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Polyarylene ether/polyarylene sulfide with thermally activated delayed fluorescence effect and its preparation method and application

A thermal activation delay, polyarylene sulfide technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, luminescent materials, etc., can solve problems such as unfavorable device performance, low skeleton triplet energy level, affecting luminous efficiency, etc.

Active Publication Date: 2020-04-03
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

Most of the existing TADF polymers suitable for solution processing have low triplet energy levels in the skeleton, and the triplet energy of the light-emitting unit is easily transferred back to the main chain, which affects the luminous efficiency, which is not conducive to improving the performance of the device, and it is not easy to obtain blue light emission.

Method used

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  • Polyarylene ether/polyarylene sulfide with thermally activated delayed fluorescence effect and its preparation method and application
  • Polyarylene ether/polyarylene sulfide with thermally activated delayed fluorescence effect and its preparation method and application
  • Polyarylene ether/polyarylene sulfide with thermally activated delayed fluorescence effect and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0198] Embodiment 1: the synthesis of polymer Ⅰ-1

[0199] (1) Material number m-1

[0200] The reaction equation is as follows:

[0201]

[0202]The specific steps are: in a 1000ml three-neck round bottom flask, N-phenylanthranilic acid (108.61g, 0.5mol) was dissolved in methanol (300ml). Thionyl chloride (76ml) was carefully added dropwise. React at 60°C for 12h. After the reaction is completed, cool down to room temperature, add saturated aqueous sodium bicarbonate solution, extract the organic phase with dichloromethane, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and use a mixed solvent of petroleum ether:dichloromethane=5:1 as the eluent , and separated by silica gel column chromatography to obtain 110 g of yellow solid with a yield of 95%. 1 H NMR (400MHz, DMSO, δppm): 9.32(s, 1H), 7.90(d, J=8.0Hz, 1H), 7.44–7.33(m, 3H), 7.24(t, J=7.7Hz, 3H), 7.09 (t, J = 7.2Hz, 1H), 6.81 (t, J = 7.5Hz, 1H), 3.86 (s, 3H).

[0203] (2) Material n...

Embodiment 2

[0228] Embodiment 2: the synthesis of polymer I-2

[0229] The reaction equation is as follows:

[0230] The specific steps are: add m-6 (0.2g, 0.22mmol), resorcinol (0.0242g, 0.22mmol) and potassium carbonate (0.0730g, 0.53mmol) into a Schlenk bottle with an oil-water separator and a spherical condenser After adding 1ml N,N-dimethylacetamide and 1.5ml toluene, heated and stirred at 120°C for 3h under argon atmosphere, then raised the temperature to 150°C, reacted for 2h, and finally raised the temperature to 170°C, reacted for 24h. After the reaction, the reaction solution was poured into chloroform, the organic phase was washed three times with saturated brine and then dried with anhydrous sodium sulfate. After the organic phase was concentrated, it was settled in n-hexane, and the obtained yellow powdery solid was extracted with acetone for 24 hours. , extracted with methanol for 24 hours, and dried in vacuo to obtain 0.14 g of the product with a yield of 64%.

[0231] ...

Embodiment 3

[0234] Embodiment 3: the synthesis of polymer I-3

[0235] The reaction equation is as follows:

[0236]

[0237] The specific steps are: add m-6 (0.2g, 0.22mmol), hydroquinone (0.0242g, 0.22mmol) and potassium carbonate (0.0730g, 0.53mmol) into a Schlenk bottle with an oil-water separator and a spherical condenser After adding 1ml N,N-dimethylacetamide and 1.5ml toluene, heated and stirred at 120°C for 3h under argon atmosphere, then raised the temperature to 150°C, reacted for 2h, and finally raised the temperature to 170°C, reacted for 24h. After the reaction, the reaction solution was poured into chloroform, the organic phase was washed three times with saturated brine and then dried with anhydrous sodium sulfate. After the organic phase was concentrated, it was settled in n-hexane, and the obtained yellow powdery solid was extracted with acetone for 24 hours. , extracted with methanol for 24 hours, and dried in vacuo to obtain 0.16 g of the product with a yield of 73%...

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Abstract

The invention provides a polyarylene ether / polyarylene sulfide with heat-activated delayed fluorescence effect and its preparation method and application, belonging to the technical field of organic photoelectric materials. The structural formula of the polyarylene ether / polyarylene sulfide with thermally activated delayed fluorescence effect is shown in formula (I). The TADF unit in this structure is embedded between the saturated oxygen atoms / sulfur atoms in the polyarylene ether / polyarylene sulfide backbone, benefiting from the advantage that the oxygen atom / sulfur atom can break the conjugation, the triplet energy level of the main chain is relatively low. High, it can inhibit the reverse transfer of triplet energy from the light-emitting unit to the main chain, the luminous efficiency is higher, and it is easier to get blue light emission. The invention also provides a preparation method of polyarylene ether / polyarylene sulfide with heat-activated delayed fluorescence effect. The invention provides the application of the polyarylene ether / polyarylene sulfide with TADF effect in organic light-emitting diodes, which has excellent device performance and meets the requirements of solution processing devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a polyarylene ether / polyarylene sulfide having a thermally activated delayed fluorescence (TADF) effect and a preparation method and application thereof. Background technique [0002] In order to meet people's requirements for information display devices, OLED displays with characteristics such as self-luminescence, wide viewing angle, and short response time have emerged as the times require. Searching for new and efficient light-emitting materials, studying their light-emitting mechanism, and preparing high-performance, low-cost devices are the hottest topics in OLED scientific research and product development. [0003] The development of organic electroluminescent materials has gone through three generations: the first generation of ordinary fluorescent materials, in the case of electroluminescence, triplet excitons are wasted in the form of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/40C09K11/06H01L51/50H01L51/54
CPCC09K11/06C08G65/4037C08G65/4093C09K2211/1425H10K85/111H10K50/00
Inventor 丁军桥刘心蕊饶建成王淑萌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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