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Red organic fluorescence material containing benzothiadiazole derivative as well as preparation method and application of red organic fluorescence material

A technology of benzothiadiazoles and fluorescent materials, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of increased molecular dipole interaction, high radiation transition rate, etc.

Inactive Publication Date: 2018-11-20
JILIN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, due to the space-separated transition orbitals of the donor-acceptor molecules, it is not easy to form a high radiative transition rate, and too strong donor-acceptor interaction will lead to an increase in the dipole interaction of the molecule, and aggregation in the solid state will bring a radiative transition rate. come quite adverse

Method used

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  • Red organic fluorescence material containing benzothiadiazole derivative as well as preparation method and application of red organic fluorescence material
  • Red organic fluorescence material containing benzothiadiazole derivative as well as preparation method and application of red organic fluorescence material
  • Red organic fluorescence material containing benzothiadiazole derivative as well as preparation method and application of red organic fluorescence material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: compound sample preparation

[0068] (1) Weigh 20g (100mmol) 10H-phenothiazine, 31.9g (150mmol) 4-p-bromo-tert-butylbenzene, 14.4g (150mmol) sodium tert-butoxide, 2.9g (10mmol) tri-tert-butyl tetrafluoroborate The base phosphine was added to a 250mL round bottom flask, dissolved in 60mL toluene solvent, and after being vacuumed and nitrogen gas introduced, a catalyst 27.5mg Pd was added to the reaction system. 2 (dba) 3 (3mmol), the reaction was placed in an oil bath at 110°C for 48h. After completion of the reaction, extract with dichloromethane and aqueous phase, take the lower organic layer and carry out dry column chromatography purification, developing agent is sherwood oil, obtain light yellow crystalline powder 40g, i.e. 10-(4-(tert-butyl)benzene Base) phenothiazine, the reaction yield is 90%. 1 H NMR (500MHz, CD 2 Cl 2 )δ7.66(s,1H),7.33(d,J=7.5Hz,1H),7.15–6.77(m,3H),6.24(s,1H),1.54(d,J=20.4Hz,1H), 1.40–1.26(m,1H); MALDI-TOF MS(mass m / z):331.4...

Embodiment 2

[0074] The device structure is ITO / HATCN(6nm) / NPB(25nm) / TCTA(15nm) / TBPPTZ(20nm) / TPBi(30nm) / LiF(1nm) / Al(100nm), and the device performance results are shown in Table 1.

[0075] Among them, HATCN is the hole injection layer, NPB is the hole transport layer, TBPPTZ is the light-emitting layer prepared by the present invention, TCTA is the electron blocking layer, TPBi is the electron transport layer, and LiF is the electron injection layer.

Embodiment 3

[0077] The device structure is ITO / HATCN(6nm) / NPB(25nm) / TCTA(15nm) / TPBi:TBPPTZ-20%(20nm) / TPBi(30nm) / LiF(1nm) / Al(100nm). The device performance results are shown in Table 1.

[0078] Wherein, HATCN is the hole injection layer, NPB is the hole transport layer, TCTA is the electron blocking layer, TBPPTZ is the guest of the light-emitting layer, and the doping mass percentage is 20%, and TPBi is the matrix of the light-emitting layer, and the doping mass percentage is 80%, TPBi is the electron transport layer, and LiF is the electron injection layer.

[0079] Table 1: Device related parameters

[0080]

[0081] It can be seen from Table 1 that Embodiment 2 and Embodiment 3 have lower driving voltage, higher current efficiency and external quantum efficiency, and have shown good effects on blue light material devices. Using TPBi as the doping matrix material can effectively improve the external quantum efficiency and brightness of the device. The emission peak of the doped de...

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Abstract

The invention discloses a red organic fluorescence material containing a benzothiadiazole derivative, namely 4,7-bis(10-(4-(tert-butyl) phenyl)-10H-phenothiazine-3-yl) diazosulfide as well as a preparation method and application of the red organic fluorescence material, and belongs to the technical field of organic optoelectronic materials. The red organic fluorescence material is characterized inthat 10-(4-(tert-butyl) phenyl) phenothiazine is used as a donor, and 10-(4-(tert-butyl) phenyl) phenothiazine with a D-A-D structure is obtained by a phenothiazine 3rd-bit bridging mode of benzothiadiazole; due to peculiar properties of a tert-butyl phenyl group, the dissolving processing performance and electronic transmission performance of a derivative compound donor material are improved, carrier support is more balanced in transportation and the luminous efficiency is improved; the prepared compound has high thermal stability and chemical stability and proper energy level, and can be applied to the field of organic electroluminescence as a red light material; and a prepared organic electroluminescence device has the characteristics of lower drive voltage, higher current efficiency,external quantum efficiency and the like and obtains higher electroluminescence.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials, in particular to a benzothiadiazole derivative—4,7-bis(10-(4-(tert-butyl)phenyl)-10H-phenothiazin-3-yl ) Benzothiadiazole red organic fluorescent material, preparation method and application thereof. Background technique [0002] In recent years, LED, which once represented the advanced technology in the field of optoelectronics, has gradually withdrawn from the stage of history. Organic electroluminescent devices (OLEDs), with their high resolution, high speed, wide viewing angle, full color, Power consumption and other advantages, become a master of the new generation of display technology. At present, mobile phones, TVs, tablet computers and digital cameras with OLED display screens have appeared on the market and have broad prospects for development. Nevertheless, organic electroluminescent devices still have problems such as high process cost and lack of high-perfo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06H01L51/54
CPCC09K11/06C07D417/14C09K2211/1051H10K85/657
Inventor 路萍李金钰赵乐乐
Owner JILIN UNIV
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