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A kind of condensed ring compound containing boron atom and sulfur atom and its preparation method and application

A compound and fused ring technology, applied in the field of fused ring compounds and their preparation, can solve the problems of reduced external quantum efficiency of devices and complex device structures, etc.

Active Publication Date: 2022-02-22
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 vibrational 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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  • A kind of condensed ring compound containing boron atom and sulfur atom and its preparation method and application
  • A kind of condensed ring compound containing boron atom and sulfur atom and its preparation method and application
  • A kind of condensed ring compound containing boron atom and sulfur atom and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071]

[0072] Under an argon atmosphere, add m-1 (30.0g, 0.11mol) and sodium thiophenate (43.6g, 0.33mol) to a 500mL three-necked flask, add 180mL of N-methylpyrrolidone (NMP) to the bottle, and heat up to 150°C, stirred and reacted for 10 hours under the protection of argon, then cooled to room temperature, diluted the reaction solution with toluene and poured it into water, separated the organic phase, added anhydrous sodium sulfate to dry, filtered the obtained organic phase to remove the solvent, The crude product was separated by column to obtain the product m-2 (23.0 g, yield: 46%).

[0073] Elemental analysis structure (C 18 h 12 Br 2 S 2 ): theoretical value C, 47.81; H, 2.67; S, 14.18 test value C, 47.72; H, 2.73; S, 14.26.

[0074] Electrospray mass spectrometry (ESI-MS): theoretical value 452.2; experimental value 452.2 (M + ).

[0075] Under argon atmosphere, m-2 (5.0g, 11.1mmol) and dry o-xylene (80mL) were added to a 250mL two-necked flask, and butylli...

Embodiment 2

[0082]

[0083]Under an argon atmosphere, add m-4 (10.0g, 0.05mol) and sodium thiophenate (16.5g, 0.13mol) to a 250mL three-necked flask, add 80mL of N-methylpyrrolidone (NMP) to the bottle, and heat up to 150°C, stirred and reacted for 10 hours under the protection of argon, then cooled to room temperature, diluted the reaction solution with toluene and poured it into water, separated the organic phase, added anhydrous sodium sulfate to dry, filtered the obtained organic phase to remove the solvent, The crude product was separated by column to obtain the product m-5 (4.5 g, yield: 24%).

[0084] Elemental analysis structure (C 18 h 13 BrS 2 ): theoretical value C, 57.91; H, 3.51; S, 17.18 test value C, 57.96; H, 3.53; S, 17.18.

[0085] ESI-MS: theoretical value 372.0; experimental value 372.1 (M + ).

[0086] Under argon atmosphere, m-5 (1.5g, 4.0mmol) and dry o-xylene (70mL) were added to a 250mL two-necked flask, and butyllithium solution (1.7mL, 2.5 M, 4.2mmol), ...

Embodiment 3

[0097]

[0098] Under an argon atmosphere, magnesium chips (0.14g, 5.78mmol) were added to a 100mL two-necked flask, and m-3 (2.0g, 5.25mmol) was dissolved in 30mL of dry THF solution and added dropwise to a flask containing magnesium In a two-necked flask with crumbs, filter the obtained Grignard reagent, and slowly add it dropwise to a THF solution of trimethyl borate (0.82g, 7.9mmol) at -70°C. After the reaction, slowly pour the reaction solution into the fast In a stirring ice-water bath, add hydrochloric acid and stir for 30 min, the mixture is extracted with ether, the organic phase is washed with deionized water, dried with anhydrous sodium sulfate, the organic phase is concentrated and dried, and the crude product is recrystallized with hot n-hexane The product 1-46 was obtained (1.3 g, yield: 71%).

[0099] Elemental analysis structure (C 18 h 12 B 2 o 2 S 2 ): theoretical value C, 62.48; H, 3.50; S, 18.53 test value C, 62.41; H, 3.53; S, 18.52.

[0100] ESI-...

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Abstract

The invention provides a condensed ring compound containing a boron atom and a sulfur atom and a preparation method thereof. The condensed ring compound has a structure of formula I. The fused ring compound adopts boron / thiabridized fused ring unit as the light-emitting unit, and utilizes the resonance effect between boron and sulfur atoms to realize the separation of HOMO and LUMO, thereby achieving a small ΔE ST And the TADF effect, while the boron / thiabridized fused ring unit has a rigid skeleton structure, which can reduce the degree of relaxation of the excited state structure, thereby achieving a narrower half-peak width. In addition, the introduction of different substituents on the backbone of the boron / thiaride fused ring unit can further adjust the half-peak width. Using the luminescent compound of the invention as the luminescent layer of the electroluminescence device can realize narrow electroluminescence half-peak width and high external quantum efficiency of the device without needing a filter and a microcavity structure.

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 boron atoms and sulfur atoms and a preparation method and application thereof. 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) Composition with the cathode, 1~2 organic layers can be omitted as required, and the holes (Hole) injected through the positive and negative electrodes on the organic film are combined with electrons (Electron) to form excitons...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F9/6596C09K11/06H01L51/54
CPCC07F5/02C07F9/6596C09K11/06C09K2211/1096H10K85/656H10K85/657
Inventor 王利祥邵世洋陈凡赵磊王兴东李伟利王淑萌吕剑虹田洪坤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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