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Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material

A technology for luminescent materials and pentaphenylene olefins, which is applied in the preparation of luminescent materials, organic compounds, organic chemistry, etc., can solve the problems of short life and low luminous efficiency, and achieve the effects of improved performance, high luminous efficiency and good application value.

Active Publication Date: 2013-04-17
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the technical problems of low luminous efficiency and short service life of existing blue light organic luminescent materials, the present invention provides a dihydropentacene-based organic luminescent material with high luminous efficiency and long service life; Preparation method and application of pentaphenylene organic luminescent material

Method used

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  • Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material
  • Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material
  • Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of compound 001

[0034] The specific synthesis route is shown in the following structural formula:

[0035]

[0036] (1) Under a nitrogen protection system, weigh 110mmol (49.3g) of 3-bromo-N-phenylcarbazole, add 300ml of freshly steamed tetrahydrofuran solution, and add dropwise n-butyllithium 7.19 at -78℃ g, react for 2 hours, then add dropwise 200ml containing 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH) two 50mmol (22.4g) of ketone in tetrahydrofuran solution, after dripping, under nitrogen protection, react at room temperature for 8 hours, add 100ml of 1M diluted hydrochloric acid, extract 3 times with 100ml of ether, separate, concentrate, use dichloromethane: Petroleum ether=1:3 recrystallized to obtain 41.2g of white intermediate N-phenyl-3-carbazolyl dihydropentacene alcohol derivatives.

[0037] (2) Take N-phenyl-3-carbazolyl dihydropentacene alcohol derivatives, add 300ml of concentrated sulfuric acid, and react a...

Embodiment 2

[0040] Example 2: Synthesis of Compound 004

[0041] The specific synthesis route is shown in the following structural formula:

[0042]

[0043] (1) Under nitrogen protection system, weigh 110mmol (28.5g) of 3-bromo-phenanthroline group, add 300ml of freshly steamed tetrahydrofuran solution, and add 7.19g of n-butyllithium dropwise at -78℃, reaction 6. Hours, then add dropwise 200ml containing 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH)dione 50mmol ( 22.4g) tetrahydrofuran solution, after dripping, under nitrogen protection, react at room temperature for 9 hours, add 100ml 1M dilute hydrochloric acid, extract 3 times with 100ml ether, separate and concentrate, use dichloromethane: petroleum ether = 1:3 recrystallization to obtain 39.4 g of a white intermediate 3-phenanthroline dihydropentacene alcohol derivative.

[0044] (2) Take 3-phenanthroline dihydropentacene alcohol derivatives, add 300ml of concentrated sulfuric acid, react at room temperature ...

Embodiment 3

[0047] Example 3: Synthesis of Compound 007

[0048] The specific synthesis route is shown in the following structural formula:

[0049]

[0050] (1) Under the protection of nitrogen, weigh 110mmol (35.5g) of 4-bromo-triarylamino group, add 300ml of freshly steamed tetrahydrofuran solution, and add 7.19g of n-butyllithium dropwise at -78℃ to react 4 hours, then add dropwise 200ml containing 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH)dione 50mmol ( 22.4g) tetrahydrofuran solution, after dripping, under nitrogen protection, react at room temperature for 9 hours, add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of ether, separate and concentrate, use dichloromethane: petroleum ether = 1:3 recrystallization to obtain 41.6 g of white intermediate triarylaminodihydropentacene alcohol derivatives.

[0051] (2) Take the triarylamine dihydropentacene alcohol derivatives, add 300ml of concentrated sulfuric acid, react at room temperature for ...

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Abstract

The invention relates to a dihydro-pentacene-olefin organic light-emitting material, a preparation method and an application of the dihydro-pentacene-olefin organic light-emitting material, and solves technical problems of low luminous efficiency and short service life of the existing blue organic light-emitting material. The material is based on a dihydro-pentacene compound which has a larger plane structure and a larger conjugated system in comparison with anthracene derivatives; and methyl and aryl substituent groups of other condensed rings are adopted, so that the performance of the dihydro-pentacene-olefin organic light-emitting material is improved well and the dihydro-pentacene-olefin organic light-emitting material is a novel high-performance electroluminescent material. The invention also provides the preparation method of the dihydro-pentacene-olefin organic light-emitting material. According to the preparation method, reaction conditions are optimized, so that a reaction solvent is changed to be an ordinary solvent, so that the operation is convenient, the purification is easy, the yield is greatly increased and the cost is lowered. The dihydro-pentacene-olefin organic light-emitting material provided by the invention is applied to the organic electroluminescent material and has high luminous efficiency.

Description

Technical field [0001] The invention belongs to the field of organic photoelectric materials, and particularly relates to a dihydropentacene olefin organic luminescent material, and a preparation method and application thereof. Background technique [0002] As a flat panel display technology, organic electroluminescent devices have many advantages such as self-luminescence, high brightness, wide viewing angle, ultra-thin, low energy consumption, fast response speed, rollability, and full-color light emission. attention. By adopting appropriate device structure, device manufacturing technology and organic materials, the performance of the organic electroluminescent device is significantly improved. For example, in terms of full-color display, high-efficiency and stable green organic electroluminescent devices have reached a practical level. Compared with green organic electroluminescent devices, blue organic electroluminescent devices cannot fully satisfy full-color displays. In...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C07D471/04C07C211/54C07C209/68C07C217/80C07C13/62C07C1/32C07C43/215C07C41/30C07C35/44C07C29/32C07C43/23H01L51/54
Inventor 马晓宇王辉李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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