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Compound containing pyrazole structural unit

A compound, pyridyl-based technology, applied in the field of organic electroluminescence display, can solve problems such as difficulty in improving luminous efficiency and small luminous contribution

Active Publication Date: 2014-07-23
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, the generation ratio of singlet excitons and triplet excitons is 1:3, and according to the forbidden effect of quantum prohibition, triplet excitons mainly undergo non-radiative attenuation, which contributes very little to luminescence, and only singlet excitons radiate Therefore, for organic / polymer electroluminescent devices, the fundamental reason why the luminous efficiency is difficult to improve is that the luminescence process is the luminescence of singlet excitons

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] The preparation of embodiment 1 compound DPYIR-AC-001

[0092]

[0093] The first step: the preparation of (E)-3-(dimethylamino)-1-(pyridin-2-yl)propen-1-one

[0094]

[0095] Dissolve 12.1 g of 2-acetylpyridine in 150 ml of toluene, add 30 ml of DMF-DMA under stirring, heat and reflux for 24 hours, cool to room temperature, concentrate to dryness under reduced pressure, add 150 ml of petroleum ether to the residue, stir Disperse, filter, and wash the filter cake with petroleum ether to obtain 13 g of the intermediate as yellow crystals.

[0096] The second step: the preparation of 2-(1-(4-fluorophenyl)-1H-pyrazol-3-yl)pyridine

[0097]

[0098] Mix 5g of CJH-1 and 3.6g of 4-fluorophenylhydrazine, add 80ml of ethanol, add reflux reaction for 12 hours, cool to room temperature, concentrate to dryness under reduced pressure, the residue is separated and purified by silica gel column, ethyl acetate and petroleum ether Elution yielded 6.6 g of CJH-2 as a red soli...

Embodiment 2

[0110] The preparation of embodiment 2 compound DPYPT-AC-015

[0111]

[0112] The first step: the preparation of 4-hydrazinopyridine hydrochloride

[0113]

[0114] Mix 3.0 g of 4-chloropyridine hydrochloride with 20 ml of 85% hydrazine hydrate and 20 ml of ethanol, heat to reflux for 24 hours, cool to room temperature, concentrate 1 / 2 under reduced pressure, add 20 ml of water to dilute, and dilute with ethyl acetate / The THF mixed solution was extracted, the organic phase was dried, concentrated to dryness under reduced pressure, 50 ml of petroleum ether was added to the residue, frozen and crystallized, and the precipitate was filtered to obtain a yellow solid.

[0115] The second step: the preparation of compound CJH-2

[0116]

[0117] Mix 5.0 g of the compound CJH-1 prepared in Example 1 with 3.1 g of 4-hydrazinopyridine, add 80 ml of ethanol, heat to reflux for 12 hours, cool to room temperature, concentrate to dryness under reduced pressure, and separate the...

Embodiment 3

[0129] The preparation of embodiment 3 compound DPYIR-DPY-001

[0130]

[0131]768mg of DPYIR-AC-001 and 480mg of the compound CJH-2 prepared in the second step of Example 1 were stirred and dispersed with 20ml of glycerin. Under the protection of nitrogen, the temperature was raised to 180°C, stirred for 8 hours, cooled to room temperature, and the The solution was poured into 100ml of 1N dilute hydrochloric acid, suction filtered, the filter cake was washed with water, and the obtained solid was separated and purified by a silica gel column to obtain 460 mg of DPYIR-DPY-001 as a brown solid.

[0132] Experimental data:

[0133] 1 H NMR (CDCl 3 ,300MHz):δ=8.27-8.34(m,4H),8.14-8.16(d,2H),7.87-7.90(m,2H),7.53-7.56(m,4H),7.22-7.26(m,4H) ,7.06-7.10(m,2H).

[0134] (1) Glass transition temperature (DSC): 286.35°C;

[0135] (2) UV maximum absorption wavelength (DCM): 250nm, 280nm, 295nm;

[0136] (3) Phosphorescence emission wavelength (DCM): 616nm.

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Abstract

The invention discloses a compound containing a pyrazole structural unit. A structural general formula of the compound is shown as a formula I. Because that an electrophosphorescent material requires good film-forming performance and a high-efficiency phosphorescence material having short phosphorescence life, by aiming at enhancement of luminescence efficiency and luminescent device performance, the invention provides a series of electrophosphorescent materials of iridium or platinum complex having pyrazole group. The compound has excellent film forming ability and high luminescence efficiency, the raw material is easily available, the compound is simple to prepare, the total yield is high, the cost of phosphorescence material is greatly reduced, and the compound has important application value.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and relates to a compound containing a pyrazole structural unit. Background technique [0002] For organic electroluminescence (referred to as OLED) and related research, as early as 1963, Pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display. And other advantages, can be widely used in flat panel displays and surface light sources, so it has been widely researched, dev...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D401/04C07D401/14C07D405/14C07D409/14C09K11/06H01L51/54
Inventor 曹建华华瑞茂郭剑李雅敏
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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