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Series organic electrophosphorescent material

A compound and selected technology, applied in the fields of luminescent materials, organic chemistry, circuits, etc., can solve the problems of small luminous contribution and difficult to improve luminous efficiency.

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

[0089] The preparation of embodiment 1 compound PHIR-AC-005

[0090]

[0091] Step 1: Preparation of 6,6′-difluorobiphenyl-2,2′-dicarboxylic acid

[0092]

[0093] Dissolve 75g of copper sulfate pentahydrate in 300ml of water, add 230ml of 25% ammonia water under stirring, and cool down to 0°C with an ice-salt bath. An aqueous solution prepared by 20.8 g of hydroxylamine hydrochloride and 12.8 g of sodium hydroxide was slowly added dropwise into the above cold copper solution, and kept below 0° C. for later use.

[0094] Mix 31g of 2-amino-3-fluorobenzoic acid and 85ml of concentrated hydrochloric acid, add 300ml of water and 60ml of acetonitrile, and cool down to below 0°C with an ice-salt bath, slowly drop the solution of 15.9g of sodium nitrite dissolved in 120ml of water Add to the above solution, stir and react at below 5°C for 1 hour, slowly add this clear diazonium solution dropwise into the reserved copper solution, and keep the temperature below 10°C during thi...

Embodiment 2

[0127] The preparation of embodiment 2 compound PHIR-AC-006

[0128]

[0129] The first step: preparation of compound G-2

[0130]

[0131] 1.0g of compound 2-(4,5-bistrifluoromethyl-9,10-dihydrophenanthrene-2-yl)pyridine (refer to Example 1, the synthesis of the first to eight steps) and 427mg of IrCl 3 ·3H 2 O was dispersed in 30ml of ethylene glycol ether and 10ml of water, under the protection of nitrogen, the temperature was raised to reflux for 24 hours, cooled to room temperature, filtered, the filter cake was washed with water, and dried in vacuo to obtain 520mg of compound G-2 as a yellow solid.

[0132] The second step: the preparation of compound PHIR-AC-006

[0133]

[0134] 500mg of compound G-2, 62mg of acetylacetone and 262mg of anhydrous sodium carbonate were dispersed in 40ml of ethylene glycol ether, under the protection of nitrogen, the temperature was raised to reflux for 24 hours, cooled to room temperature, and the reaction solution was poured ...

Embodiment 3

[0140] The preparation of embodiment 3 compound PHIR-AC-001

[0141]

[0142] The first step: the preparation of 2-(4,5-difluorophenanthrene-2-yl)pyridine

[0143]

[0144] 1.5g of 2-(4,5-difluoro-9,10-dihydrophenanthrene-2-yl)pyridine prepared in the eighth step of Example 1 was dissolved in 100ml of benzene, 3.5g of DDQ was added, and heated to reflux for reaction After 3 days, it was cooled to room temperature, concentrated to dryness under reduced pressure, and the residue was separated and purified by a neutral alumina column to obtain 1.4 g of 2-(4,5-difluorophenanthrene-2-yl)pyridine as a white solid.

[0145] The second step: the preparation of compound G-2

[0146]

[0147] Referring to the ninth step of Example 1, replace 2-(4,5-difluoro-9,10-dihydrophenanthrene-2-yl)pyridine with 2-(4,5-difluorophenanthrene-2-yl ) pyridine to obtain compound G-2, a yellow solid.

[0148] The third step: preparation of compound PHIR-AC-001

[0149]

[0150] Referring ...

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Abstract

The invention discloses a series organic electrophosphorescent material. A structural general formula of the electrophosphorescent material is shown as a formula I. The complex electrophosphorescent luminescent material takes 4,5-disubstituted phenanthrene and 4,5-disubstituted 9, 10-dihydrophenanthrene as a main body. Due to influence of electron donating group with 4,5-two large steric hindrance, fixing effect of phenanthrene and 9,10- dihydrophenanthrene hydrocarbon chain, the capture capability to exciton is greatly increased, phosphorescence life can be effectively shortened, the luminescence efficiency is increased, and the luminescent device performance is increased. The compound has excellent film forming ability and high luminescence efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display and relates to a series of organic electroluminescent materials. 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, deve...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D213/26C07D213/16C07D213/30C07D213/127C09K11/06H01L51/54
Inventor 曹建华华瑞茂郭剑李雅敏
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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