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A kind of double-acceptor type multi-substituted carbazole compound with tadf characteristic and its preparation method and application

A compound and multi-substitution technology, applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of low fluorescence quantum efficiency and low device efficiency, achieve high electroluminescence efficiency, and easy operation , the effect of mild conditions

Active Publication Date: 2020-12-25
NANJING TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of double acceptor type multi-substituted carbazole compound with TADF characteristic, to solve the existing TADF fluorescent dye with oxadiazole and trifluoromethyl as single electron acceptor in pure solid condition The low fluorescence quantum efficiency is not high, and the device efficiency is low

Method used

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  • A kind of double-acceptor type multi-substituted carbazole compound with tadf characteristic and its preparation method and application
  • A kind of double-acceptor type multi-substituted carbazole compound with tadf characteristic and its preparation method and application
  • A kind of double-acceptor type multi-substituted carbazole compound with tadf characteristic and its preparation method and application

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Experimental program
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Embodiment 1

[0043] Embodiment 1: Synthesis of 4Cz-DOXD

[0044] 5,5'-(perfluoro-1,4-phenylene)bis(2-phenyl-1,3,4-oxadiazole) (0.5g, 1.14mmol), carbazole (1.14g, 6.84mmol ), K 2 CO 3(2.84g, 20.53mmol), DMSO 20ml, under the protection of nitrogen, heated at 150°C for 12h. After cooling to room temperature, it was poured into 200 ml of saturated saline and stirred, and a large amount of yellow solid was precipitated, which was filtered by suction and purified by column chromatography to obtain 1 g of a yellow solid product with a yield of 85%. 1H NMR (CDCl 3 ,303k, 500Hz):δ=7.736-7.685(d,8H),7.351-7.315(d,10H),7.160-7.088(t,12H),7.083-7.017(t,8H),6.805-6.754(d, 4H).

[0045]

Embodiment 2

[0046] Embodiment 2: Synthesis of 4TCz-DOXD

[0047] 5,5'-(perfluoro-1,4-phenylene)bis(2-phenyl-1,3,4-oxadiazole) (0.5g, 1.14mmol), 3,6-di-tert-butyl Carbazole (1.91g, 6.84mmol), K 2 CO 3 (2.84g, 20.53mmol), DMSO 20ml, under the protection of nitrogen, heated at 150°C for 12h. After cooling to room temperature, it was poured into 200 ml of saturated saline and stirred, and a large amount of yellow solid was precipitated, which was filtered by suction and purified by column chromatography to obtain 1.45 g of a yellow solid product with a yield of 85%. 1H NMR (CDCl 3 ,303k, 500Hz):δ=7.60(s,8H),7.351-7.315(d,2H),7.182-7.129(d,12H),7.129-7.076(d,8H), 6.988-6.937(d,4H) ,1.31(s,72H).

[0048]

Embodiment 3

[0049] Embodiment 3: Synthesis of 4Cz-tBu

[0050] 5,5'-(perfluoro-1,4-phenylene)bis(2-(4-(tert-butyl)phenyl)-1,3,4-oxadiazole) (0.5g, 0.98mmol) , carbazole (0.911g, 5.45mmol), K 2 CO 3 (2.26g, 16.35mmol), DMSO 20ml, under nitrogen protection, heated at 150°C for 12h. After cooling to room temperature, it was poured into 200 ml of saturated saline and stirred. A large amount of yellow solid was precipitated, which was filtered by suction and purified by column chromatography to obtain 0.96 g of a yellow solid product with a yield of about 85%. 1H NMR (CDCl 3 ,303k, 500Hz):δ=7.742-7.690(s,8H),7.340-7.034(d,8H),7.149-7.086(t,12H),7.086-7.020(t,8H),6.738-6.685(d, 4H), 1.27(s, 18H).

[0051]

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Abstract

The invention discloses a double-receptor type multi-substituted carbazole compound with TADF characteristics, a preparation method and application thereof. The structure of the compound is shown in formula I. The preparation method of the compound comprises the following steps: 1,4-bis(5-phenyl-1,3,4-oxadiazol-2-yl) benzene derivatives substituted with polyfluorine or perfluoro-substituted 4, 4'-Dimethyl-1,1'-biphenyl is used as raw material, and it is obtained by adding carbazole, alkali and organic solvent, and reacting under nitrogen atmosphere. The TADF material provided by the invention has very high PLQY in pure solid state, and it has high electroluminescence efficiency when applied in OLEDs as a light-emitting object.

Description

technical field [0001] The invention relates to a heat-activated delayed fluorescent material, in particular to a double-receptor type multi-substituted carbazole compound with TADF characteristics and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of light weight, wide viewing angle, low driving voltage, fast response, and flexible display, and are considered to be the next-generation display technology to replace liquid crystal displays. At present, the materials that have been commercially used in OLEDs are mainly phosphorescent materials of noble metal complexes, but their large-scale application is limited due to the scarcity and high price of their resources. Thermally activated delayed fluorescence (TADF) can realize the triplet state (T 1 ) to the singlet state (S 1 ) in the anti-intersystem crossing process, its triplet state can also be effectively utilized to emit light effectively,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D413/14C09K11/06H01L51/54
CPCC09K11/06C07D209/86C07D413/14C09K2211/1048C09K2211/1029C09K2211/1007H10K85/6572H10K85/657
Inventor 陶友田张睦灿袁文博
Owner NANJING TECH UNIV
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