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

Asymmetric donor/receptor type organic red fluorescence small molecular material and application thereof in organic light-emitting device

A donor-acceptor-type, red fluorescence technology, applied in the field of organic electroluminescent materials, can solve the problems of low efficiency of organic red fluorescent small molecule devices, and achieve a structure-performance relationship, single structure determination, and good thermal stability. Effect

Active Publication Date: 2018-06-22
JILIN UNIV
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem of low efficiency of organic red fluorescent small molecule devices in OLEDs and to develop high-efficiency organic red fluorescent small molecule materials that do not contain precious metals, the present invention starts from the design of asymmetric donor-acceptor molecules and aims to prepare a class of high-efficiency The asymmetric donor-acceptor type organic red fluorescent small molecule material, and by optimizing the device structure, it is used in OLEDs 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
  • Asymmetric donor/receptor type organic red fluorescence small molecular material and application thereof in organic light-emitting device
  • Asymmetric donor/receptor type organic red fluorescence small molecular material and application thereof in organic light-emitting device
  • Asymmetric donor/receptor type organic red fluorescence small molecular material and application thereof in organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] P 1 The preparation comprises the following preparation steps:

[0045] m 1 Synthesis of: M 1 Prepared via the one pot method. In a 250mL round bottom flask, 9,10-phenanthrenequinone (20mmol, 4.16g), 4-bromobenzaldehyde (20mmol, 3.68g), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g) were dissolved in In 150mL of glacial acetic acid, stirred and refluxed at 120°C for 4 hours under nitrogen protection. After the reaction was completed, the reaction system was poured into 100 mL of ice water, and a large amount of precipitates appeared instantly. After suction filtration, the obtained solid was separated and purified by column chromatography (petroleum ether:dichloromethane=1:1, volume ratio) to obtain a white-brown solid (8.05 g, yield: 90%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 448.67, and the theoretical value is 448.06.

[0046]

[0047] m 2 Synthesis of: M 2 Prepared by Suzuki coupling. In a 100mL round bottom flask, M 1 (5mm...

Embodiment 2

[0054] This embodiment P 2 The preparation comprises the following preparation steps:

[0055] m 4 Synthesis of: M 4 Prepared by Suzuki coupling. In a 100mL round bottom flask, 4,7-dibromo-2,1,3-benzothiadiazole (5mmol, 1.46g), 4-cyanophenylboronic acid (5mmol, 735mg), tetrakistriphenylphosphine palladium (0.1mmol, 115mg) dissolved in 40mL of toluene and 20mL of potassium carbonate aqueous solution (2.0mol L -1 ), stirred and refluxed at 90°C for 24 hours under nitrogen protection. After the reaction, extract with dichloromethane, concentrate the extract by rotary evaporation, and separate by column chromatography (petroleum ether:dichloromethane=50:1, volume ratio) to obtain a yellow-orange solid (630 mg, yield: 40%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 315.05, and the theoretical value is 314.95.

[0056]

[0057] P 2 Synthesis of :P 2 Prepared by Suzuki coupling. In a 100mL round bottom flask, M 2 (5mmol, 2.48g), M 4 (5mmol, 1.57g), tetrakis...

Embodiment 3

[0060] This embodiment P 3 The preparation comprises the following preparation steps:

[0061] m 5 Synthesis of: M 5 Prepared by Ullmann coupling. In a 100mL round bottom flask, carbazole (10mmol, 1.67g), 1,4 dibromobenzene (10mmol, 2.34g), potassium phosphate (20mmol, 4.24g), cuprous iodide (0.2mmol, 38mg), reverse Formula-1,2-cyclohexanediamine (0.4mmol, 0.05mL) was dissolved in 40mL of toluene, stirred and refluxed at 110°C for 24 hours under nitrogen protection. After the reaction, extract with dichloromethane, concentrate the extract by rotary evaporation, and separate by column chromatography (petroleum ether:dichloromethane=8:1, volume ratio) to obtain a white solid (1.61 g, yield: 50%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 321.33, and the theoretical value is 321.02.

[0062]

[0063] m 6 Synthesis of: M 6 Prepared by Suzuki coupling. In a 100mL round bottom flask, M 5 (5mmol, 1.61g), pinacol diboronate (10mmol, 2.54g), potassium acetate (...

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 an asymmetric donor / receptor type organic red fluorescence small molecular material and application thereof in an organic light-emitting device, and belongs to the technical field of organic light-emitting materials. In the invention, high-efficiency red light emitting can be realized by using Suzuki coupling reaction and connecting the donor and receptor via a linear conjugate way; in preparation of a red light doped device, different parents are adopted and the doping concentration is optimized to realize a relatively good device effect; moreover, a molecular structure tending to be flat can emit light through triplet state-triplet state annihilation by using triplet exciton. The compound prepared in the invention has fairly high fluorescence quantum yield, and maximum external quantum efficiency of a non-doped red light device is 6.66%; at brightness 100cd m<-2> and 1,000cd m<-2>, the external quantum efficiency is 6.51% and 5.11% respectively; the efficiencyroll-off is little. The threshold voltage is low at 2.6V, and the device leads the organic red fluorescence materials in terms of comprehensive performance and is hopefully to be commercially used.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an asymmetric donor-acceptor type organic red fluorescent small molecule material and its application in preparing organic electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of low energy consumption, wide viewing angle, low cost, flexible and rollable, bright colors, etc., and are expected to become the next generation of display and lighting devices. Currently, displays based on OLEDs technology have been used in mobile phones, televisions and computers. However, current materials and device processing technologies for OLEDs are still immature. Materials are at the heart of OLEDs technology. Most of the materials that have been commercially used in display screens are metal complex phosphorescent materials centered on noble metal iridium (Ir) or platinum (Pt). However, I...

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): C07D417/10C07D417/14C09K11/06H01L51/54
CPCC09K11/06C07D417/10C07D417/14C09K2211/1029C09K2211/1014C09K2211/1007C09K2211/1044C09K2211/1051H10K85/631H10K85/657H10K85/6572
Inventor 路萍唐向阳刘辉刘福通
Owner JILIN UNIV