Spiro-fluorene-9,9-xanthene bipolar luminescent material, its preparation method and its application method

A luminescent material, xanthene fluorene technology, applied in the manufacture of semiconductor/solid-state devices, electrical components, circuits, etc., to achieve good photoelectric performance, good thermal stability, and the effect of making stable electroluminescent devices

Inactive Publication Date: 2012-11-21
NANJING UNIV OF POSTS & TELECOMM
View PDF4 Cites 65 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, organic electroluminescent diodes have alw

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Spiro-fluorene-9,9-xanthene bipolar luminescent material, its preparation method and its application method
  • Spiro-fluorene-9,9-xanthene bipolar luminescent material, its preparation method and its application method
  • Spiro-fluorene-9,9-xanthene bipolar luminescent material, its preparation method and its application method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: spiro-9,9-xanthene fluorene

[0041] 9-Fluorenone (3.474 g, 19.3 mmol), phenol (18 g, 191.4 mmol) and methanesulfonic acid (5.0 mL, 77.2 mmol) were heated to reflux at 150°C for 24 hours under the protection of light and nitrogen. It was then cooled to room temperature, neutralized to alkaline with aqueous sodium hydroxide solution, and filtered with suction to obtain a crude product of spiro-9,9-oxanthene fluorene with high purity (yield, 85%).

Embodiment 2

[0042] Example 2: 2'-Acetyl-spiro-9,9-xanthene fluorene

[0043] Spiro-9,9-xanthene fluorene (3.3200 g, 10 mmol) and 50 mL of dichloromethane were stirred and dissolved in an ice-water bath under nitrogen protection for 20 minutes, and then acetic anhydride (0.94 mL, 10 mmol) was The constant pressure dropping funnel was slowly added dropwise to the reaction bottle, and reacted for 24 hours. The reaction mixture was slowly added to an ice-water mixture to quench, extracted with dichloromethane, the combined organic phases were dried over anhydrous magnesium sulfate, concentrated by suction filtration under pressure. Using a mixture of ethyl acetate and petroleum ether as the eluent, a white product was obtained by column chromatography (yield, 47%).

Embodiment 3

[0044] Example 3: Synthesis of 2'-isoquinolinyl-spiro-9, 9'-oxanthrene:

[0045] Under the protection of nitrogen, 2-acetyl-9,9'spiroxanthene fluorene (1.1120 g, 3 mmol) and anthranilaldehyde (1.8200 g, 15.0 mmol) were successively added to the reaction flask, and saturated potassium hydroxide was injected Solution 5mL and ethanol 25mL were refluxed overnight at 90°C, washed with water, extracted with dichloromethane, combined organic phases, dried over anhydrous magnesium sulfate, concentrated by rotary evaporator, using petroleum ether and dichloromethane as eluents, column The product was obtained by chromatography (yield, 44%). GC-MS (EI) m / z 459 [M + ];1H NMR (400 MHz, CDCl 3 ): δ (ppm) 8.13 (dd, J = 8.6, 1H), 8.0 (m, 2H), 7.84 (d, J = 7.63, 2H), 7.71 (d, J = 8.04, 1H), 7.64 (t, J = 6.98, 1H), 7.41 (m, 5H), 7.28 (s, 1H), 7.22 (m,5H), 7.08 (s, J = 2.16, 1H) , 6.80 (s, J = 8.12, 1H) , 6.44 (s, J = 7.81, 1H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

Spiro-fluorene-xanthene bipolar main materials have vertical spiral structures, so the main materials can effectively inhibit intermolecular actions, thereby the main materials can inhibit the intermolecular actions and dimer luminescence, and have good thermal stabilities and stable amorphous states. The invention relates to a spiro-fluorene-9,9-xanthene main material having a concrete designed structure shown in the specification, and concretely relates to a preparation method of the spiro-fluorene-9,9-xanthene main material, and an application of the spiro-fluorene-9,9-xanthene main material in organic light-emitting diode devices. The material has the following advantages: 1, the material has a high thermal stability and a stable amorphous state; 2, the material has a steric hindrance effect, so the material can effectively inhibit the dimer luminescence; and 3, the preparation method and the synthetic condition of the material are simple and are easy to implement, and the luminescent efficiency of the material is high. Preliminary research results of the structures of devices of the material and the properties of the material show that the material can be used in red and green light organic electroluminescent devices. Research results show that the material has a large application value and a wide application prospect in organic light-emitting diodes as the main material.

Description

technical field [0001] The present invention specifically relates to a preparation method based on functionalizing the active site of spiro-9,9-fluorenoxanthene, and relates to the steps and raw materials used in the preparation process of these materials. Background technique [0002] Due to its huge potential application value in flat panel display, organic light emitting diodes have made great progress in the past two decades. In 1987, Deng Qingyun and others used organic small molecule semiconductors to prepare low-voltage high-brightness light-emitting diodes for the first time, and then Burroughes et al. used conjugated polymers to prepare yellow-green electroluminescent devices for the first time in 1990. Especially since the first commercialization of organic light-emitting diodes in 1997, organic light-emitting diodes have been recognized as the next-generation flat-panel display and lighting technology. However, organic electroluminescent diodes have been limited ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D311/80C07D405/04C07D405/14C07D491/048C07D495/04H01L51/54
Inventor 黄维解令海赵祥华仪明东常永正游宇健石乃恩
Owner NANJING UNIV OF POSTS & TELECOMM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap