Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound

A compound, 10-technology, applied in the application field of light-emitting layer materials in organic light-emitting diodes, can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc., to achieve Reduce efficiency roll-off, good industrialization prospects, improve the effect of high exciton utilization and high fluorescence radiation efficiency

Active Publication Date: 2017-08-18
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although theoretically TADF materials can achieve 100% exciton utilization, 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 High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 sta

Method used

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  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound
  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound
  • Compound taking 10,10-diaryl substituted anthranone as mother nucleus and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0046] Example 1 Synthesis of raw material A

[0047]

[0048] In a 1L three-necked flask, add 19.8g phenol (0.21mol), 20.8g anthraquinone (0.10mol), 0.2g mercaptopropionic acid, 400mL dichloroethane, mix and stir, heat up to 60~65℃ dropwise add 3.0g methyl After the addition of sulfonic acid, the reaction was kept at 60~65℃ for 4 hours; after the reaction, the temperature was lowered and the liquid was separated, and the solvent was removed from the organic phase under reduced pressure to obtain the crude product, which was recrystallized with absolute ethanol and obtained by column chromatography. White crystals-compound X, HPLC purity 99.5%, yield 46.58%;

[0049] Add 18.9g compound X (0.05mol) and 100g pyridine in a 500mL three-necked flask, add 33.8g trifluoromethanesulfonic anhydride (0.12mol) dropwise to 0~5℃, and react at room temperature for 6 hours; then add water to quench and extract The solvent was removed from the organic phase under reduced pressure, and the column ...

Example Embodiment

[0052] Example 2 Synthesis of raw material B

[0053]

[0054] In a 250ml three-neck flask, under the protection of nitrogen, add 6.42g raw material A (0.01mol), 10.16g diboronic acid pinacol ester (0.04mol), 4.90g potassium acetate (0.05mol), 0.30g pd2(dba)3 , 0.20g tri-tert-butylphosphorus, 100ml toluene, reflux for 20 hours; after the reaction, cooling, filtering, rotary evaporation of the filtrate, column chromatography to obtain raw material B, HPLC purity 99.8%, yield 88.26%;

[0055] High resolution mass spectrometry ESI source, positive ion mode, molecular formula C38H40B2O5, theoretical value: 598.3062, test value: 598.3066.

[0056] Elemental analysis (C38H40B2O5): theoretical value C: 76.28, H: 6.74, O: 13.37, test value C: 76.26, H: 6.75, O: 13.40.

Example Embodiment

[0057] Example 3 Synthesis of Compound 1

[0058] synthetic route:

[0059]

[0060] In a 250ml three-neck flask, under the protection of nitrogen, add 3.21g raw material A (0.005mol), 2.20g compound M01 (0.012mol), 1.44g sodium tert-butoxide (0.015mol), 0.15g pd2(dba)3, 0.10g Tri-tert-butyl phosphorus, 100ml of toluene, reflux for 20 hours; after the reaction, cooling, filtering, rotary evaporation of the filtrate, column chromatography to obtain compound 1, HPLC purity 99.9%, yield 78.40%;

[0061] High resolution mass spectrometry ESI source, positive ion mode, molecular formula C50H32N2O3, theoretical value: 708.2413, test value: 708.2411.

[0062] Elemental analysis (C50H32N2O3): theoretical value C: 84.73, H: 4.55, N: 3.95, O: 6.77, test value C: 84.71, H: 4.55, N: 3.98, O: 6.76.

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Abstract

The invention discloses a compound taking 10,10-diaryl substituted anthranone as a mother nucleus and application of the compound to an organic electroluminescent device. The compound takes 10,10-diaryl substituted anthranone as the mother nucleus, and therefore has the characteristics that the probabilities of crystallization and clustering between molecules are low and the film-forming property is favorable. When the compound serves as a luminescent layer material of an OLED luminescent device, the manufactured OLED device has favorable photoelectric property.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to a compound with 10,10-diaryl substituted anthrone as the core and its application as a light-emitting layer material in an organic light-emitting diode. 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 electrode...

Claims

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Application Information

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IPC IPC(8): C07D265/38C07D279/22C07D219/02C07D209/86C07D209/80C07D519/00C07D241/46C07D221/18C07D265/34C07D241/38C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/80C07D209/86C07D219/02C07D221/18C07D241/38C07D241/46C07D265/34C07D265/38C07D279/22C07D519/00C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1088C09K2211/1092H10K85/615H10K85/6572H10K85/657H10K50/00
Inventor 高自良张婷婷石宇张司南
Owner JIANGSU SUNERA TECH CO LTD
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