Unlock instant, AI-driven research and patent intelligence for your innovation.

Thermally activated delayed fluorescent material based on carbazole and diphenyl sulfone and preparation method thereof

A thermal activation delay and fluorescent material technology, applied in the direction of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of high production cost, unsuitable for wet film formation, poor solubility, etc., and achieve the preparation method Simple and feasible, easy to prepare on a large scale, and the effect of high triplet energy level

Inactive Publication Date: 2017-07-25
SOUTHEAST UNIV CHENGXIAN COLLEGE
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since these phosphorescent guest materials (generally Ir-type complexes) contain noble metals, these noble metals are non-renewable resources, the production cost is high, and environmental problems are likely to occur during the production process.
Due to the poor solubility of these complexes in organic solvents, they will be unstable after a long time, so they are not suitable for wet film formation
These problems have restricted the large-scale application of organic electrophosphorescent devices.

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
  • Thermally activated delayed fluorescent material based on carbazole and diphenyl sulfone and preparation method thereof
  • Thermally activated delayed fluorescent material based on carbazole and diphenyl sulfone and preparation method thereof
  • Thermally activated delayed fluorescent material based on carbazole and diphenyl sulfone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of 9-{3,5-bis[(4-phenylsulfone)phenyl]}-9H-carbazole

[0035] In a 500mL three-necked flask, add 6.06g (17.6mmol) of diphenylsulfone-4-boronic acid pinacol ester, 3.21g (8mmol) of 9-(3,5-dibromophenyl)-9H-carbazole, (Triphenylphosphine)palladium 1.0g, 20mL potassium carbonate aqueous solution (4.3g potassium carbonate dissolved in 20mL water), 40mL ethanol and 200mL toluene were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 24h. The reaction solution was cooled to room temperature, then extracted with dichloromethane (2*200 mL), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:10~1:3 was eluted to obtain a white solid. 1 H NMR (300MHz, CDCl 3 ):δ(ppm)8.25-8.13(d,2H),8.10-7.92(m,7H),7.59-7.52(m,6H),7.46-7.44(m,6H),7.37-7.31(m,6H) ,7.29(s,2H).

Embodiment 2

[0036] Example 2: Preparation of 9-{3,5-bis[(4-phenylsulfone)phenyl]}-9H-tricarbazole

[0037] In a 500mL three-necked flask, add 6.06g (17.6mmol) of diphenylsulfone-4-boronic acid pinacol ester, 5.85g (8mmol) of 9-(3,5-dibromophenyl)-9H-tricarbazole, Tetrakis(triphenylphosphine)palladium 1.0g, 20mL potassium carbonate aqueous solution (4.3g potassium carbonate dissolved in 20mL water), 40mL ethanol and 200mL toluene were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 24h. The reaction solution was cooled to room temperature, then extracted with dichloromethane (2*200 mL), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:10~1:3 was eluted to obtain a white solid. 1 H NMR (300MHz, CDCl 3 ): δ(ppm)8.16-8.04(d,4H),8.00-7.94(d,4H),7.75-7.55(m,11H),7.43-7.40(m,16H),7.34-7.31(m,2H) ,7.11-7.03(m,6H).

Embodiment 3

[0038] Example 3: Preparation of 9-{3,5-bis[(3-phenylsulfone)phenyl]}-9H-carbazole

[0039] In a 500mL three-necked flask, add 6.06g (17.6mmol) of diphenylsulfone-3-boronic acid pinacol ester, 3.21g (8mmol) of 9-(3,5-dibromophenyl)-9H-carbazole, (Triphenylphosphine)palladium 1.0g, 20ml potassium carbonate aqueous solution (4.3g potassium carbonate dissolved in 20mL water), 40ml ethanol and 200mL toluene were mixed uniformly, and reflux reaction was carried out under nitrogen protection for 24h. The reaction solution was cooled to room temperature, then extracted with dichloromethane (2*200 mL), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:20~1:10 was eluted to obtain a white solid. 1 H NMR (300MHz, CDCl 3 ): δ (ppm) 8.26 (s, 2H), 8.11-7.96 (m, 8H), 7.85-7.76 (m, 3H), 7.53-7.40 (m, 12H), 7.34-7.31 (m, 4H).

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

The invention discloses a heat-activated delayed fluorescence material which is formed by connecting carbazolyl or tricarbazolyl group (R1) with hole transmission capacity and 2- position, 3- position or 4- position of diphenyl sulfuryl group with electronic transmission capacity through a benzene ring, wherein R1 is carbazolyl or tricarbazolyl group, and is substituted for 1- position of the benzene ring; and R2 is (2-phenylsulfuryl)phenyl, (3-phenylsulfuryl)phenyl or (4-phenylsulfuryl)phenyl, and is substituted for 3,5- position on the phenyl ring. The heat-activated delayed fluorescence material has the advantage of short synthesis route; and the synthesis method is simple and easy to implement, and is suitable for wide application. The singlet state-triplet state energy level difference of the material is less than 0.3 eV; and the material can emit blue light, and can be used as a heat-activated delayed fluorescence material.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and in particular relates to a thermally activated delayed fluorescent material based on carbazole and diphenyl sulfone, a preparation method and properties thereof. Background technique [0002] In electrophosphorescent devices, the light-emitting layer almost always adopts the structure of the host-guest light-emitting system, that is, the host-guest light-emitting material is doped with the guest light-emitting material, and the host light-emitting material with higher energy transfers energy to the guest to emit light. Therefore, The emission color of the device can be tuned by selecting different guest materials. However, since these phosphorescent guest materials (generally Ir-type complexes) contain noble metals, these noble metals are non-renewable resources, the production cost is high, and environmental problems are likely to occur during the production process. Due to the poor sol...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D209/88H01L51/54
Inventor 黄斌蒋伟刘月松夏翰尹智慧钱巍
Owner SOUTHEAST UNIV CHENGXIAN COLLEGE