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Fluorene-based bridged blue phosphorescent host material and its preparation method and application

A technology of triphenylamine fluorene and diphenylphosphine, which is used in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of hindering wide application, low glass transition temperature, and low material stability. , to achieve the effect of good hole and electron transport ability, high triplet energy, and increasing effective molecular weight

Active Publication Date: 2011-12-14
武汉承胜创业投资有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature of m-CP is low, and the stability of the material itself is not high, which hinders its wide application.

Method used

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  • Fluorene-based bridged blue phosphorescent host material and its preparation method and application
  • Fluorene-based bridged blue phosphorescent host material and its preparation method and application
  • Fluorene-based bridged blue phosphorescent host material and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: when R in formula I 1 and R 2 is carbazolyl, R 3 and R 4 When it is phenyl, it is named as 9,9-diphenyl-3,6-dicarbazolylfluorene (BBDC), when R in formula I 1 and R 2 is carbazolyl, R 3 , R 4 When they are phenyl and 3-(9-phenylcarbazol) groups, they are named 9-phenyl-9-carbazolyl-3,6-dicarbazolylfluorene (BCDC), and their structural formulas are as follows:

[0043]

[0044] BBDCBCDC

[0045] The BBDC of the present invention can be synthesized by the following method.

[0046] Step 1: dissolving phenanthrenequinone and liquid bromine in nitrobenzene, heating to 80°C for 16 hours to obtain dibromophenanthrenequinone;

[0047] Step 2: dissolving dibromophenanthrenequinone, potassium hydroxide, and potassium permanganate in water, and reacting for 6 hours under reflux conditions to obtain dibromofluorenone;

[0048] Step 3: Dibromofluorenone and Benzene Grignard reagent were reacted in tetrahydrofuran at room temperature for 5 hours to obtain 9...

Embodiment 2

[0057] Embodiment 2: when R in formula I 1 and R 2 For diphenylphosphoryloxy, R 3 and R 4 When it is phenyl, it is named as 9,9-diphenyl-3,6-bis(diphenylphosphoryloxy)fluorene (BBDP); when R in formula I 1 and R 2 For diphenylphosphoryloxy, R 3 , R 4 When they are phenyl and 3-(9-phenylcarbazol) group respectively, they are named as 9-phenyl-9-carbazolyl-3,6-bis(diphenylphosphoryloxy)fluorene (BCDP), which The structural formula is as follows:

[0058]

[0059] BBDPBCDP

[0060] The BBDP of the present invention can be synthesized by the following method.

[0061] Step 1: dissolving phenanthrenequinone and liquid bromine in nitrobenzene, heating to 80°C for 16 hours to obtain dibromophenanthrenequinone;

[0062] Step 2: dissolving dibromophenanthrenequinone, potassium hydroxide, and potassium permanganate in water, and reacting for 6 hours under reflux conditions to obtain dibromofluorenone;

[0063] Step 3: Dibromofluorenone and Benzene Grignard reagent were reac...

Embodiment 3

[0072] Embodiment 3: when R in formula I 1 , R 2 For the second generation of tert-butyl substituted carbazolyl, R 3 , R 4 When they are phenyl and 3-(9-phenylcarbazolyl) respectively, they are named 9-phenyl-9-carbazolyl-3,6-di(di-tert-butylcarbazolyl)fluorene (BCDTC) , its structural formula is as follows:

[0073]

[0074] BCDTC

[0075] The above-mentioned BCDTC can be synthesized by the following method:

[0076] Step 1: dissolving phenanthrenequinone and liquid bromine in nitrobenzene, heating to 80°C for 16 hours to obtain dibromophenanthrenequinone;

[0077] Step 2: dissolving dibromophenanthrenequinone, potassium hydroxide, and potassium permanganate in water, and reacting for 6 hours under reflux conditions to obtain dibromofluorenone;

[0078] Step 3: Dibromofluorenone and Benzene Grignard reagent were reacted in tetrahydrofuran at room temperature for 5 hours to obtain 9-benzene-substituted dibromofluorene;

[0079] Step 4: Add an appropriate amount of tr...

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Abstract

The invention relates to an organic blue phosphorescent main body material with fluorene as a center unit structure, and a preparation method and application thereof in a blue organic light-emitting diode (OLED). In the material, fluorene is used as a main body structure, and different electron properties of groups are bonded to 3-, 6- and 9- positions of fluorene, thereby the conjugated system of the main body material is effectively reduced, the effective molecular weight of the compound is increased, and the triplet energy and glass transition temperature of the material are improved to some extent. In addition, the polarity of the compound can be adjusted by drawing / withdrawing electron groups; compared with the commonly used blue phosphorescent main body materials including 4,4'-(9-carbazole)-biphenyl (CBP) and N,N'-dicarbazoyl-1,3-benzene (m-CP), the efficiency roll-off problem under a high luminescence condition of the blue phosphorescent OLED devices is effectively solved under a condition of appropriate polarization rate; and the main body material can be widely used in the organic light-emitting field.

Description

technical field [0001] The invention belongs to the field of photoelectric material application science and technology, and specifically relates to the preparation of high triplet energy blue phosphorescence host material with fluorene as the basic structural unit and modified at the 3, 6, and 9 positions of fluorene and its application in organic electroluminescent devices. (OLED) applications technical background [0002] The phenomenon of organic electroluminescence was first discovered in 1963, when organic anthracene crystals were used as light-emitting materials. Because the driving voltage of this device is as high as 400V, and the device efficiency and life are far inferior to inorganic electroluminescent devices, it did not attract people's attention at that time. In 1987, Deng Qingyun's (Tang, C.W.et al.Appl.Phys.Lett.1987, 52, 913) research group first proposed the OLED structure of an organic multilayer amorphous film; in 1990, Burroughes et al. (Burroughes, J.H...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07F9/53C07F9/572C07D403/14C07D519/00C07D471/14C09K11/06H01L51/54
Inventor 王磊刘雅坤黄宏杨晓陈长清
Owner 武汉承胜创业投资有限公司
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