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 t

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 Embodiment

[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, heated to reflux with ethanol as solvent 6 hours. Cool and filter, wash the precipitation with ethanol to obtain 8.2 g of pink product 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylate diethyl ester, Yield 90.3%.

[0029] The compound 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester 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] 2.5 g of compound 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone was added to nitrobenzene, potassium hydroxide, ethylene glycol monomethyl ether, heated to reflux for 2 hours, and then added 100 ml of ethanol and 150 ml of acetic acid were heated ...

Example Embodiment

[0036] Example 2: Synthesis of TMDCzHQA

[0037] The synthesis of TMDCzHQA is the same as in Example 1, except that 1,6-dibromohexane is used instead of 1,4-dibromobutane to obtain the product 1,3,8,10-tetramethyl-5,12-bis{4 -N-carbazolyl)hexyl}quinacridone (TMDCzHQA). Mass spectrum molecular ion peak: 886.5. Elemental analysis according to formula C 61 H 66 N 4 O 2 Calculated: C: 82.6%; H: 7.5%; N: 6.3%; Experiment: C: 82.6%; H: 7.2%; N: 6.5%.

Example Embodiment

[0038] Example 3: Synthesis of TMDCzOQA

[0039] The synthesis of TMDCzOQA is the same as in Example 1, except that 1,8-dibromooctane is used instead of 1,4-dibromobutane to obtain the product 1,3,8,10-tetramethyl-5,12-bis{4 -N-carbazolyl)octyl}quinacridone (TMDCzOQA). Mass spectrum molecular ion peak: 942.6. Elemental analysis according to formula C 65 H 74 N 4 O 2 Calculated: C: 82.8%; H: 7.9%; N: 5.9%; Experiment: 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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