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Blue luminescent materials based on bifluorene derivative

A technology of blue light-emitting materials and fluorene derivatives, applied in the directions of light-emitting materials, compounds of Group 5/15 elements of the periodic table, chemical instruments and methods, etc., to improve thermal stability, reduce interactions, and reduce emission. Effect

Pending Publication Date: 2022-01-07
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, red and green light devices can meet people’s requirements in terms of luminous stability, luminous efficiency, and device life. Only blue light devices need to be further improved in terms of balance of luminous color purity, luminous efficiency, and lifespan.

Method used

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  • Blue luminescent materials based on bifluorene derivative
  • Blue luminescent materials based on bifluorene derivative
  • Blue luminescent materials based on bifluorene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: The synthesis route of the electron donor bisfluorene DF is as follows

[0028]

[0029] The specific synthesis process is as follows:

[0030] Take a two-necked flask, add 4.27g of p-bromophenol, 6.63g of anhydrous potassium carbonate, 33mL of N,N-dimethylformamide (DMF), 3.3g of bromobutane, and react at 80°C for 10 hours to obtain 1-bromo - 4-butoxybenzene 3.6 g (66% yield).

[0031] Take a two-necked flask, prepare 3.62 g of 1-bromo-4-butoxybenzene into Grignard reagent, add 3.1 g of 2-bromofluorenone, 60 mL of tetrahydrofuran, and reflux at 65°C for 20 hours to obtain 2-bromo-9-(4 -butoxyphenyl)-9-fluorenol 4.4 g (55% yield).

[0032] Take a two-neck flask, add 1.8g of 2-bromofluorenone, 6.6g of phenol, and 10mL of methanesulfonic acid, and react at 50°C for about 20h to obtain 1.87g of a white powdery product.

[0033] Take a two-necked flask, add 1.7g of the white powder obtained in the previous step, 0.62g of anhydrous potassium carbonate, 30mL ...

Embodiment 2

[0038] Embodiment 2: compound (DF) 2 SO 2 and (DF) 2 The synthetic route of PO is as follows

[0039]

[0040] (DF) 2 SO 2 Preparation: Take the reaction test tube, add DF 1.5g (1.94mmol), 4,4-dibromodiphenyl sulfone 0.2g, potassium tert-butoxide 0.175g, tert-butyldiphenylphosphine 0.04g, tri-(diphenyl Benzylacetone) dipalladium 0.1g, toluene 4mL, react at 110°C for 30h to obtain the product (DF) 2 SO 2 0.27g.

[0041] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.77(dd,J=13.2,7.3Hz,12H),7.57(d,J=9.9Hz,4H),7.53–7.47(m,4H),7.38(q,J=8.0Hz,10H ),7.34–7.28(m,4H),7.27(d,J=5.6Hz,1H),7.25–7.23(m,1H),7.18–7.13(m,8H),7.07(d,J=8.7Hz, 4H),6.77(t,J=7.0Hz,12H),3.90(t,J=5.9Hz,12H),1.78–1.68(m,12H),1.50–1.42(m,12H),0.95(td,J =7.3, 2.6Hz, 18H). 13 CNMR (101MHz, CDCl 3 ,ppm)δ158.23,157.94,152.62,152.33,152.26,141.28,140.39,139.70,139.47,139.40,139.10,137.75,129.15,129.10,128.95,127.93,127.75,127.34,126.53,126.06,124.61,124.51,114.39,114.10 ,67.58,64.84,64.29,31.36,19.25,13.84. MALDI-TOF, ...

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Abstract

The invention discloses blue luminescent materials based on a bifluorene derivative, different electron withdrawing groups are introduced into a ninth reaction site of bifluorene through a C-H coupling reaction in presence of tri (dibenzylideneacetone) dipalladium (0) to obtain a series of blue luminescent materials with distorted structures; reaction raw materials are wide in source and are common organic small molecular materials, the synthesis cost is low, and industrialization is facilitated; the luminescent material has the advantages of wide energy gap, stable luminescence wavelength, good thermal stability, high fluorescence quantum yield, good solubility in general organic solvents, and suitableness for preparing corresponding electroluminescent devices through a solution processing mode. The material still maintains excellent blue light emission in a solid film state, and can improve the luminous efficiency of an organic electroluminescent device, maintain blue light emission and improve the color purity and saturation of blue light emission of the device when being applied to the organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a class of blue luminescent materials based on bisfluorene derivatives. Background technique [0002] From black and white screens to color screens, from curved screens to folding screens, the rapid development of personal communication devices and the upgrading of smartphones in recent years have brought Organic Light Emission Diodes (OLEDs) technology from behind the scenes to the front. With the popularization of various smart electronic devices, OLED display technology is gradually integrating into our daily life. [0003] Compared with other mainstream display technologies, OLED display has better performance in terms of device response, power consumption and display contrast due to its self-luminous characteristics. In addition, in the field of flexible display and transparent display technology, OLED has also shown better application potential...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C317/22C07C49/84C07F9/53
CPCC09K11/06C07C317/22C07C49/84C07F9/5325C09K2211/1007C09K2211/1011C09K2211/1014C07C2603/18
Inventor 袁鑫磊姜鸿基
Owner NANJING UNIV OF POSTS & TELECOMM
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