.2mmol) and P(t-Bu) 3 (40.5mg, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. Cooled to room temperature, the reaction solution was poured into 200mL of ice water, extracted three times with dichloromethane, the organic phases were combined, and the solvent was removed by rotary evaporation, and silica gel column chromatography (the eluent was a mixture of dichloromethane / n-hexane with a volume ratio of 1:1) solution) separation and purification to obtain the target product M2.

[0121] The characterization results of the organic compound M2:

[0122] 1 H-NMR (400MHz, CDCl 3 ): ...

Embodiment 3

[0125] This embodiment provides an organic compound with the following structure:

[0126]

[0127] The preparation method of this organic compound M3 is:

[0128]

[0129] Add compound 1A (5.36g, 20mmol), compound 3B (7.84g, 20mmol), compound 3C (5.24g, 20mmol), 150mL toluene and cesium carbonate (13.03g, 40mmol) in a 250mL three-necked flask , Pd(PPh 3 ) 4 (0.23g, 0.2mmol) and P(t-Bu) 3 (40.5mg, 0.2mmol), and then reacted at 120°C for 24h under nitrogen atmosphere. Cooled to room temperature, the reaction solution was poured into 200mL of ice water, extracted three times with dichloromethane, the organic phases were combined, and the solvent was removed by rotary evaporation, and silica gel column chromatography (the eluent was a mixture of dichloromethane / n-hexane with a volume ratio of 1:1) solution) separation and purification to obtain the target product M3.

[0130] The characterization result of the organic compound M3:

[0131] 1 H-NMR (400MHz, CDCl 3 ):...

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Abstract

The invention provides an organic compound, a thermally-activated delayed fluorescence material and application of the organic compound. The organic compound has a structure as shown in a formula I and is a novel nitrogen-containing heterocyclic organic small-molecular compound, and aggregation of the compound and formation of pi aggregation or exciplex due to direct accumulation of a conjugate plane are avoided through design of a parent nucleus structure and introduction of a large steric hindrance group, so luminous efficiency is improved. The organic compound has TADF characteristics, andcan be used as a light-emitting layer material of an OLED device to improve the transmission capability of two carriers, improve carrier balance, enhance the fluorescence quantum efficiency of the device and reduce the voltage of the device; and substituent groups are selected and designed, and the compound realizes full-wave spectrum emission when used as a light-emitting layer doping material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, a thermally activated delayed fluorescent material and applications thereof. Background technique [0002] Organic Light Emitting Display (OLED) device is a new type of display technology. The device has a sandwich-like structure, including an anode, a cathode, and an organic layer sandwiched between the cathode and anode. When a voltage is applied to the electrodes of the device , Charges migrate and recombine in the organic layer under the action of an electric field to emit light. Compared with traditional liquid crystal display technology, OLED has the advantages of high efficiency, fast response, low energy consumption, low driving voltage, light and thin, wide viewing angle, continuously adjustable luminous color, simple production process and flexible display, etc., and has been widely used in Industries such a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07D519/00C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07D487/22C07D519/00C07F9/65616C09K11/06C09K2211/1011C09K2211/1074C09K2211/1059C09K2211/1037C09K2211/1044C09K2211/1066C09K2211/1014C09K2211/1088C09K2211/1077H10K85/653H10K85/654H10K85/657H10K85/6572H10K50/12
Inventor 汪奎李侠周慧芳
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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