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Liquid crystal modified carbazole derivative organic electrophosphorescent materials as well as preparation method and application thereof

A reaction and compound technology, applied in the field of carbazole derivative organic electrophosphorescent materials and its preparation, can solve the problems of lack of stability and efficiency

Inactive Publication Date: 2015-03-25
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently known materials with practical value and potential are still very limited, especially organic materials with excellent comprehensive indicators are urgently needed to be researched and developed. Among them, although green phosphorescent materials are basically suitable for commercial use, they are still lacking in stability and efficiency.

Method used

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  • Liquid crystal modified carbazole derivative organic electrophosphorescent materials as well as preparation method and application thereof
  • Liquid crystal modified carbazole derivative organic electrophosphorescent materials as well as preparation method and application thereof
  • Liquid crystal modified carbazole derivative organic electrophosphorescent materials as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Embodiment 1, the preparation of compound RIr-AC-I-001 (method one)

[0128]

[0129] The acetylacetone of the compound G-2 of 1.406g (1mmol) and 192mg (2mmol) and the anhydrous sodium carbonate of 1.038g (10mmol) are dispersed in the acetonitrile of 80ml and the chloroform of 80ml, under the protection of nitrogen, temperature rises and refluxes and carries out substitution reaction After 24 hours, cool to room temperature, pour the reaction solution into water, extract with DCM, dry the organic phase, filter, and concentrate the filtrate to dryness under reduced pressure. The residue is separated and purified by silica gel column to obtain 650 mg of compound RIr-AC-I-001, yellow solid;

[0130] Experimental data:

[0131] (1) 1HNMR (δ, C2D6SO): 0.8~1.0(23H,m); 1.0~1.3(10H,m); 1.3~1.7(15H,d); 1.7~2.0(7H,m); 3.2~3.5( 6H,m); 5.2~5.5(1H,m); 6.0~6.2(2H,q); 6.2~6.5(4H,t); 7.0~7.2(2H,t); 7.2~7.8(15H,m). It is confirmed that the substance obtained by the reaction is ind...

Embodiment 2

[0136] Embodiment 2, the preparation of compound RIr-AC-II-001 (method three)

[0137]

[0138] Stir and disperse 1.4g of the compound shown in G-2 and 4.76g of the compound shown in G-1 with 80ml of glycerin. Under nitrogen protection, heat up to 180°C, stir and reflux for substitution reaction for 8 hours, cool to room temperature, and dissolve the reaction solution Pour into 200ml of 1M dilute hydrochloric acid, suction filter, wash the filter cake with water, separate and purify the obtained solid with silica gel column to obtain 0.84g of RIr-AC-I-001 as a white solid.

[0139] Experimental data:

[0140] (1) 1HNMR (δ, C2D6SO): 0.8~1.0(35H,m); 1.0~1.3(15H,m); 1.3~1.7(21H,d); 1.7~2.0(11H,m); 6.0~6.2( 5H,q); 6.2~6.5(7H,t); 7.0~7.2(3H,t); 7.2~7.8(20H,m). It is confirmed that the substance obtained by the reaction is indeed the compound RIr-AC-II-001;

[0141] (2) Glass transition temperature (DSC): 264.3°C;

[0142] (3) UV maximum absorption wavelength (DCM): 256nm, 31...

Embodiment 3

[0145] Embodiment 3, the preparation of compound RIr-AP-I-001 (method two)

[0146]

[0147] 2.8g 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 1.4 g of compound RIr-AP-I-001 as a yellow solid.

[0148] Experimental data:

[0149] (1) 1HNMR (δ, C2D6SO): 0.8~1.0(23H,m); 1.0~1.3(10H,m); 1.3~1.7(15H,d); 1.7~2.0(7H,m); 3.2~3.5( 6H,m); 5.2~5.5(2H,m); 6.0~6.2(3H,q); 6.2~6.5(5H,t); 6.6~6.8(2H,m)7.0~7.2(3H,t); 7.2 ~7.8(17H,m). It is confirmed that the substance obtained by the reaction is indeed the compound RIr-AP-I-001;

[0150] (2) Glass transition temperature (DSC): 268.6°C;

[0151] (3) UV maximum absorption wavelength (DCM): 258nm, 307nm, 324nm;

[0152] (4) Phosphorescence emission waveleng...

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Abstract

The invention discloses liquid crystal modified carbazole derivative organic electrophosphorescent materials as well as a preparation method and application thereof. A structural general formula of the materials is shown in a formula I in the specification. The invention provides a series of iridium or platinum complex electrophosphorescent materials with chiral groups because efficient electrophosphorescent materials with good film-forming properties and shorter phosphorescence lifetime are needed and in order that the luminescent efficiency and the properties of luminescent devices are improved at the same time. The compounds have the characteristics of excellent film-forming properties, high luminescent efficiency, and the like, are accessible in raw materials, are simple and convenient to prepare, have high total yields, have the effect of greatly reducing the costs of phosphorescent materials and have important application values.

Description

technical field [0001] The invention belongs to the field of liquid crystals, and relates to a liquid crystal modified carbazole derivative organic electrophosphorescent material and a preparation method and application thereof. 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, 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 lig...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D235/18C09K11/06H01L51/54
CPCC09K11/06C07D235/18C07F15/0033C09K2211/1044C09K2211/185H10K85/342H10K50/11
Inventor 王士波曹建华黄红亮贾磊磊逄辉
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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