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Fused ring compound containing four boron atoms, preparation method thereof and electroluminescent device

A compound and boron atom technology, applied in the field of organic light-emitting materials, can solve the problems of complex device structure and reduced external quantum efficiency of the device, and achieve the effects of reducing the degree of relaxation, narrowing the half-peak width, and high external quantum efficiency of the device

Pending Publication Date: 2022-05-10
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 obvious vibration relaxation of the excited state, and the luminescence spectrum is wide, and the half-maximum width (FWHM) is generally 70-100nm. In practical applications, filtering is usually required. sheet or construct an optical microcavity to improve the color purity, but this will lead to a decrease in the external quantum efficiency of the device or a complicated device structure

Method used

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  • Fused ring compound containing four boron atoms, preparation method thereof and electroluminescent device
  • Fused ring compound containing four boron atoms, preparation method thereof and electroluminescent device
  • Fused ring compound containing four boron atoms, preparation method thereof and electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069]

[0070] Under argon atmosphere, 1-1 (10.0g, 0.032mol), two m-toluidine (4.52g, 0.027mol), tris(dibenzylideneacetone) dipalladium (0.293g, 0.32 mmol), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (BINAP, 0.300g, 0.48mmol) and sodium tert-butoxide (9.23g, 0.096mol), add 240mL of toluene and heat up to 100°C , stirred for 5 hours. After cooling to room temperature, the reaction solution was extracted with 200 mL of ether, washed three times with saturated brine (200 mL×3), the organic phases were combined, dried by adding anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained solid was separated through a silica gel column to obtain Product 1-2 (10.7 g, yield: 78%).

[0071] Elemental analysis structure (C 20 h 17 Br 2 N): theoretical value C, 55.71; H, 3.97; N, 3.25; test value C, 55.71; H, 3.98; N, 3.25.

[0072] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF) mass spectrometry: ...

Embodiment 2

[0094]

[0095] Under argon atmosphere, 1-1 (10.0g, 0.032mol), phenoxazine (4.94g, 0.027mol), tris(dibenzylideneacetone) dipalladium (1.47g, 1.60mmol) were added to a 500mL three-necked flask ), tri-tert-butylphosphonium tetrafluoroborate (1.86g, 6.40mmol) and sodium tert-butoxide (10.4g, 0.108mol), add 210mL of toluene. The temperature was raised to 105°C, and the reaction was stirred for 3.5 hours. After cooling to room temperature, the reaction solution was extracted with 200 mL of ether, washed three times with saturated brine (200 mL×3), the organic phases were combined, dried by adding anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained solid was separated through a silica gel column to obtain Product 2-1 (9.3 g, yield: 70%).

[0096] Elemental analysis structure (C 18 h 11 Br 2 NO): Theoretical C, 51.83; H, 2.66; N, 3.36; O, 3.84; Tested C, 51.81; H, 2.66; N, 3.35.

[0097] MALDI-TOF mass spectrum: theoretical val...

Embodiment 3

[0119]

[0120] Under argon atmosphere, 1-2 (10.0g, 0.023mol), 3,5-dimethylaniline (8.36g, 0.069mol), tris(dibenzylideneacetone) dipalladium ( 0.210g, 0.23mmol), BINAP (0.218g, 0.35mmol) and sodium tert-butoxide (6.73g, 0.070mol), add 240mL of toluene. The temperature was raised to 100°C, and the reaction was stirred for 24 hours. After cooling to room temperature, the reaction solution was extracted with 150 mL of ether, washed three times with saturated brine (200 mL×3), the organic phases were combined, dried by adding anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained solid was separated through a silica gel column to obtain Product 3-1 (9.1 g, yield: 77%).

[0121] Elemental analysis structure (C 36 h 37 N 3 ): theoretical value C, 84.50; H, 7.29; N, 8.21; test value C, 84.48; H, 7.29; N, 8.20.

[0122] MALDI-TOF mass spectrum: theoretical value 511.3; experimental value 511.2 (M + ).

[0123] Under an argon atmo...

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Abstract

The invention relates to a fused ring compound containing four boron atoms, a preparation method of the fused ring compound and an electroluminescent device, and belongs to the technical field of organic luminescent materials. The fused ring compound has a structure as shown in a formula (I). The fused ring compound is characterized in that four boron atoms and nitrogen atoms are embedded in a fused ring molecular skeleton, separation of HOMO and LUMO is realized by utilizing a resonance effect between the boron atoms and the nitrogen atoms, so that relatively small delta EST and TADF effects are realized, meanwhile, the relaxation degree of an excited state structure can be reduced by virtue of a rigid skeleton structure of the fused ring compound, and the molecular weight of the fused ring compound is reduced. Therefore, a narrow half-peak width is realized. Experimental results show that when the condensed ring compound is adopted as a light-emitting layer of the electroluminescent device, narrow electroluminescent half-peak width can be achieved under the condition that an optical filter and a microcavity structure are not needed, and high device external quantum efficiency can also be achieved. The preparation method of the fused ring compound containing four boron atoms has the advantages of mild conditions and high product yield.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a condensed ring compound containing four boron atoms, a preparation method thereof and an electroluminescence device. Background technique [0002] Organic electroluminescent devices (OLEDs) have the characteristics of rich colors, thin thickness, wide viewing angle, fast response, and flexible devices, and are considered to be the most promising next-generation flat panel display and solid-state lighting technologies. OLEDs are usually composed of ITO anode, hole injection layer (TIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) Composed of cathode and cathode, 1~2 organic layers can be omitted as needed, and the holes (Hole) injected from the positive and negative electrodes on the organic film combine with electrons (Electron) to form excitons...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/02C09K11/06C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1048C09K2211/1055C09K2211/1051C09K2211/1059C09K2211/1062C09K2211/1066C09K2211/107C09K2211/1074C09K2211/1077C09K2211/1081C09K2211/1085H10K85/636H10K85/631H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 王利祥邵世洋王一诺吕剑虹李伟利王兴东赵磊王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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