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Thermal activation delayed fluorescence material and application thereof

A technology of thermally activated delay and fluorescent materials, applied in the field of organic electroluminescent devices, can solve the problems of efficiency roll-off, severe, and insufficient stability of TADF materials, and achieve good photoelectric performance, good thermal stability and film-forming properties, The effect of novel structure

Active Publication Date: 2020-12-29
ZHEJIANG BAIKE SEMICON MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, compared with traditional fluorescent materials, the stability of TADF materials is insufficient, and the efficiency roll-off is severe. Therefore, it is necessary to develop thermally activated delayed fluorescent materials with high stability and high efficiency.

Method used

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  • Thermal activation delayed fluorescence material and application thereof
  • Thermal activation delayed fluorescence material and application thereof
  • Thermal activation delayed fluorescence material and application thereof

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0045] The preparation of embodiment intermediate

[0046]

[0047] 1. Synthesis of Intermediate I

[0048] In the flask, add 5,8-dibromo-2,3-diphenylquinoxaline (10g, 22.7mmol), carbazole (3.4g, 20.3mmol), sodium tert-butoxide (3.3g, 34.3mmol), PD 2 (dba) 3 (0.15g), tri-tert-butylphosphine (0.1g) and 100mL anhydrous toluene, reflux reaction for 2 hours, add dilute hydrochloric acid to adjust to weakly acidic liquid separation, dry, concentrate, and the crude product is recrystallized from toluene to obtain 7.2g, the yield 60%. 1 H NMR (400MHz, CDCl 3)δ: 8.11-8.14(m, 2H), 8.04(d, J=7.2Hz, 1H), 7.82(d, J=7.6Hz, 1H), 7.61-7.63(m, 2H), 7.50-7.57(m ,4H),7.32-7.38(m,8H),7.20-7.24(m,2H).HRMS(ESI,m / z):[M+H] + 526.10.

[0049] 2. Synthesis of Intermediate II

[0050] In the flask, add intermediate I (7g, 13.3mmol), pinacolate (4.1g, 16.1mmol), potassium acetate (3.9g, 39.7mmol), Pd (PPh 3 ) 3 Cl 2 (0.07g), 70mL of anhydrous toluene, reflux reaction for 5 hours, cooled, p...

Embodiment 1

[0056] The synthesis of embodiment 1 compound 1

[0057]

[0058] Intermediate II (2.0g, 3.49mmol), 1,4-dibromobenzene (0.40g, 1.70mmol), potassium carbonate (0.70g, 5.09mmol), Pd(PPh 3 ) 4 (0.01g), then add toluene (10mL), ethanol (5mL) and deionized water (5mL), reflux reaction under nitrogen protection for 5 hours, liquid separation, concentration, crude product obtains 1.4g white product through column chromatography, productive rate is 86%. 1 HNMR (400MHz, CDCl 3 )δ: 8.11-8.14(m, 4H), 7.93(d, J=6.4Hz, 2H), 7.79(d, J=6.4Hz, 2H), 7.53-7.59(m, 12H), 7.47-7.49(m ,4H),7.30-7.37(m,16H),7.19-7.24(m,4H).HRMS(ESI,m / z):[M+H] + 969.35.

Embodiment 2

[0059] The synthesis of embodiment 2 compound 9

[0060]

[0061] Intermediate II (2g, 3.49mmol), 2,5-dibromopyridine (0.40g, 1.69mmol), potassium carbonate (0.70g, 5.06mmol), Pd(PPh 3 ) 4 (0.01g), then add toluene (10mL), ethanol (5mL) and deionized water (5mL), reflux reaction under nitrogen protection for 5 hours, liquid separation, concentration, crude product obtains 1.3g white product through column chromatography, productive rate is 80%. 1 HNMR (400MHz, CDCl 3 )δ: 9.43(d, J=2.0Hz, 1H), 8.07-8.14(m, 6H), 7.94(d, J=6.8Hz, 1H), 7.80-7.88(m, 3H), 7.54-7.59(m ,8H),7.47-7.49(m,4H),7.30-7.37(m,16H),7.19-7.24(m,4H).HRMS(ESI,m / z):[M+H] + 970.35.

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Abstract

The invention belongs to the technical field of organic electroluminescent devices, and particularly relates to a thermal activation delayed fluorescence material and application thereof. According tothe invention, the thermal activation delayed fluorescence material provided by the invention has a double quinoxaline structure, is novel in structure and good in photoelectric properties, and is suitable for being used as a luminescent material of an organic electroluminescent device, and the organic electroluminescent device prepared from the luminescent material has high device efficiency andlong service life; and the thermal activation delayed fluorescence material has very good thermal stability and film-forming property, and the glass-transition temperature is as high as 215 DEG C, sothat the thermal activation delayed fluorescence material has good thermal stability.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent devices, in particular to a thermally activated delayed fluorescent material and its application. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, The light-emitting layer and the electron-transport layer, the holes generated by the anode are combined with the electrons generated by the cathode through the hole-transport layer to form excitons in the light-emitting layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as required. [0003] As a new type of display technology, organic electroluminescent devices have self-illuminat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D519/00C07D413/14C07D241/42C07D401/14C07D417/14C09K11/06H01L51/50H01L51/54
CPCC07D403/14C07D519/00C07D413/14C07D241/42C07D401/14C07D417/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1033C09K2211/1037H10K85/636H10K85/654H10K85/6572H10K85/657H10K50/11
Inventor 王郁生周海涛
Owner ZHEJIANG BAIKE SEMICON MATERIALS CO LTD