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Biphenyl-based host materials for bipolar carrier transport and their applications

A technology of host material and electron transport performance, applied in the direction of luminescent materials, electric solid devices, semiconductor devices, etc., can solve the problems of poor carrier transport performance, low yield, low device efficiency, etc., and achieve high-efficiency electroluminescence performance effect

Active Publication Date: 2015-08-19
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In recent years, green and red phosphorescent electroluminescent devices have achieved practically high efficiencies; however, the development of sky blue and deep blue photophosphorescent relatively lag
Among them, one of the important reasons is the lack of host materials with both high triplet energy level and bipolar carrier transport performance.
In 2004, Forrest and Thompson et al. (X. Ren, J. Li, R. J. Holmes, P. I. Djurovich, S. R. Forrest, M. E. Thompson, Chem. Mater. 2004, 16, 4743) reported that a compound based on tetraphenyl silicon with high triplet energy level was used as the host material of deep blue FIr6, but the efficiency of the device was very low due to poor carrier transport performance, and the best external quantum efficiency was only 9.1%
However, bipolar host materials modified at the 2,2' position of biphenyl have not been reported yet.

Method used

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  • Biphenyl-based host materials for bipolar carrier transport and their applications
  • Biphenyl-based host materials for bipolar carrier transport and their applications
  • Biphenyl-based host materials for bipolar carrier transport and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 2-(9-carbazolyl)-2’-(diphenylphosphinyl)biphenyl (abbreviated as Host1, structural formula as follows)

[0027]

[0028] Add 1.3 g of 2-bromo-2'-(diphenylphosphinyl)biphenyl, 1 g of carbazole, 828 mg of potassium carbonate, 192 mg of 18-crown-6 ether and 8 mL of o-dichlorobenzene into a 50 mL flask reflux at 160 degrees Celsius for 18 hours under the protection of argon, pour it into saturated ammonium chloride aqueous solution after cooling, extract with dichloromethane, wash with brine, dry with anhydrous sodium sulfate, filter, and spin dry, and the crude product is washed with chloroform / ethyl acetate Ester = 10:1 (v / v) column chromatography, spin-dried to obtain the product. Yield 83%. 1 H NMR (CDCl 3 , 300 MHz): 8.26-8.23 (d, J = 8.1 Hz, 1H), 8.09-8.06 (d, J = 7.8 Hz, 1H), 7.95-7.93 (d, J = 7.2 Hz, 1H), 7.78-7.71 (m, 2H), 7.65-7.40 (m, 11H), 7.30-7.21 (m, 4H), 7.14-7.09 (t, J = 7.5 Hz, 1H), 7.05-6.86 (m, 5H); 13 C NMR (CDCl 3, 300 MHz...

Embodiment 2

[0030] Preparation of 2-(3,6-di-tert-butyl-9-carbazolyl)-2’-(diphenylphosphinyl)biphenyl (abbreviated as Host2, structural formula as follows)

[0031]

[0032] Mix 1.3 g of 2-bromo-2'-(diphenylphosphinyl)biphenyl, 1 g of 3,6-(di-tert-butyl)carbazole, 828 mg of potassium carbonate, 192 mg of 18-crown-6 ether and Add 8 milliliters of o-dichlorobenzene into a 50 milliliter flask, reflux at 160 degrees Celsius for 18 hours under argon protection, pour into saturated aqueous ammonium chloride solution after cooling, extract with dichloromethane, wash with brine, dry over anhydrous sodium sulfate, filter, Spin-dried, the crude product was subjected to column chromatography with chloroform / ethyl acetate=10:1 (v / v), and spin-dried to obtain the product. The yield is 80%. 1 H NMR (CDCl 3 , 300 MHz): 8.15-8.13 (d, J = 8.4 Hz, 1H), 8.07 (s, 1H), 7.93 (s, 1H), 7.80-7.74 (m, 2H), 7.56-7.34 (m, 11H), 7.27-7.19 (m, 3H), 7.03- 6.95 (m, 5H), 1.47 (s, 9H), 1.39 (s, 9H); 13 C NMR (CDCl...

Embodiment 3

[0033] Embodiment 3 Preparation of electrophosphorescent device

[0034] Such as image 3 As shown, the electrophosphorescent device in which the bipolar carrier transport material of the present invention is used as the main body of the light-emitting layer includes glass and conductive glass (ITO) substrate layer 1, hole injection layer 2 (molybdenum trioxide MoO 3 ), hole transport layer 3 (4,4’-two ( N -Phenyl- N -naphthyl)-biphenyl NPB), electron blocking layer 4 (4,4',4''-tris(N-carbazole)triphenylamine TCTA), light-emitting layer 5 (the host material prepared in Examples 1~2 doped heterophosphorescent iridium complex), hole-blocking layer 6 (1,3,5-tris(m-pyridyl-3-)phenylbenzene Tm), electron-transporting layer 7 (1,3,5-tris(N- phenylbenzimidazole-2-)phenyl TPBi), cathode layer 8 (LiF / Al).

[0035] The electroluminescent device is made by methods known in the art, such as by reference ( Adv. Mater. 2004, 16 , 537.) made by the disclosed method. The specific...

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Abstract

The invention discloses a material with high triplet level and bipolar current carrier transmission performance, which contains a carbazole unit DN with hole transmission performance and a diphenylphosphine oxide unit An with electron transmission performance, which are connected at 2,2'- site of biphenyl. The structure of the material is disclosed as the following formula. The synthesis method of the main material is simple and easy to implement, and suitable for wide application. The electroluminescent phosphor device made of the main material has the advantages of high efficiency, high brightness and low-efficiency attenuating electroluminescent performance, and can be widely used in the field of organic electroluminescence.

Description

technical field [0001] The invention relates to a phosphorescent bipolar carrier transporting host material and its application in the field of electroluminescence, belonging to the field of luminescent materials. Background technique [0002] Since 1987, C. W. Tang et al. of Kodak Company 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. Organic electroluminescence can be divided into fluorescence and phosphorescence electroluminescence, and electroluminescence of phosphorescent materials can utilize the energy of all excitons, which has greater advantages. [0003] Most of the current phosphorescent electroluminescent devices adopt the host-guest structure, that is, the phosphorescent emitting substance is doped in the host substance at a certain concentration, so as to avoid concentration quenching and triplet-trip...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/572C09K11/06H01L51/54
Inventor 杨楚罗樊聪秦金贵
Owner WUHAN UNIV