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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AI-Extracted 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...
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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.

Application Domain

Technology Topic

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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(64)

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 to reflux for 2 hours, and the product was filtered by washing with water, ethanol and chloroform to obtain a red product. 1,3,8,10-Tetramethylquinacridone (TMQA) 2.1 g Yield 84.5%.
[0031]
[0032] 1,3,8,10-Tetramethyl-5,12-bis-(4-N-carbazolyl-butyl)quinacridone
[0033] TMDCzBQA
[0034] The above TMQA was added to the tetrahydrofuran solvent, 2.0 ml of 1,4-dibromobutane and a little sodium hydride were added, and the reaction was heated under reflux for 12 h. Cool, add appropriate amount of methanol and let stand. After filtration, an orange-red solid, 1,3,8,10-tetramethyl-5,12-bis(4-bromobutyl)quinacridone, was precipitated with petroleum ether, the product was 2.0 g, and the yield was 50%.
[0035] 1.05 g of carbazole was reacted with the above 1,3,8,10-tetramethyl-5,12-bis(4-bromobutyl)quinacridone in the presence of a little KOH in butanone under reflux for 12h . Cool, wash with water, and extract with dichloromethane. with Al 2 O 3 As the stationary phase, cyclohexane is used as the developing solvent to run the chromatographic column to obtain a red powdery solid product 1,3,8,10-tetramethyl-5,12-bis{4-N-carbazolyl)butyl}quinoline Acridone (TMDCzBQA) 0.76 g, 30% yield. Mass spectrum molecular ion peak: 830.5. Elemental analysis according to formula C 57 H 58 N 4 O 2 Calculated: C: 82.4%; H: 7.0%; N: 6.7%; Experiment: C: 82.6%; H: 7.2%; N: 6.5%.

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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PUM

PropertyMeasurementUnit
Shine35.0m
Shine36.0m
Shine535.0nm
tensileMPa
Particle sizePa
strength10

Description & Claims & Application Information

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