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Organic light emission diode device containing 10, 10-diaryl anthrone compound and application thereof

An electroluminescent device, a technology of diaryl anthrone, applied in the direction of electric solid state devices, electrical components, organic chemistry, etc., can solve the problems of efficiency roll-off, low S1 state radiative transition rate, difficult high exciton utilization rate and high Fluorescent radiation efficiency and other issues

Active Publication Date: 2017-08-18
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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  • Organic light emission diode device containing 10, 10-diaryl anthrone compound and application thereof
  • Organic light emission diode device containing 10, 10-diaryl anthrone compound and application thereof
  • Organic light emission diode device containing 10, 10-diaryl anthrone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Synthesis of 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℃ dropwise add 3.0g methylbenzene 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%;

[0070] Add 18.9g of compound X (0.05mol) and 100g of pyridine to a 500mL three-necked flask, add 33.8g of trifluoromethanesulfonic anhydride (0.12mol) dropwise to 0~5℃, 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...

Embodiment 2

[0073] Example 2 Synthesis of raw material B

[0074]

[0075] 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 reaction for 20 hours; after the reaction, cooling, filtering, rotating 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, test value: 598.3066.

[0077] 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.

Embodiment 3

[0078] Example 3 Synthesis of Compound 1

[0079] synthetic route:

[0080]

[0081] 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%;

[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 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 an organic light emission diode device containing a 10, 10-diaryl anthrone compound and an application thereof. The device comprises a hole transport layer, a light emission layer and an electron transport layer. The material of the light emission layer of the device is a compound with 10, 10-diaryl anthrone as a core group, and the structural formula of the compound is shown in the general formula (1). According to the material with the 10, 10-diaryl anthrone as the core group, due to a small triplet and singlet energy difference, energy transfer between host and guest materials can be realized easily, energy that is originally lost in a heat form is easily available, and the high efficiency of the device can be acquired more easily. Further, when a fluorescent material is selected as a doped material, light emission radiation of the doped material is acquired more easily, and a long service life of the material can be acquired more easily.

Description

Technical field [0001] The present invention relates to the field of semiconductor technology, and in particular to an organic electroluminescent device whose light-emitting layer material is a compound with 10,10-diarylanthrone as the core and its application. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a broad 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 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 ...

Claims

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Application Information

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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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