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An organic electroluminescent device based on 10,10-diaryl anthrone compound and its application

An electroluminescent device, diaryl anthrone technology, applied in the field of semiconductors, can solve difficult problems such as high exciton utilization rate and high fluorescence radiation efficiency, low S1 state radiation transition rate, efficiency roll-off, etc.

Active Publication Date: 2018-12-28
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) The T1 and S1 states of the designed molecule have strong CT features and a very small S1-T1 state energy gap, although high T can be achieved by the TADF process 1 →S 1 State exciton conversion rate, but at the same time lead to low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization rate and high fluorescence radiation efficiency;
[0007] (2) Even if doped devices have been used to alleviate the T-exciton concentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • An organic electroluminescent device based on 10,10-diaryl anthrone compound and its application
  • An organic electroluminescent device based on 10,10-diaryl anthrone compound and its application
  • An organic electroluminescent device based on 10,10-diaryl anthrone compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of Example 1 Raw Material A

[0068]

[0069] 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 ℃ and add dropwise 3.0g methyl alcohol The sulfonic acid was added dropwise, and the reaction was incubated for 4 hours at 60 to 65 ° C; after the reaction was completed, the temperature was cooled, washed with water, and the organic phase was decompressed to remove the solvent to obtain a crude product, which was recrystallized with absolute ethanol and obtained by column chromatography. White crystal - compound X, HPLC purity 99.5%, yield 46.58%;

[0070] 18.9g of compound X (0.05mol) and 100g of pyridine were added to a 500mL three-necked flask, the temperature was lowered to 0~5°C and 33.8g of trifluoromethanesulfonic anhydride (0.12mol) was added dropwise, and the reaction was carried out at room temperature for 6 hours; The solvent was rem...

Embodiment 2

[0073] The synthesis of embodiment 2 raw material B

[0074]

[0075] In a 250ml three-necked flask, under nitrogen protection, add 6.42g raw material A (0.01mol), 10.16g bis-borate pinacol ester (0.04mol), 4.90g potassium acetate (0.05mol), 0.30g pd2(dba)3 , 0.20g tri-tert-butylphosphorus, 100ml toluene, refluxed 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%;

[0076] High resolution mass spectrometry ESI source, positive ion mode, molecular formula C38H40B2O5, theoretical value: 598.3062, tested value: 598.3066.

[0077] Elemental analysis (C38H40B2O5): Theoretical C: 76.28, H: 6.74, O: 13.37, Tested C: 76.26, H: 6.75, O: 13.40.

Embodiment 3

[0078] Example 3 Synthesis of Compound 1

[0079] synthetic route:

[0080]

[0081] In a 250ml three-necked flask, under nitrogen protection, 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-butylphosphorus, 100 ml of toluene, refluxed for 20 hours; after the reaction, cooling, filtration, rotary evaporation of the filtrate, and column chromatography to obtain compound 1, HPLC purity 99.9%, yield 78.40%;

[0082] High resolution mass spectrometry ESI source, positive ion mode, molecular formula C50H32N2O3, theoretical value: 708.2413, test value: 708.2411.

[0083] Elemental analysis (C50H32N2O3): Theoretical C: 84.73, H: 4.55, N: 3.95, O: 6.77, Tested C: 84.71, H: 4.55, N: 3.98, O: 6.76.

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Abstract

The invention discloses an organic electroluminescent device containing 10,10-diaryl anthrone compound and its application. The device comprises a hole transport layer, a light emitting layer and an electron transport layer. The material of the light emitting layer of the device contains 10 , 10-diaryl anthrone as the core group of the compound, the structural formula of the compound is shown in the general formula (1). The material with 10,10-diaryl anthrone as the core group in the present invention has a small triplet and singlet energy difference, so it is easy to realize the energy transfer between the host and guest materials, so that the energy that is originally lost in the form of heat The energy is easy to use, so it is easier to obtain high efficiency of the device, and further, when the dopant material is selected as a fluorescent material, it is easier to obtain the luminescent radiation of the dopant material, so it is easier to obtain the long life of the material.

Description

technical field [0001] The present invention relates to the technical field of semiconductors, in particular to an organic electroluminescence device in which the material of the light-emitting layer is a compound with 10,10-diarylanthrone as the core and an application thereof. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products. [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 purpose to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, the positive and negative charges in the functional material film layer of the organic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/50H01L51/54C07D265/38C07D279/22C07D219/02C07D209/86C07D209/80C07D519/00C07D221/18C07D265/34C07D241/38
CPCC07D209/80C07D209/86C07D219/02C07D221/18C07D241/38C07D265/34C07D265/38C07D279/22C07D519/00H10K85/6572H10K85/657H10K50/11
Inventor 李崇张兆超王立春
Owner VALIANT CO LTD
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