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Quinacridone derivant and application in organic electroluminescent device thereof

A quinacridone and derivative technology, applied in the field of organic electroluminescent materials, can solve the problems of harsh device process requirements, fluorescence quenching, etc., and achieve the effects of good stability, low turn-on voltage and high luminous efficiency

Active Publication Date: 2004-03-17
JILIN UNIV
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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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  • Quinacridone derivant and application in organic electroluminescent device thereof
  • Quinacridone derivant and application in organic electroluminescent device thereof
  • Quinacridone derivant and application in organic electroluminescent device thereof

Examples

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example 1

[0024] The following examples are used to further illustrate the preparation and application of the compounds of the present invention, instead of limiting the present invention by using these examples. Example 1: Synthesis of HMQA

[0025] Using 120ml of absolute ethanol as solvent, add 10.0g of compound 2,5-dihydroxy-1,4-cyclohexadiene-1,4-dicarboxylate, 20ml of 3,5-dimethylaniline, and hydrochloric acid 1ml, heated to reflux for 6 hours. Cool and filter, wash the precipitate with ethanol to obtain 16.3 g of pink product 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester, The yield was 90.3%.

[0026] 10.0 g of the compound 2,5-bis(3,5-dimethylanilino)-1,4-cyclohexadiene-1,4-dicarboxylic acid diethyl ester and 1-chloronaphthalene were heated to reflux at 260°C 2 After hours, filter and wash with chloroform, 6.5 g of 1,3,8,10-tetramethyl-6,13-dihydro-quinacridone is obtained, and the yield is 81.2%.

[0027] Add 5.0 g of compound 1,3,8,10-tetramet...

example 2

[0031] HMQA Example 2: Synthesis of TMDEQA

[0032] The synthesis of TMDEQA is the same as in Example 1. Only bromoethane is used instead of methyl iodide. The product 1,3,8,10-tetramethyl-5,12-diethylquinacridone (TMDEQA). Mass spectrum molecular ion peak: 425. Elemental analysis according to chemical formula C 28 H 28 N 2 O 2 Calculation: C: 79.2%; H: 6.6%; N: 6.6%; experimental value: C: 79.1%; H: 6.8%; N: 6.5%.

[0033]

[0034] 5,12-Diethyl-1,3,8,10-tetramethyl-quinacridone

example 3

[0035] TMDEQA Example 3: Synthesis of TMDPQA

[0036] The synthesis of TMDPQA is the same as in Example 1. Only 1-bromopropane is used instead of methyl iodide. The product 1,3,8,10-tetramethyl-5,12-dipropylquinacridone (TMDBA). Mass spectrum molecular ion peak: 453. Elemental analysis according to chemical formula C 30 H 32 N 2 O 2 Calculation: C: 79.6%; H: 7.1%; N: 6.2%; experimental value: C: 79.3%; H: 7.3%; N: 6.0%.

[0037]

[0038] 1,3,8,10-Tetramethyl-5,12-dipropyl-quinacridone

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Abstract

The present invention relates to organic electroluminescent material, and is especially one kind of quinacridone derivative and its application as electroluminescent material. One series of hexasubstituted quinacridones as novel electroluminescent material for producing high performance organic electroluminescent device is provided. The organic electroluminescent device of the present inventionconsists of glass substrate, positive electrode, negative electrode, carrier implanting layer between the positive electrode and the negative electrode, carrier transmission layer and luminescence layer. The compound of the present invention plays important role in the luminescence layer. The compound of the present invention has simple preparation process, and the luminescent device has high brightness, high efficiency, efficiency less affected by the dope density, low start voltage, long life and other advantages.

Description

Technical field [0001] The invention relates to an organic electroluminescence material, in particular to a quinacridone derivative and its application in an organic electroluminescence device. Background technique [0002] Organic electroluminescence has been discovered for more than 30 years. Before 1987, due to the huge defects of organic electroluminescence devices (opening voltage>200V), its application was limited. In the past ten years, due to continuous breakthroughs in materials and device technology, organic electroluminescence has reached or approached the practical stage. [0003] In 1965, Gurnee et al. first published patents on organic electroluminescent devices (U.S. Pat. No. 3,172,862, 3,173,050). Dresner also published a patent on organic electroluminescent devices in 1973 (U.S. Pat. No. 3,170,167). In these inventions, polyaromatic organic compounds such as anthracene, tetraacene, pentacene, etc. are used as organic electroluminescent materials. The main stru...

Claims

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Application Information

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IPC IPC(8): C07D401/10H05B33/22
Inventor 王悦叶开其刘宇吴英
Owner JILIN UNIV
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