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A kind of carboline trisubstituted derivative and its application

A derivative, carboline three technology, applied in the field of carboline derivatives, can solve the problems of incomplete utilization, device efficiency and service life decline, and achieve the effect of high triplet energy, balanced transmission capacity and high efficiency

Active Publication Date: 2022-07-22
ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In conventional OLED devices, the injection / transport speed of holes is usually several orders of magnitude faster than that of electrons. In OLED devices, the holes in the exciton compliance region are significantly more than electrons, so that all electron-hole pairs cannot be fully utilized. , so that the efficiency and service life of the device are reduced

Method used

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  • A kind of carboline trisubstituted derivative and its application
  • A kind of carboline trisubstituted derivative and its application
  • A kind of carboline trisubstituted derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of Compound A1

[0046] 6 g α-carboline, 8.5 g 1,3,5-tribromobenzene, 14 g potassium carbonate, 0.7 g cuprous iodide, 120 ml N,N-dimethylformamide, under nitrogen protection, reflux reaction 24h. After the completion of the reaction, suction filtration, the filtrate was extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 4.5 g of solid with a yield of 67%. Mass spectrum: theoretical m / e, 576.2; found 576.1.

[0047]

Embodiment 2

[0048] Example 2: Preparation of Compound A7

[0049] 6 g of δ-carboline, 8.5 g of 2,4,6-tribromopyridine, 14 g of potassium carbonate, 0.7 g of cuprous iodide, 120 ml of N,N-dimethylformamide, under nitrogen protection, reflux reaction 24h. After the completion of the reaction, suction filtration, the filtrate was extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 5.8 g of solid with a yield of 85%. Mass spectrum: theoretical m / e, 577.6; found 577.5.

[0050]

Embodiment 3

[0051] Example 3: Preparation of Compound B4

[0052]

[0053]a) Synthesis of N-(3-bromophenyl)-δ-carboline: combine 2 g of δ-carboline, 8.5 g of m-dibromobenzene, 14 g of potassium carbonate, 0.7 g of cuprous iodide, 50 ml of N, N-dimethylformamide, under nitrogen protection, refluxed for 24h. After the reaction was completed, suction filtration, the filtrate was extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 2.0 g of solid with a yield of 54%. Mass spectrum: theoretical m / e, 323.2; found 323.2. 1 H-NMR (500MHz, CDCl 3 ): 8.62(1H), 8.44(1H), 7.74-7.68(2H), 7.62(1H), 7.56-7.44(4H), 7.39(1H), 7.33(1H).

[0054] b) Synthesis of 3-(δ-carbolinyl)-phenylboronic acid pinacol ester: combine 5 g of N-(3-bromophenyl)-δ-carboline, 5 g of biboronate, 5 g of acetic acid Potassium, 0.3 g PdCl 2 (PPh 3 ) 2 , 150 ml of 1,4-dioxane was added to the three-necked flask, under nitrogen protection, refluxe...

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Abstract

The invention discloses a carboline tri-substituted derivative and an application thereof. Its general structural formula is: in the formula, X 1 , X 2 Can be independently selected from one of C and N, and only one is N atom; R is selected from hydrogen atom, halogen atom, alkyl group, substituted alkyl group, cyano group, amino group, substituted amino group, substituted silyl group, phenyl group, naphthalene aryl, any one of substituted or unsubstituted aryl, biaryl, fused-ring aryl, substituted or unsubstituted nitrogen-containing heterocyclic aryl, and benzoheterocyclic aryl; the compounds of the present invention can be applied Transport layer materials and light-emitting layer materials in organic electroluminescent devices. The present invention can be used as an electron or hole transport material, and can also be used as a light-emitting body, including being used as a light-emitting layer alone or as a host doping dye to emit light, or forming an exciplex with other materials to emit light; the present invention is used for organic electrophoresis The triplet energy of the light-emitting body is high, and the electron and hole transport capabilities of the host material are balanced, so that the efficiency of the light-emitting device is high.

Description

technical field [0001] The present invention relates to the technical field of carboline derivatives, in particular to a carboline trisubstituted derivative and its application. Background technique [0002] Due to the continuous development of the display industry, the requirements for flat panel display products are getting higher and higher, and the current display technology is mainly divided into three types: plasma display, field emission display and organic electroluminescence display (OLED). Among them, organic electroluminescent diodes have advantages such as self-luminescence, no need for backlight, high contrast, thin thickness, wide viewing angle, fast response speed, flexible panels, wide operating temperature range, and simple structure and process. It is considered to be the next-generation flat-panel display emerging application technology. [0003] In 1987, C. W. Tang et al. of KODAK Company in the United States adopted the evaporation technology, using ITO...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C09K11/06
CPCC09K11/06C07D519/00C09K2211/1059C09K2211/1044C09K2211/1029
Inventor 王子兴吴鹏沈博文王荷丹赵晓宇
Owner ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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