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Bora or phosphorus heterocyclic fused ring compound, preparation method thereof and luminescent device

A compound and condensed ring technology, which is applied in the fields of boron hetero or phosphor hetero condensed ring compounds and their preparation methods and light-emitting devices, can solve the problems of complex device structure and reduced external quantum efficiency of the device, and achieve high light-emitting efficiency, mild conditions, simple steps

Pending Publication Date: 2022-03-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • 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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  • Bora or phosphorus heterocyclic fused ring compound, preparation method thereof and luminescent device
  • Bora or phosphorus heterocyclic fused ring compound, preparation method thereof and luminescent device
  • Bora or phosphorus heterocyclic fused ring compound, preparation method thereof and luminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059]

[0060] Under argon atmosphere, m-1 (3.2g, 10.0mmol), 1-boronic naphthalene (1.7g, 10.0mmol), potassium carbonate (1.9g, 20.0mmol) and Pd(PPh 3 ) 2 Cl 2 (0.18g, 0.25mmol), 30mL of toluene was added, and the system was reacted at 120°C for 5h. After cooling to room temperature, deionized water was added thereto, and the organic phase extracted was dried with anhydrous sodium sulfate, and the solvent was removed. The crude product was separated by silica gel column chromatography to obtain product m-2 (3.2 g, yield: 44%).

[0061] Elemental analysis structure (C 16 h 10 BrCl): Theoretical: C, 60.51; H, 3.17; Found: C, 60.54; H, 3.12.

[0062] MALDI-TOF-MS: theoretical 316.0; experimental 316.0.

[0063] Under argon atmosphere, m-2 (3.2g, 10.0mmol), aniline (0.9g, 10.0mmol), sodium tert-butoxide (1.9g, 20.0mmol) and (AMPHOS) were added to a 250mL two-necked flask 2 PdCl 2 (0.35g, 0.5mmol), add o-xylene 60mL, and react the system at 120°C for 5h. After cooling t...

Embodiment 2

[0073]

[0074] Under argon atmosphere, m-5 (4.4g, 10.0mmol), 1-boronic naphthalene (1.7g, 10.0mmol), potassium carbonate (1.9g, 20.0mmol) and Pd(PPh 3 ) 2 Cl 2 (0.18g, 0.25mmol), 30mL of toluene was added, and the system was reacted at 120°C for 5h. After cooling to room temperature, deionized water was added thereto, and the organic phase extracted was dried with anhydrous sodium sulfate, and the solvent was removed. The crude product was separated by silica gel column chromatography to obtain product m-6 (1.8 g, yield: 40%).

[0075] Elemental analysis structure (C 30 h 30 ClN): Theoretical: C, 81.89; H, 6.87; N, 3.18; Found: C, 81.86; H, 6.83; N, 3.14.

[0076] MALDI-TOF-MS: theoretical 439.2; experimental 439.2.

[0077] Under argon atmosphere, add m-6 (4.4g, 10.0mmol), m-difluorobenzene (0.6g, 5.0mmol), cesium carbonate (6.5g, 20.0mmol) into a 250mL two-necked flask, add DMF 60mL, The system was reacted at 120°C for 5h. After being cooled to room temperature, dic...

Embodiment 3

[0084]

[0085] Under argon atmosphere, add m-8 (3.2g, 10.0mmol), 1-boronic acid naphthalene (1.7g, 10.0mmol), potassium carbonate (1.9g, 20.0mmol) and Pd(PPh 3 ) 2 Cl 2 (0.18g, 0.25mmol), 30mL of toluene was added, and the system was reacted at 120°C for 5h. After cooling to room temperature, deionized water was added thereto, and the organic phase extracted was dried with anhydrous sodium sulfate, and the solvent was removed. The crude product was separated by silica gel column chromatography to obtain product m-9 (1.6 g, yield: 49%).

[0086] Elemental analysis structure (C 15 h 9 BrClN): Theoretical: C, 56.55; H, 2.85; N, 4.40; Found: C, 56.58; H, 2.82; N, 4.43.

[0087] MALDI-TOF-MS: theoretical 317.0; experimental 317.0.

[0088] Under argon atmosphere, m-9 (3.2g, 10.0mmol), aniline (0.9g, 10.0mmol), sodium tert-butoxide (1.9g, 20.0mmol) and (AMPHOS) were added to a 250mL two-necked flask 2 PdCl 2 (0.35g, 0.5mmol), add o-xylene 60mL, and react the system at 120...

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Abstract

The invention relates to a boron-impurity or phosphorus-impurity fused ring compound, a preparation method thereof and a light-emitting device, and belongs to the technical field of organic light-emitting materials. The invention provides a boron-doped or phosphorus-doped fused ring compound which has a structure as shown in any one of formulas (I)-(IV). According to the boron-doped or phosphorus-doped fused ring compound provided by the invention, on one hand, the relaxation degree of an excited state structure can be reduced by utilizing a rigid skeleton structure of the fused ring compound, so that relatively narrow half-peak width is realized; on the other hand, separation of HOMO and LUMO is achieved through the resonance effect between boron atoms or phosphorus atoms and heteroatoms, and therefore small delta EST and TADF effects are achieved, and 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.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a bora or phosphorous heterocondensed ring compound, a preparation method thereof and a light-emitting device. Background technique [0002] Organic light-emitting 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 (Exciton...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C07F9/6571C07F9/6578C07F9/6584C09K11/06H01L51/54
CPCC07F5/02C07F7/0816C07F9/6584C07F9/657163C07F9/65785C09K11/06C09K2211/1014C09K2211/1029C09K2211/104C09K2211/1055C09K2211/1085C09K2211/1096H10K85/631H10K85/636H10K85/657H10K85/6572H10K85/40
Inventor 王利祥邵世洋陈凡王兴东赵磊吕剑虹李伟利王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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