Organic phosphorescent OLED materials

A technology of luminescent materials and compounds, applied in luminescent materials, organic chemistry, electrical components, etc., can solve the problems of small luminous contribution and difficulty in improving luminous efficiency

Active Publication Date: 2014-06-04
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 phosphorescent OLED materials
  • Organic phosphorescent OLED materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Preparation of Example 1 Compound CJH-IRAC-001

[0086]

[0087] The first step: preparation of compound CJH-1

[0088]

[0089] Dissolve 3.12g of 2,2'-dibromobiphenyl in 500ml of anhydrous THF, cool down to -80°C with liquid nitrogen, and slowly add 4.4ml of 2.5M n-butyllithium-hexane solution dropwise under nitrogen protection , after stirring and reacting for 30 minutes, slowly add 2.06g of 5-dibenzocycloheptenone dissolved in THF solution dropwise, after stirring and reacting for 30 minutes, rise to room temperature and stir for 1 hour, add dropwise 150ml of saturated sodium bicarbonate The aqueous solution was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 4.4 g of a light yellow liquid, which was directly used in the next reaction without purification.

[0090] The second step: the preparation of compound CJH-2

[0091]

[0092] The light yellow liquid ...

Embodiment 2

[0117] Preparation of Example 2 Compound CJH-IRAC-005

[0118]

[0119]Referring to the fourth step of Example 1, the CJH-3 prepared in the third step of Example 1 and 2-bromo-6-picoline were used to prepare compound CJH-4, and the fifth to sixth steps of Example 1 were used to synthesize CJH-IRAC- 005, yellow solid.

[0120] Experimental data:

[0121] (1) Glass transition temperature (DSC): 237.65°C;

[0122] (2) UV maximum absorption wavelength (DCM): 305nm, 335nm, 358nm;

[0123] (3) Phosphorescence emission wavelength (DCM): 522nm.

Embodiment 3

[0124] Preparation of Example 3 Compound CJH-IRPY-001

[0125]

[0126] 2.13g of the compound CJH-5 prepared in Example 1, 707mg of 2-pyridinecarboxylic acid, 324mg of potassium carbonate-free and 50ml of 1,4-dioxane were heated and refluxed for 8 hours, then concentrated to dryness under reduced pressure. , the residue was separated and purified with a silica gel column to obtain 1.1 g of compound CJH-IRPY-001 as a yellow solid.

[0127] Experimental data:

[0128] (1) Glass transition temperature (DSC): 259.22°C;

[0129] (2) UV maximum absorption wavelength (DCM): 305nm, 335nm, 358nm;

[0130] (3) Phosphorescence emission wavelength (DCM): 525nm.

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Abstract

The invention discloses a series of organic phosphorescent OLED materials. A structural general formula of the organic phosphorescent OLED materials is shown as a formula I. The materials are obtained by using 10,11-dihydrogen spirofluorene as a main body and modifying with 2-pyridyl. Due to the influence of double bonds of electron deficient groups at 10 and 11 sites, hole transportation between molecules is facilitated; and capturing capacity for excitons is greatly increased. Due to distortion of spirofluorene molecules, [pai]-[pai] overlapping space of the molecules is greatly enlarged; phosphorescence lifetime is effectively shortened; luminescence efficiency is increased; and the performance of luminescent devices is improved. A compound related by the invention has the advantages of excellent film-forming property and high luminescent efficiency. The formula I is shown as the description.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display and relates to a series of organic phosphorescent OLED materials. 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 has been widely researched, develope...

Claims

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Application Information

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Patent Type & Authority Applications(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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