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Carbazole thermal activation delayed fluorescence material and preparation method thereof

A technology of thermally activated delay and fluorescent materials, applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc.

Inactive Publication Date: 2020-05-05
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the design of synthetic novel TADF molecules remains a great challenge.

Method used

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  • Carbazole thermal activation delayed fluorescence material and preparation method thereof
  • Carbazole thermal activation delayed fluorescence material and preparation method thereof
  • Carbazole thermal activation delayed fluorescence material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 The preparation method of compound I-1 and I-3

[0037] 1) Weigh 2.0g of carbazole, 3.6g of 2,3,5,6-tetrafluoro-4-iodobenzonitrile and 1.6g of potassium tert-butoxide after being dissolved in 50mL of dimethylformamide and added to the there-necked flask , the temperature rose to 100 degrees, and the reaction time was 4 hours. After the reaction was completed, the temperature was lowered to room temperature, filtered, and the organic solvent was distilled under reduced pressure, and the solid generated by adding 20 ml of ethyl acetate was filtered and washed to obtain I-3 compound 3.6g , the yield is 89%.

[0038] The detection parameters are as follows:

[0039] 1 H-NMR: 6.65-6.48 (m, 3H), 6.80-6.73 (m, 2H), 7.30-7.23 (m, 2H), 7.41-7.31 (m, 4H), 7.52-7.45 (m, 6H), 7.60 -7.58(m, 2H), 7.66-7.64(m, 2H), 7.73-7.71(m, 2H), 8.05-8.03(m, 1H), 18.10(s, 1H), 8.31(s, 1H).

[0040] 19 F-NMR: -130.60, -138.25.

[0041] 2) after weighing 3.0g I-3 and 6.2g 4,4'-dip...

Embodiment 2

[0047] Embodiment 2 The preparation method of compound I-2 and I-4

[0048] 1) Weigh 2.0g 2',4',6'-trifluoro-[1,1':3',1"-terphenyl]-5'-carbonitrile and dissolve 1.2g carbazole in 80mL dimethyl After the formyl, added to the there-necked flask, slowly adding 0.3g (60%) of sodium hydride, the temperature was raised to 100 degrees and reacted for 14 hours, after the reaction was completed, the temperature was lowered to room temperature, and the organic solvent was distilled under reduced pressure after the reaction was completed, Add 100 mL of ice water, filter the resulting solid, add 100 mL of methanol to the obtained solid, filter, add 100 mL of ethyl acetate to the obtained solid, filter, and dry to obtain 2.1 g of compound I-4 with a yield of 72%.

[0049] The detection parameters are as follows:

[0050] 1 H-NMR: 7.18-7.13 (m, 1H), 7.42-7.40 (m, 1H), 7.53-7.49 (m, 1H), 8.18-8.15 (d, J=8.17 Hz, 1H).

[0051] 19 F-NMR: -113.35.

[0052] 2) after weighing 2.0g I-4 and 3....

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Abstract

The invention discloses a carbazole thermal activation delayed fluorescence material and a preparation method thereof, and belongs to the technical field of organic electroluminescence display. The structure of the fluorescent material is shown as a formula I-1-4, and the thermal activation delayed fluorescent material provided by the invention has structural uniqueness and novelty, and has important application value for researching and developing a three-high thermal activation delayed fluorescent material with high luminous efficiency, high thermal stability, high color purity and the likein the future.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and relates to the preparation of a carbazole-based thermally activated delayed fluorescent material. Background technique [0002] In recent years, in the field of organic light-emitting diodes (OLEDs), thermally activated delayed fluorescence (TADF) emitters have received worldwide attention due to their ability to achieve nearly 100% internal quantum efficiency (IQE) through an efficient intersystem reverse crossover (RISC) process. extensive attention within. Compared with phosphorescent complexes, TADF materials have obvious resource advantages and lower costs. [0003] Since organic materials with thermally activated delayed fluorescence (TADF) were successfully synthesized, TADF materials have attracted great attention from many scientific research institutions and companies at home and abroad. The energy level difference between the singlet state and the trip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
CPCC07D209/86C09K11/06C09K2211/1029
Inventor 金国范
Owner JIANGSU UNIV