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[7] helicene organic light-emitting material based on triaryl borane and application of [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission

A technology of triarylborane and luminescent materials, which is applied in the field of sign inversion of circularly polarized luminescence, can solve problems such as 7B-HC structural instability, increase the asymmetry factor of luminescence, have universal applicability, and be easy to scale production Effect

Active Publication Date: 2021-06-22
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, 7B-HC is structurally unstable

Method used

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  • [7] helicene organic light-emitting material based on triaryl borane and application of [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission
  • [7] helicene organic light-emitting material based on triaryl borane and application of [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission
  • [7] helicene organic light-emitting material based on triaryl borane and application of [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission

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preparation example Construction

[0034] The present invention also provides a method for preparing a triarylborane-based [7]helicene organic luminescent material, comprising:

[0035] Halide precursors are used as raw materials to carry out borylation reaction to obtain.

[0036] In some embodiments, the halide precursor is a bromide / iodide precursor.

[0037] In some embodiments, the bromide precursor is 9-bromo[7]helicene; the bromide precursor 9-bromo[7]helicene (9Br-[7]HC) is obtained through benzyl(dibromo) Methane coupling reactions were obtained according to published procedures.

[0038] In some embodiments, the iodide precursor is 9-(2-iodophenyl)[7]helicene. 9B(OH) 2 The Suzuki coupling reaction of -[7]HC with o-diiodobenzene proceeds very smoothly, providing the iodide precursor 9-(2-iodophenyl)[7]helicene (9I Ph-[7] HC).

[0039] In some embodiments, the borylation reaction includes: lithiation of n-butyllithium and quenching of micyl borofluoride. [7]helicenes based on triarylboranes are al...

Embodiment 1

[0043] 9-Micylboron[7]helicene (9B-[7]HC):

[0044] To a solution of 9-bromo[7]helicene (9Br-[7]HC) (700 mg, 1.53 mmol) in anhydrous THF (40 mL) was slowly added dropwise n-butyllithium (1.2 mL, 1.6M, 1.84mmol) in n-hexane. The mixture was stirred at the same temperature for 1 hour. A solution of micyl borofluoride (1.23 g, 4.59 mmol) in anhydrous THF (10 mL) was added via syringe. The reaction mixture was slowly warmed to room temperature and stirred overnight. with saturated NH 4 The reaction was quenched with Cl solution, and the organic phase was washed with CH 2 Cl 2 extraction. The combined organic layers were washed with anhydrous Na 2 SO 4 Dry, filter, and concentrate under reduced pressure. The resulting residue was subjected to silica gel column chromatography (20 / 1 petroleum ether / CH 2 Cl 2 , R f =0.38) purification afforded 508 mg (0.81 mmol) of 9B-[7]HC as a yellow solid in 53% yield: mp 318.0°–319.0°C; [α] 25 (P)-isomer is +680.8, (M)-isomer is –700....

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Abstract

The invention belongs to the field of organic light-emitting materials, and relates to a [7] helicene organic light-emitting material based on triaryl borane and application of the [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission. Two triaryl borane-based [7] helical alkenes are disclosed which contain one meryl boron or 2-(meryl boron) phenyl substituent in the 9-position of the [7] helical backbone. The substituent group is changed from the rice boron to the 2-(rice boron) phenyl group, so that the GLUM is increased by two times. Circularly polarized light emission and sign reversal.

Description

technical field [0001] The invention belongs to the field of organic luminescent material chemistry, and in particular relates to the sign inversion of circularly polarized luminescence induced by substituents in triarylborane-based [7]helicene. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Circularly polarized luminescence (CPL) refers to the differential emission between left and right circularly polarized light produced by an intrinsic chiral light emitting system or an achiral system in a chiral environment. CPL active materials refer to materials that can directly emit CPL without the use of circular polarizing filters. CPL active materials are emerging as key cha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/027C09K11/06C09K2211/1011C09K2211/1007C09K2211/1014
Inventor 赵翠华李寒伟赵正华
Owner SHANDONG UNIV
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