Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device

A technology for phosphorescent devices and compounds, which is applied in the field of organic electrophosphorescent devices, dibenzoheterocyclic spirobifluorene compounds and their preparation, and can solve the problem of poor stability of luminescence, lack of hole transport ability, brightness and luminous power Can not meet the use requirements and other problems, to achieve the effect of good stability and good electroluminescent performance

Inactive Publication Date: 2013-02-06
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the host materials used in the organic electrophosphorescent devices provided in the prior art do not have hole transport ability, and the stability of light emission is poor, and the brightness and luminous power cannot meet the requirements of use after doping with phosphorescent dyes.

Method used

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  • Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device
  • Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device
  • Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device

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Experimental program
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preparation example Construction

[0053] The present invention also provides a preparation method of the compound shown in formula I, comprising:

[0054] A preparation method of a compound shown in formula 1, comprising:

[0055] Mixing the compound shown in formula IV or formula V with the compound shown in formula VI and alkali metal carbonate in an organic solvent, and a Suzuki coupling reaction occurs under the action of a catalyst to obtain a crude product;

[0056] The crude product was refluxed and extracted, and the extract was dried and subjected to silica gel column chromatography to obtain the compound shown in formula I;

[0057]

[0058] where X is O or S, X 1 is F, Cl, Br or I.

[0059] Owing to being mixed in the organic solvent by the compound shown in IV or formula V and the compound shown in formula VI and the carbonate of alkali metal, can find out by observing the structural formula of raw material compound that actually is between benzene ring and benzene ring Coupling reaction, bec...

Embodiment 1

[0077] Preparation of 4-2-spirobifluorenyl-dibenzofuran (abbreviated as Host1)

[0078]

[0079] Add 4.00 g of 2-bromospirobifluorene and 3.20 g of 4-dibenzofuran boronic acid into a 50 ml flask, add catalyst Pd(PPh 3 ) 4 650 mg, THF 42 mL, 2M K 2 CO 3 The solution was 14 ml, refluxed at 70°C for 24 hours under the protection of argon, extracted with dichloromethane after cooling, the organic layer was dried with anhydrous sodium sulfate and then spin-dried, passed through the column with dichloromethane / petroleum ether=1:5, and spin-dried 4.25 g of the target compound was obtained with a yield of 87.3%. 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.00-8.07(m,2H),7.91(d,J=7.6Hz,2H),7.82-7.87(m,3H),7.36–7.46(m,6H),7.27–7.34(m ,2H),7.12–7.17(m,4H),6.84(d,J=7.6Hz,2H),6.79(d,J=7.6Hz,1H). 13 C NMR (100 MHz, CDCl 3 )δ (ppm): 155.9, 153.1, 149.4, 149.1, 148.7, 141.8, 141.5, 141.3, 135.9, 128.7, 127.9, 127.8, 127.7, 127.1, 126.6, 125.6, 124.7, 124.2, 124.6, 120.6, 1223.6 120.1, 120.0, ...

Embodiment 2

[0081] Preparation of 4-2-spirobifluorenyl-dibenzothiophene (abbreviated as Host2)

[0082]

[0083] Using a method similar to Example 1, 4-2-spirobifluorenyl-dibenzothiophene can be prepared using 2-bromospirobifluorene and 4-dibenzothiophene boronic acid as raw materials, with a yield of 92.2%. 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.11(t,J=4.8Hz,1H),8.03(d,J=7.6Hz,1H),7.98(d,J=8.0Hz,1H),7.90(d,J=7.6Hz ,1H),7.80-7.85(m,3H),7.75(t,J=5.2Hz,1H),7.33-7.45(m,6H),7.32(d,J=7.6Hz,1H),7.14(t, J=7.6Hz,3H),7.05(s,1H),6.85(d,J=7.6Hz,2H),6.78(d,J=7.6Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ (ppm): 149.6, 149.1, 148.5, 141.8, 141.6, 141.3, 140.1, 139.4, 138.5, 136.8, 136.1, 135.6, 128.0, 127.8, 127.7, 126.7, 126.6, 124.9, 124.1, 122.4 120.3,120.1,120.0,66.0.MS(EI):m / z 498.08(M + ).

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Abstract

The invention provides a dibenzo-heterocyclic spirobifluorene compound having a structure shown in formula I, wherein X refers to O or S, and Ar refers to substituent shown in formula II or formula III. The compound serving as a main material of an organic electrophosphorescent device is good in stability and high in luminescent intensity and current efficiency. The invention further provides a preparation method of the compound shown in the formula I and the organic electrophosphorescent device comprising the compound shown in the formula I.

Description

technical field [0001] The invention relates to the field of organic phosphorescent dyes, in particular to a dibenzoheterocyclic spirobifluorene compound, a preparation method thereof and an organic electrophosphorescent device. Background technique [0002] Since 1987, C.W.Tang et al. of Kodak reported for the first time that Alq was prepared by vacuum evaporation method. 3 Since the double-layer device structure of light-emitting materials, organic electroluminescence has received great attention. [0003] Organic electroluminescence can be divided into fluorescence and phosphorescence electroluminescence. According to the spin quantum statistics theory, the formation probability ratio of singlet excitons and triplet excitons is 1:3, that is, singlet excitons only account for 25% of the "electron-hole pairs". Therefore, the fluorescence from the radiative transition of singlet excitons only accounts for 25% of the total input energy, while the electroluminescence of phos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D333/76C09K11/06H01L51/54
Inventor 蒋佐权廖良生董首成
Owner SUZHOU UNIV
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