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Near-infrared organic fluorescent material, preparation method and application thereof

A technology of fluorescent materials and organic light-emitting layers, applied in the fields of light-emitting materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as low luminous efficiency, achieve good electroluminescence performance, improve luminous efficiency, good thermal stability and The effect of chemical stability

Inactive Publication Date: 2018-09-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, red organic fluorescent materials generally have low luminous efficiency, so how to use triplet excitons to design high-efficiency red fluorescent materials is a research hotspot in this field.

Method used

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  • Near-infrared organic fluorescent material, preparation method and application thereof
  • Near-infrared organic fluorescent material, preparation method and application thereof
  • Near-infrared organic fluorescent material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] (1) Weigh 4g of 2-cyanothiophene (32.47mmol) and dissolve it in 30mL of DMF, slowly add 3.6g of NBS into the mixture and stir for 15min, and react for 6h at room temperature in the dark after all the addition is complete. After the reaction was completed, it was extracted and purified with dichloromethane and aqueous phase, and the lower organic layer was purified by dry column chromatography. The developer was a mixed solvent of dichloromethane:petroleum ether at a volume ratio of 1:3 to obtain 4-bromo-2 - Cyanothiophene, 75% yield. 1 H NMR (500MHz, CDCl 3 )δ7.39 (d, J=4.0Hz, 1H), 7.10 (d, J=4.0Hz, 1H); MALDI-TOF MS (mass m / z): 188.9 [M + ].

[0060] (2) Weigh 1.7g of 4-bromo-2-cyanothiophene (5.7mmol) and 1.5g of iodine (5.7mmol) into a 100mL round-bottomed flask filled with 20mL of diethyl ether, and place under nitrogen protection at -78°C Next, drop 2 g of sodium methoxide 30% methanol solution (among them, the amount of sodium methoxide is 11.4 mmol) with a dro...

Embodiment 2

[0064] The device structure is ITO / HATCN(6nm) / TAPC(40nm) / BSBCN(20nm) / TPBi(40nm) / LiF(1nm) / Al. The device performance results are shown in Table 1.

[0065] Among them, HATCN is a hole injection layer, TAPC is a hole transport layer, TPBi is an electron transport layer, LiF is an electron injection layer, and the product BSBCN prepared by the present invention is an organic light-emitting layer, wherein HATCN, TAPC, TPBi and LiF are all known commodity.

Embodiment 3

[0067] The device structure is ITO / HATCN(6nm) / NPB(25nm) / TCTA(15nm) / TPBi-80%:BSBCN-20%(20nm) / TPBi(30nm) / LiF(1nm) / Al(100nm). The device performance results are shown in Table 1.

[0068] Wherein, HATCN is the hole injection layer, NPB is the hole transport layer, TCTA is the electron blocking layer, BSBCN is the doping guest material of the organic light-emitting layer, and the mass percentage is 20%, and TPBi is the doping matrix material of the organic light-emitting layer, The mass percentage is 80%, TPBi is the electron transport layer, and LiF is the electron injection layer.

[0069] Table 1: Relevant data of the device prepared in embodiment 2 and embodiment 3

[0070]

[0071] As can be seen from Table 1, the devices prepared in Example 2 and Example 3 have lower driving voltage (6.2V and 5.0V), higher current efficiency and external quantum efficiency, especially in Example 3, the device The maximum external quantum rate is 4 times that of Example 2, and the maximu...

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Abstract

The invention discloses a 2-bis(5-(4-(diphenylamino)phenyl)thiophene-2-yl)dicyanoethylene near-infrared organic fluorescent material, a preparation method and application thereof, and belongs to the technical field of organic photoelectric materials. A trans-thienyl butadiene cyanide derivative is formed by introducing a thiophene group and a triphenylamine group on the basis of a novel trans- butadiene cyanide group; due to special properties of the thiophene group, band gap level and steric configuration of a compound can be regulated, the compound has larger T1 and T2 energy level difference and smaller delta EST on high energy level, a delayed effect is reduced, the utilization rate of excitons is increased, and the luminous efficiency is remarkably increased; the compound has very good thermal stability and very good chemical stability, an organic electroluminescence device prepared as a luminous layer has the characteristics of lower driving voltage, higher current efficiency, higher external quantum efficiency and the like, and very good electroluminescent performance is obtained.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a 2-bis(5-(4-(diphenylamino)phenyl)thiophen-2-yl)dicyanoethylene near-infrared organic fluorescent material, a preparation method and its application. Background technique [0002] With the advent of the intelligent era, electroluminescent devices (OLEDs) are widely used in the field of large flat-panel full-color displays due to their advantages of high resolution, high speed, wide viewing angle, full color, lightness, flatness, portability, and low power consumption. It has a broad application prospect and becomes a master of the new generation of display technology. Among them, red organic electroluminescent devices have become a research hotspot because of their application prospects in monochrome display and white light modulation. [0003] Organic light-emitting materials are mainly divided into fluorescent materials and phosphorescent materials. A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D333/24C09K2211/1092C09K2211/1007C09K2211/1014H10K85/655H10K85/631H10K50/12H10K50/11
Inventor 路萍李金钰赵乐乐
Owner JILIN UNIV