Condensed ring compound containing two boron atoms and four chalcogen atoms and organic electroluminescent device

A technology of boron atoms and compounds, which is applied to compounds containing group 3/13 elements of the periodic table, electrical solid devices, electrical components, etc., can solve problems such as complex device structures and reduced external quantum efficiency of devices, and achieve high luminous efficiency , Promote intersystem crossing, high device external quantum efficiency

Pending Publication Date: 2022-04-15
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this D-A structure exhibits a large Stokes shift due to the vibrational relaxation of its excited state, and the luminescence spectrum is wide, and the half-maximum width (FWHM) is generally 70-100n...

Method used

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  • Condensed ring compound containing two boron atoms and four chalcogen atoms and organic electroluminescent device
  • Condensed ring compound containing two boron atoms and four chalcogen atoms and organic electroluminescent device
  • Condensed ring compound containing two boron atoms and four chalcogen atoms and organic electroluminescent device

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preparation example Construction

[0059] The present invention has no special limitation on the preparation method of the condensed ring compound, and a typical preparation process thereof is as follows:

[0060]

[0061] Another typical preparation process is as follows:

[0062]

[0063] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode; the organic thin film layer includes the condensed ring compound shown in the above formula (I) .

[0064] The present invention has no special restrictions on the structure of the organic electroluminescent device, and conventional organic electroluminescent devices well known to those skilled in the art can be used, and those skilled in the art can select and adjust according to application conditions, quality requirements and product requirements , The structure of the organic electroluminescence device in the present invention preferably include...

Embodiment 1

[0078] The reaction formula is as follows:

[0079]

[0080] Under argon atmosphere, 1,2,4-tribromo-3,5,6-trifluorobenzene (6.7g, 18.1mmol), phenol (5.1g, 54.4mmol) and potassium carbonate ( 7.5g, 54.4mmol), add 100mL N,N-dimethylformamide (DMF) into the bottle, raise the temperature to 80°C, stir the reaction under the protection of argon for 24 hours, then cool to room temperature, pour the reaction solution into In water (1000 mL), the solid was filtered out, and the solvent was removed by suction, and the crude product was separated by column to obtain product m-1 (3.3 g, yield: 31%).

[0081] Elemental analysis structure (C 24 h 15 Br 3 o 3 ): theoretical value C, 48.77; H, 2.56 test value C, 48.62; H, 2.63.

[0082] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS): theoretical value 587.9; experimental value 587.9.

[0083] Under argon atmosphere, add diphenyldiselenide (10.0g, 32.0mmol), sodium borohydride (2.4g, 64.0m...

Embodiment 2

[0090] The reaction formula is as follows:

[0091]

[0092] Under argon atmosphere, 1,2,4,5-tetrabromo-3,6-difluorobenzene (7.8g, 18.1mmol), p-cresol (3.9g, 36.2mmol) and Potassium carbonate (5.0g, 36.2mmol), 100mL of N,N-dimethylformamide (DMF) was added to the bottle, the temperature was raised to 80°C, and the reaction was stirred for 24 hours under the protection of argon, then cooled to room temperature, and the reaction The solution was poured into water (1000mL), the solid was filtered out, and the solvent was removed by pumping. The crude product was separated by column to obtain the product m-3 (3.6g, yield: 33%).

[0093] Elemental analysis structure (C 20 h 14 Br 4 o 2 ): theoretical value C, 39.64; H, 2.33 test value C, 39.57; H, 2.30.

[0094] MALDI-TOF-MS: theoretical value 601.8; experimental value 601.8.

[0095] Under argon atmosphere, m-4 (bis(4-methylphenyl) diselenide) (21.8g, 64.0mmol), sodium borohydride (4.8g, 128.0mmol) and 300mL DMF were adde...

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Abstract

The invention provides a fused ring compound containing boron atoms and selenium or tellurium atoms. The fused ring compound is shown as a formula (I). Compared with the prior art, the condensed ring compound containing boron atoms and selenium or tellurium atoms is adopted as the light-emitting unit, on one hand, the relaxation degree of an excited state structure can be reduced by utilizing a rigid framework structure of the organic boron condensed ring compound, and therefore the narrow half-peak width is achieved; on the other hand, intersystem crossing is promoted through the heavy atom effect of selenium or tellurium atoms, the delayed fluorescence effect is activated, and therefore high luminous efficiency is achieved. Meanwhile, by changing the types of aromatic rings or heteroaromatic rings contained in the fused ring compound, the delayed fluorescence lifetime and the half-peak width can be further adjusted. Experimental results show that when the luminescent compound is used as a luminescent layer of the electroluminescent device, narrow electroluminescent half-peak width can be realized without an optical filter and a microcavity structure, and high external quantum efficiency of the device can also be realized.

Description

technical field [0001] The invention belongs to the technical field of materials, in particular to a condensed ring compound containing two boron atoms and four oxygen group atoms and an organic electroluminescent device. Background technique [0002] Organic light-emitting devices (OLEDs) are usually composed of a cathode, an anode, and an organic layer inserted between the cathode and the anode, generally including a transparent ITO anode, a hole injection layer (TIL), a hole transport layer (HTL), and a light emitting layer (EL). ), hole-blocking layer (HBL), electron-transporting layer (ETL), electron-injecting layer (EIL) and cathode, and 1-2 organic layers can be omitted as required. The mechanism of action is to form a voltage between two electrodes, from the cathode When electrons are injected, holes are injected from the anode. The electrons and holes combine to form an excited state in the light-emitting layer, and the excited state radiates back to the ground stat...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/027C09K11/06C09K2211/1096C09K2211/1085C09K2211/1055H10K85/636H10K85/657H10K85/322H10K50/11
Inventor 王利祥邵世洋陈凡吕剑虹赵磊王兴东李伟利王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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