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Organic electrophosphorescent material and its preparation method and application

A compound and fluorine atom technology, applied in the field of organic electrophosphorescent materials and their preparation, can solve the problems of small luminescence contribution and difficulty in improving luminous efficiency, etc.

Active Publication Date: 2016-04-13
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 prohibition effect of quantum statistics, triplet excitons mainly undergo non-radiative attenuation, which contributes very little to luminescence, and only singlet excitons 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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  • Organic electrophosphorescent material and its preparation method and application
  • Organic electrophosphorescent material and its preparation method and application
  • Organic electrophosphorescent material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Example 1. Preparation of Compound GIR-AC-I-001 (Method 1)

[0139]

[0140] 1.0g (0.5mmol) of compound G-2, 98mg (1mmol) of acetylacetone and 519mg (5mmol) of anhydrous sodium carbonate were dispersed in 40ml of acetonitrile and 40ml of chloroform, under the protection of nitrogen, the temperature was refluxed to carry out the substitution reaction After 24 hours, cool to room temperature, pour the reaction solution into water, extract with DCM, dry the organic phase, filter, concentrate the filtrate to dryness under reduced pressure, and separate and purify the residue through a silica gel column to obtain 650 mg of compound GIR-AC-I-001. yellow solid.

[0141] Experimental data:

[0142] (1) 1 HNMR (δ, CDCl 3 ): 0.08~0.10 (1H, m); 0.12~0.18 (3H, m); 0.53~0.58 (1H, d); 0.73~0.90 (10H, m); 0.96~1.42 (15H, m); 1.64~1.78 (5H, m); 6.58-6.65 (1H, q); 6.96-7.01 (1H, t); 7.75-7.79 (1H, t); 8.21-8.33 (2H, m). It is confirmed that the substance obtained by the reaction...

Embodiment 2

[0146] Example 2, Preparation of Compound GIR-AC-II-001 (Method 3)

[0147]

[0148] Stir and disperse 1.08g of the compound shown in G-2 and 3.97g of the compound shown in G-1 with 50ml of glycerin. Under the protection of nitrogen, raise the temperature to 180°C, stir for 8 hours for substitution reaction, cool to room temperature, pour the reaction solution into 200ml 1N dilute hydrochloric acid, filter with suction, wash the filter cake with water, separate and purify the obtained solid with a silica gel column to obtain 0.66 g of GIR-AC-I-001 as a white solid.

[0149] Experimental data:

[0150] (1) 1 HNMR (δ, CDCl 3 ): 0.11~0.18 (3H, m); 0.85~1.92 (20H, m); 2.43 (2H, m); 3.69 (2H, m); 6.58~6.65 (1H, q); ); 7.75~7.79 (1H,t); 8.21~8.33 (2H,m). It is confirmed that the substance obtained by the reaction is indeed the compound GIR-AC-II-001;

[0151] (2) Glass transition temperature (DSC): /

[0152] (3) UV maximum absorption wavelength (DCM): 325nm, 378nm;

[015...

Embodiment 3

[0154] Preparation of Example 3 Compound GIR-AP-I-001 (Method 2)

[0155]

[0156] 2.04g of compound G-2 and 707mg of 2-pyridinecarboxylic acid, 324mg of anhydrous potassium carbonate and 50ml of 1,4-dioxane were heated and refluxed to carry out the substitution reaction for 8 hours, concentrated to dryness under reduced pressure, and the residue was washed with silica gel Column separation and purification yielded 1.1 g of compound GIR-AP-I-001 as a yellow solid.

[0157] Experimental data:

[0158] (1) 1 HNMR (δ, CDCl 3 ): 0.12~0.18 (6H, m); 0.84~1.94 (40H, m); 2.45 (4H, m); 3.71 (4H, m); 6.58~6.68 (2H, q); ); 7.65~7.79 (6H,t); 8.21~8.49 (4H,m). It is confirmed that the substance obtained by the reaction is indeed the compound GIR-AP-I-001;

[0159] (2) glass transition temperature (DSC): / ;

[0160] (3) UV maximum absorption wavelength (DCM): 248nm, 311nm, 378nm;

[0161] (4) Phosphorescence emission wavelength (DCM): 445nm, 510nm.

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Abstract

The invention discloses an organic electro-generated phosphor luminescent material as well as a preparation method and application thereof. The organic electro-generated phosphor luminescent material has a structural formula as shown in a formula I. Based on the electro-generated phosphor luminescent material which needs good film-forming performance and a shorter phosphorescence service life, and improves luminous efficiency and performance of luminescent devices at the same time, the invention provides a series of iridium or platinum compound electro-generated phosphor luminescent materials with chiral groups. The compounds have characteristics of excellent film-forming performance, high luminous efficiency and the like; moreover, materials are easily available, preparation is simple, overall yield is high, the cost of the phosphor luminescent material is greatly lowered, and application value is important.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and relates to an organic electroluminescent material, a preparation method and application thereof. Background technique [0002] 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 ...

Claims

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Application Information

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