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An organic electroluminescent device containing 10,10-diarylanthrone compounds 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: 2019-08-06
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 through 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 materials has a serious roll-off at high current densities.

Method used

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  • An organic electroluminescent device containing 10,10-diarylanthrone compounds and its application
  • An organic electroluminescent device containing 10,10-diarylanthrone compounds and its application
  • An organic electroluminescent device containing 10,10-diarylanthrone compounds and its application

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Experimental program
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Effect test

Embodiment 1

[0067] The preparation of embodiment 1 compound 1

[0068]

[0069] In a 1L three-necked flask equipped with a constant pressure dropping funnel, metal magnesium (5.1g, 0.21mol) was added, p-bromoiodobenzene (56.6g, 0.20mol) was dissolved in 300g tetrahydrofuran, and placed in a constant pressure drop In the funnel, use nitrogen protection, heat the three-necked flask until the temperature in the bottle reaches 65°C, add the tetrahydrofuran solution of p-bromoiodobenzene through the constant pressure dropping funnel, first add 50mL, after the reaction is triggered, slowly drop the remaining part, 1h After completion of the dropwise addition, react for 2 h at reflux temperature, and transfer to a constant pressure funnel after cooling down to room temperature for use;

[0070] Dissolve anthraquinone (41.6g, 0.20mol) in 200g tetrahydrofuran and add it to a 2L three-neck flask, then slowly add the above-mentioned solution for use dropwise, and react at reflux temperature for 3...

Embodiment 2

[0074] The preparation of embodiment 2 compound 2

[0075]

[0076] In a 250ml three-necked flask, under the protection of nitrogen, add 8.51g (0.02mol) of compound 1, 7.62g (0.03mol) of bis-boronic acid pinacol ester, 3.92g (0.04mol) of potassium acetate, 0.30g pd 2 (dba) 3 , 0.20g of tri-tert-butylphosphine, 100ml of toluene, heated to reflux for 20 hours, took a sample and spotted the plate, and the reaction was complete; naturally cooled, filtered, and the filtrate was rotary evaporated, and column chromatography gave compound 2 with a HPLC purity of 99.7% and a yield of 87.57%.

[0077] High-resolution mass spectrometry, ESI source, positive ion mode, molecular formula C32H29BO3, theoretical value 472.2210, test value 472.2215.

[0078] Elemental analysis (C32H29BO3): theoretical value C: 81.36, H: 6.19, O: 10.16, test value: C: 81.40, H: 6.15, O: 10.18.

Embodiment 3

[0079] The preparation of embodiment 3 compound 3

[0080]

[0081] In a 1L three-necked flask equipped with a constant-pressure dropping funnel, metal magnesium (5.1g, 0.21mol) was added, and s-tribromobenzene (63.0g, 0.2mol) was dissolved in 300g of tetrahydrofuran, and placed in a constant-pressure drop In the funnel, use nitrogen protection, heat the three-necked flask until the temperature in the bottle reaches 65°C, add the tetrahydrofuran solution of tribromobenzene through the constant pressure dropping funnel, first add 50mL, after the reaction is triggered, slowly add the remaining part, 1h After the dropwise addition, react at reflux temperature for 2 h, and transfer to a constant pressure funnel after cooling down to room temperature for use. Dissolve anthraquinone (41.6g, 0.2mol) in 200g tetrahydrofuran and add it to a 2L three-neck flask, then slowly add the above-mentioned solution for use dropwise, and react at reflux temperature for 3h. The solution was sl...

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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 invention relates to the technical field of semiconductors, in particular to an organic electroluminescent device whose light-emitting layer material is a compound with 10,10-diaryl anthrone as the core and its application. 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 electrodes at both...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/54H01L51/50
CPCH10K85/00H10K85/615H10K50/00H10K2102/00H10K2102/301
Inventor 李崇张兆超王立春
Owner VALIANT CO LTD
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