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Orange phosphorescent oled material

An aromatic group and substituent technology, applied in the field of organic electroluminescence display, can solve the problems of difficult to improve luminous efficiency and small luminous contribution

Active Publication Date: 2016-06-08
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

[0107] Example 1 Preparation of compound DPYIR-AC-001

[0108]

[0109] 1.4g of compound CJH-5, 200mg of acetylacetone and 424mg of anhydrous sodium carbonate were dispersed in 40ml of ethylene glycol ether / acetonitrile. Under the protection of nitrogen, the reaction was heated and refluxed for 24 hours, cooled to room temperature, and the reaction solution was poured. It was poured into water, extracted with DCM, the organic phase was dried, filtered, the filtrate was concentrated under reduced pressure to dryness, and the residue was separated and purified by silica gel column to obtain 950 mg of compound DPYIR-AC-001 as a brown solid.

[0110] Experimental data:

[0111] 1 HNMR(CDCl 3 ,300MHz): δ=8.28-8.34(m,4H),8.13-8.14(d,2H),7.86-7.91(t,2H),7.52-7.55(m,4H),7.21-7.25(m,4H) , 7.07-7.11 (t, 2H), 5.01 (s, 1H), 1.64 (s, 6H).

[0112] (1) Glass transition temperature (DSC): 287.98℃;

[0113] (2) UV maximum absorption wavelength (DCM): 275nm, 285nm, 295nm;

[0114] (3) Phosphorescence e...

Embodiment 2

[0115] Example 2 Preparation of compound DPYPT-AC-015

[0116]

[0117] Take 1.0g of CJH-5b, 225mg of acetylacetone and 470mg of anhydrous sodium carbonate and disperse in 40ml of ethylene glycol ether. Under the protection of nitrogen, heat up and stir for 24 hours at 100℃, cool to room temperature, filter, filter cake Wash with water, then dissolve with DCM, filter, dry the filtrate, filter, and concentrate the filtrate to dryness under reduced pressure to obtain 650 mg of compound DPYPT-AC-015 as a red solid.

[0118] Experimental data:

[0119] 1 HNMR(CDCl 3 ,300MHz): δ=8.30-8.36(m,3H), 8.14-8.17(m,2H),7.84-7.87(m,2H),7.52-7.55(m,2H),5.00(s,1H),1.66 (s,6H).

[0120] (1) Glass transition temperature (DSC): 264.87℃;

[0121] (2) UV maximum absorption wavelength (DCM): 275nm, 285nm, 305nm;

[0122] (3) Phosphorescence emission wavelength (DCM): 618nm.

Embodiment 3

[0123] Example 3 Preparation of compound DPYIR-DPY-001

[0124]

[0125] 768mg of DPYIR-AC-001 and 480mg of compound CJH-2, stirred and dispersed with 20ml of glycerin, heated to 180°C under nitrogen protection, stirred for 8 hours, cooled to room temperature, poured the reaction solution into 100ml of 1N dilute hydrochloric acid In, suction filtration, washing the filter cake with water, and separating and purifying the obtained solid with a silica gel column to obtain 550 mg of DPYIR-DPY-001, a brown solid.

[0126] Experimental data:

[0127] 1 HNMR(CDCl 3 ,300MHz): δ=8.27-8.34(m,4H),8.13-8.15(d,2H),7.87-7.90(m,2H),7.53-7.56(m,4H),7.22-7.24(m,4H) ,7.06-7.10(m,2H).

[0128] (1) Glass transition temperature (DSC): 289.38℃;

[0129] (2) UV maximum absorption wavelength (DCM): 275nm, 285nm, 315nm;

[0130] (3) Phosphorescence emission wavelength (DCM): 604nm.

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Abstract

The invention discloses an orange phosphorescence OLED material. A structural general formula of the orange phosphorescence material 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 orange phosphorescence OLED material has important application value.

Description

Technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and relates to an orange phosphorescent OLED material. Background technique [0002] For organic electroluminescence (referred to as OLED) and related research, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene as early as 1963. In 1987, Kodak in the United States used the method of vapor deposition of organic small molecules to make an amorphous film device, which reduced the driving voltage to less than 20V. This kind of device has ultra-light and thin, fully cured, self-luminous, 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 soft display And other advantages, it can be widely used in flat panel displays and surface light sources, so it has been widely researched,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D401/14C09K11/06C07F15/00C07D409/14H01L51/54
Inventor 曹建华郭剑李雅敏华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD