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Amboceptor polysubstituted carbazole compound with TADF (thermal active delay fluorescence), preparation method of compound and application of compound

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: 2019-01-04
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Amboceptor polysubstituted carbazole compound with TADF (thermal active delay fluorescence), preparation method of compound and application of compound
  • Amboceptor polysubstituted carbazole compound with TADF (thermal active delay fluorescence), preparation method of compound and application of compound
  • Amboceptor polysubstituted carbazole compound with TADF (thermal active delay fluorescence), preparation method of compound and application of compound

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Effect test

Embodiment 1

[0045] Embodiment 1: Synthesis of 4Cz-DOXD

[0046] 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).

[0047]

Embodiment 2

[0048] Embodiment 2: Synthesis of 4TCz-DOXD

[0049] 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).

[0050]

Embodiment 3

[0051] Embodiment 3: Synthesis of 4Cz-tBu

[0052] 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).

[0053]

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Abstract

The invention discloses an amboceptor polysubstituted carbazole compound with TADF (thermal active delay fluorescence), a preparation method of the compound and an application of the compound. The structure of the compound is as shown in the specification. The preparation method of the compound includes the steps: taking polyfluorinated 1, 4-double (5-phenyl-1, 3, 4-oxadiazole-2) benzene derivative or perfluorinated 4, 4'-dimethyl-1, 1'-biphenyl as a raw material; adding carbazole, alkali and organic solvents; performing reaction on mixture in nitrogen atmosphere to obtain the compound. The TADF material has high PLQY (photoluminescence quantum yield) under pure solid state and high electroluminescence efficiency when serving as a luminescence objected to be applied into OLEDs (organic light emitting diodes).

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 Applications(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 UNIV OF TECH
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