Fluorene spirotriphenylamine derivative compound as well as preparation method and application thereof

A technology of fluorene spiro triphenylamine and derivatives is applied to the fluorene spiro triphenylamine derivative compound. In the field of preparation of the compound, problems such as low efficiency can be solved, and the effect of good application prospect, fast RISC rate and enhanced RISC rate can be achieved.

Pending Publication Date: 2022-03-01
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the low efficiency of the above-mentioned prior art, the present invention provides a differently modified fluorene spirotriphenylamine derivative compound, which can be used as an organic light-emitting material by adjusting the excited state configuration of the molecule change and suppress non-radiative transitions, making it a qualitative breakthrough in device efficiency and roll-off

Method used

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  • Fluorene spirotriphenylamine derivative compound as well as preparation method and application thereof
  • Fluorene spirotriphenylamine derivative compound as well as preparation method and application thereof
  • Fluorene spirotriphenylamine derivative compound as well as preparation method and application thereof

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Embodiment 1

[0056] The present embodiment provides a fluorene spirotriphenylamine derivative compound, the structural formula is shown in M1:

[0057]

[0058] The preparation method of this compound is as follows:

[0059]

[0060] S1. Preparation of 2-chloro-4-iodo-[1,1'-biphenyl]-3-carboxylic acid:

[0061] In a 250 mL flask, combine 2-bromo-3-methylbenzoic acid (4.59 g, 21.3 mmol), palladium acetate (0.24 g, 1.06 mmol), iodobenzenediacetic acid (6.68 g, 21.3 mmol) and iodine (5.42 g) , 21.3 mmol) was dissolved in N,N-dimethylformamide (50 mL). After stirring at 100 °C for 24 h, the reaction mixture was cooled to room temperature and diluted with 50 ml of ethyl acetate. 200 ml of aqueous hydrochloric acid (0.5N) was added to wash off N,N-dimethylformamide, and the crude product was extracted with ethyl acetate. 3 times. The organic phase was collected, washed with saturated brine, and dried over anhydrous sodium sulfate. Concentrate in vacuo at 0~700mbar by rotary evaporator fo...

Embodiment 2

[0073] This embodiment provides a fluorene spirotriphenylamine derivative compound, the preparation method of which is the same as that of embodiment 1, the difference lies in that, different from embodiment 1, the benzoic acid derivative used in S1 is The fluorene spirotriphenylamine derivative compound M2 is obtained, and the structural formula of M2 is shown below.

[0074]

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Abstract

The invention discloses a fluorene spirotriphenylamine derivative compound and a preparation method and application thereof, the structural formula of the fluorene spirotriphenylamine derivative compound is as follows: a series of fluorene spirotriphenylamine derivative organic light-emitting small molecules are prepared by introducing groups with different steric hindrances into ortho-positions of triazine based on triphenyltriazine as an electron withdrawing and triphenylamine as an electron donating; the fluorene spirotriphenylamine derivative has very good luminous intensity and extremely high fluorescence quantum yield; excited state configuration change and non-radiative transition of molecules are regulated and controlled through a steric effect, so that high efficiency of the molecules is realized; the compound can be used as a novel luminescent molecule with good performance, low cost and high luminescent intensity; the fluorene spirotriphenylamine derivative compound has remarkable economic value in the application aspects of preparation of luminescent materials, luminescent devices or intelligent materials and the like, and has a good application prospect in the fields of full-color display and solid-state illumination.

Description

technical field [0001] The present invention relates to the field of organic light-emitting materials, more particularly, to a fluorene spirotriphenylamine derivative compound, and the present invention also relates to a preparation method of the compound. Background technique [0002] The technology of organic light-emitting materials used as organic light-emitting diodes (OLEDs) has a wide range of applications in flat panel displays, smart phones, and solid-state light emitting. Significant advantages such as fast response speed and flexibility. It has huge application potential in the fields of flat panel display, smart phone and solid-state light-emitting, attracting extensive attention from academia and industry around the world. [0003] However, the performance of exciplex-based OLED devices still lags far behind those using conventional D-π-A-type TADF materials or phosphorescent emitters. The low electroluminescence efficiency is related to its low photoluminesce...

Claims

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Application Information

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IPC IPC(8): C07D401/10C09K11/06
CPCC07D401/10C09K11/06C09K2211/1029C09K2211/1059C09K2211/1007
Inventor 郑明辉陈文铖籍少敏霍延平伍昱岚陈绍鸿
Owner GUANGDONG UNIV OF TECH
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