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Compound of quinacridones-carbazole group and application in organic electroluminescence device

A technology of quinacridone and carbazole, which is applied in organic electroluminescent materials and its application fields, can solve the problems of fluorescence quenching and strict device process requirements, and achieve good stability, convenient purification, and electroluminescence efficiency high effect

Inactive Publication Date: 2007-02-14
吉林吉大瑞博光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The electroluminescent devices prepared by the quinacridone derivatives used by Murayama et al. and Shi Jianmin etc. have obtained good performance devices, but because the quinacridone derivative light-emitting compound molecules used are relatively easy to aggregate, it must be processed in a very short time. Higher efficiency can only be achieved at a low doping concentration (less than 1%). Higher concentration will lead to fluorescence quenching, which makes the device evaporation process very strict. When mass production, the device process is very demanding, so Finding materials that can achieve high-efficiency electroluminescence in a wide concentration range is an urgent problem to be solved
In addition, the electroluminescent efficiency of quinacridone derivatives used by Murayama et al. and Shi Jianmin et al. needs to be further improved.

Method used

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  • Compound of quinacridones-carbazole group and application in organic electroluminescence device
  • Compound of quinacridones-carbazole group and application in organic electroluminescence device
  • Compound of quinacridones-carbazole group and application in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] Example 1: Synthesis of TMDCzBQA

[0028] Compound 2,5-dihydroxy-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester 5.0g, 3,5-dimethylaniline 10ml, hydrochloric acid 0.5ml, heat to reflux with ethanol as solvent 6 hours. Cool and filter, wash the precipitate with ethanol to obtain 8.2 grams of pink product 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylate diethyl ester, Yield 90.3%.

[0029] Compound 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylate 5.0 g and 1-chloronaphthalene were heated to reflux at 260°C for 2 hours, filtered and washed with chloroform to obtain 3.2 g of the product 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone with a yield of 81.2%.

[0030] Add 2.5 grams of compound 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone into nitrobenzene, potassium hydroxide, and ethylene glycol monomethyl ether, heat and reflux for 2 hours, and then add 100ml of ethanol and 150ml of acetic acid were heated to reflux for 2 hours, ...

example 2

[0036] Example 2: Synthesis of TMDCzHQA

[0037] The synthesis of TMDCzHQA is the same as Example 1, just replace 1,4-dibromobutane with 1,6-dibromohexane to obtain product 1,3,8,10-tetramethyl-5,12-two {4 -N-carbazolyl)hexyl}quinacridone (TMDCzHQA). Mass spectrum molecular ion peak: 886.5. Elemental analysis according to chemical formula C 61 h 66 N 4 o 2 Calculated: C: 82.6%; H: 7.5%; N: 6.3%; found: C: 82.6%; H: 7.2%; N: 6.5%.

example 3

[0038] Example 3: Synthesis of TMDCzOQA

[0039] The synthesis of TMDCzOQA is the same as example 1, just replace 1,4-dibromobutane with 1,8-dibromooctane to obtain product 1,3,8,10-tetramethyl-5,12-two {4 -N-carbazolyl)octyl}quinacridone (TMDCzOQA). Mass spectrum molecular ion peak: 942.6. Elemental analysis according to chemical formula C 65 h 74 N 4 o 2 Calculated: C: 82.8%; H: 7.9%; N: 5.9%; found: C: 82.6%; H: 7.8%; N: 6.0%.

[0040]

[0041] 1,3,8,10-Tetramethyl-5,12-bis- 1,3,8,10-Tetramethyl-5,12-bis-(4-N-carbazolyl)-hexyl)quinacridone (4-N-carbazolyl- octyl)quinacridone

[0042] TMDCzHQA TMDCzOQA

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Abstract

A quiacridone-carbazole compound is disclosed. It can be used to prepare the organic electroluminescent device with one or more active layers, especially the green-light device.

Description

technical field [0001] The invention relates to an organic electroluminescent material and its application, in particular to a quinacridone-carbazole compound and its application as a luminescent material in an organic electroluminescent device. Background technique [0002] The phenomenon of organic electroluminescence has been discovered for more than 30 years. Before 1987, the application of organic electroluminescence devices was limited due to the huge defects (turn-on voltage>200V). In the past ten years, due to continuous breakthroughs in materials and device technology, organic electroluminescence has reached or is close to the practical stage. [0003] In 1965, Gurnee et al first published a patent on organic electroluminescent devices (U.S. Pat. No. 3,172,862, 3,173,050). In 1973, Dresner also published a patent on organic electroluminescent devices (U.S. Pat. No. 3,170,167). Polyaromatic ring organic compounds such as anthracene, tetracene, pentacene, etc. ar...

Claims

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Application Information

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IPC IPC(8): C07D471/04H05B33/14C07D221/00
Inventor 王悦霍成边航叶开其
Owner 吉林吉大瑞博光电科技有限公司
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