Nonaromatic amine donor/acceptor micromolecular material as well as preparation and application

A donor-acceptor-type, aromatic amine technology, applied in the field of organic optoelectronic materials, can solve the problems of increasing difficulty in non-doped devices, low photoluminescence quantum yield, difficult application of TADF devices, etc., and achieves molecular weight determination, The effect of simplifying the OLED preparation process and high fluorescence quantum yield

Active Publication Date: 2019-05-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The only non-donor-acceptor TADF material system at present is usually derived from the n-π* transition characteristics inside the system, which makes the photoluminescence quantum yield of this type of system low, and it is difficult to realize high-efficiency TADF device applications.
So far, no high-efficiency TADF material system based on non-aromatic amine donor-acceptor systems has been reported, and it is even more difficult to realize non-doped devices with simple processes in devices

Method used

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  • Nonaromatic amine donor/acceptor micromolecular material as well as preparation and application
  • Nonaromatic amine donor/acceptor micromolecular material as well as preparation and application
  • Nonaromatic amine donor/acceptor micromolecular material as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The reaction formula of non-aromatic amines to acceptor type small molecule material 1 is as follows:

[0034]

[0035] The specific reaction steps are as follows:

[0036] Combine thianthene-1-boronic acid (3.84mmol, 1.00g), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.22mmol, 1.13g), potassium phosphate (19.20mmol, 4.07 g), Tricyclohexylphosphine (0.31mmol, 86mg), Pd 2 (dba) 3 (0.192mmol, 176mg), 100mL of 1,4-dioxane was sequentially added to the reactor, and after nitrogen was blown for 15min, the reaction was heated at 110°C for 18h. After the reaction, the system was restored to room temperature, extracted with dichloromethane and saturated brine, the organic phase was recovered, and the solvent was distilled off under reduced pressure. The crude product was separated and purified by column chromatography, and the eluent was petroleum ether / dichloromethane 5:1 to obtain the product of structure 1 with a yield of 67%. Structure 1 molecular formula: C 27 H 17 N 3 S 2 ; Molec...

Embodiment 2

[0038] The reaction formula of non-aromatic amines to acceptor type small molecule material 2 is as follows:

[0039]

[0040] The specific reaction steps are as follows:

[0041] Compared with structure 1, the difference is that thianthene-1-boronic acid is replaced with equivalent phenoxathi-4-boronic acid, and the other raw materials and steps are the same as structure 1. The structure 2 product was finally obtained with a yield of 67%. Structure 2 molecular formula: C 27 H 17 N 3 OS; molecular weight: m / z: 431.51; elemental analysis results are: C, 75.15; H, 3.97; N, 9.74; O, 3.71; S, 7.43.

Embodiment 3

[0043] The reaction formula of non-aromatic amines to acceptor type small molecule material 3 is as follows:

[0044]

[0045] The specific reaction steps are as follows:

[0046] Compared with structure 1, the difference is that thianthene-1-boronic acid is replaced with equivalent phenoxathi-1-boric acid, and other raw materials and steps are the same as structure 1. The product of structure 3 was finally obtained with a yield of 56%. Structure 3 molecular formula: C 27 H 17 N 3 OS; molecular weight: m / z: 431.51; elemental analysis results are: C, 75.15; H, 3.97; N, 9.74; O, 3.71; S, 7.43.

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Abstract

The invention belongs to the field of organic photoelectric materials, and discloses a nonaromatic amine donor / acceptor micromolecular material as well as preparation and application. The structure formula of the nonaromatic amine donor / acceptor micromolecular material is as shown in a formula (I) below, at least one of R1, R2 and R3 in the formula (I) is selected from any one donor substituent group of D1-D4, and others are phenyl groups. The nonaromatic amine donor / acceptor micromolecular material takes thioxanthone, dibenzothiophene and dibenzofuran derivative as donors while takes triazineas an acceptor, has the characteristics of simple structure and determined molecular weight, and can be easily purified and prepared in large scale. The material presents very high fluorescence quantum yield, can realize efficient non-doping OLED application, and has prominent meaning on simplifying an OLED preparation technology and lowering the cost. (The formula (I) is shown in the description).

Description

Technical field [0001] The invention belongs to the field of organic photoelectric materials, and specifically relates to a non-aromatic amine donor-acceptor type small molecule material and its preparation and application. Background technique [0002] Organic light-emitting diode (OLED) devices show great application prospects in the field of flat panel displays and solid-state light sources with their unique high-quality display, high color resolution, wide viewing angle, healthy light source characteristics near the solar spectrum, and ultra-fast response. In the current rapid development of the OLED field, further improve the efficiency of organic optoelectronic devices, develop a new type of organic small molecule material system with stable structure, convenient purification and simple preparation process, so as to achieve higher device efficiency and simpler device preparation process Vital. At present, compared with polymer materials, the research and development of sma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D405/14C07D409/04C07D409/14C07D411/04C07D411/14H01L51/54
Inventor 苏仕健蔡欣佚乔振洋
Owner SOUTH CHINA UNIV OF TECH
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