Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes

A light-emitting diode, anthraquinone group technology, applied in the field of organic electroluminescent devices, can solve the problems of unbalanced injection and transport of holes and electrons, low electron affinity, difficult electron injection, etc., and achieves high yield, The effect of good performance and great commercialization potential

Active Publication Date: 2016-04-13
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the electron affinity of this type of compound is low, electrons are not easily injected into it, and the injection and transport of holes and electrons are unbalanced.

Method used

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  • Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes
  • Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes
  • Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Example 12-(12,12',15,15'-tetra-n-butyl-6,6'-diisooctyl-12,15-dihydro-6H-cyclopentadiene[1,2-b: The preparation of 5,4-b'] bisfluorenyl) anthracene-9,10-dione (LTTPHAA) is as follows:

[0039]

[0040] Step 1 Preparation of intermediate 1-1: Dissolve 1.15g (1.45mmol) LTTPH in 45-75mL of chloroform, add 0.23g (1.45mmol) of liquid bromine dropwise, keep at -10-10°C, and react overnight; After extraction with methyl chloride, drying, and rotary evaporation to remove the solvent, 1 g of white solid was obtained by recrystallization from dichloromethane and ethanol, with a yield of 80%.

[0041] serial number LTTPH (g) Liquid bromine (g) Chloroform (mL) temperature(℃) product (g) 1 1.15 0.23 45 -10 0.93 2 1.15 0.23 55 0 1 3 1.15 0.23 75 10 0.96

[0042]Step 2 Preparation of LTTPHAA: 8222 Add 0.36g (0.41mmol) of intermediate 1-1 and 0.14g (0.41mmol) of 2-anthraquinone boric acid pinacol ester into a three-necked flask, va...

Embodiment 22

[0047] Example 22,2'-(12,12',15,15'-tetra-n-butyl-6,6'-diisooctyl-12,15-dihydro-6H-cyclopentadiene[1,2 -b: Preparation of 5,4-b']bifluorenyl)bis(anthracene-9,10-dione) (DAALTTPH), its synthetic route is as follows:

[0048]

[0049] Step 1 Preparation of intermediate 2-1: Dissolve 0.92g (1.16mmol) LTTPH in 45-75mL of chloroform, add 0.37g (2.32mmol) of liquid bromine dropwise, keep at -10-10°C, and react overnight; After extraction with methyl chloride, drying, and rotary evaporation to remove the solvent, 0.93 g of white solid was obtained by recrystallization from dichloromethane and ethanol, with a yield of 85%.

[0050] serial number LTTPH (g) Liquid bromine (g) Chloroform (mL) temperature(℃) product (g) 1 0.92 0.37 45 -10 0.90 2 0.92 0.37 55 0 0.93 3 0.92 0.37 75 10 0.88

[0051] Step 2 Preparation of DAALTTPH: Add 0.95g (1mmol) of intermediate 2-1 and 0.67g (2mmol) of 2-anthraquinone borate pinacol ester into a three...

Embodiment 32-

[0056] Example 32-[12,12',15,15'-tetra-n-butyl-10-(9-9H-carbazolyl)-6,6'-diisooctyl-12,15-dihydro-6H - Preparation of cyclopentadiene[1,2-b:5,4-b']difluorenyl]anthracene-9,10-dione (CzLTTPHAA), whose synthetic route is as follows:

[0057]

[0058] Step 1 Preparation of intermediate 3-1: 1.14g (1.2mmol) of intermediate 2-1 prepared in Example 2 and 0.4g (1.2mmol) 2-anthraquinoneboronic acid pinacol ester were added to a three-necked flask, Vacuumize and fill with nitrogen for 3 times, add 50mg tetrakis(triphenylphosphine)palladium; mix 5~20mL toluene / tetrahydrofuran mixed solvent (1:1) and 2~4mL potassium carbonate / potassium fluoride after deoxygenation by nitrogen bubbling Solvent (2mol / L) was added into the reaction flask respectively, heated to 80-100°C, and stirred for 24-72 hours. After the reaction was completed, it was extracted with dichloromethane, dried, and the solvent was removed by rotary evaporation, and purified by silica gel column chromatography to obtain ...

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Abstract

The invention relates to a novel fluorene bipolar fluorescent material based on an anthraquinone group and application of the novel fluorene bipolar fluorescent material in organic light emitting diodes; the material has a D-Pi-A type or an A-Pi-A type intramolecular charge transfer structure, the general structural formula is shown in the formula I; the material shown in the formula I has bipolar charge carrier transport property, the organic light emitting diodes prepared by utilizing the material have good luminescence property, the synthesis and purification operation of the material are simple, the yield is high, and the material is an ideal choice for a material for changing yellow light to red light in the organic light emitting diodes; it can be expected that the material can be an organic electroluminescent material with the commercial potential.

Description

technical field [0001] The invention relates to a preparation method of a novel fluorene bipolar fluorescent material based on anthraquinone groups and its application in organic light-emitting diodes, belonging to the field of organic electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have received extensive attention in the field of flat-panel displays due to their advantages such as low driving voltage, fast response speed, low power consumption, high contrast ratio, and wide viewing angle; Display, thus becoming the development direction of a new generation of solid-state lighting sources, is currently one of the most attractive technologies in the field of optoelectronic devices and flat panel displays. However, in the process of realizing the industrialization of OLED, there are still problems such as low yield, unsatisfactory luminous efficiency and poor stability. [0003] Organic electroluminescent materials are one of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C50/16C07D209/86H01L51/54
CPCC09K11/06C07C50/16C07D209/86C09K2211/1029C09K2211/1011H10K85/626H10K85/6572H10K50/00
Inventor 钱妍陈昊杨涛黄维解令海张新稳
Owner NANJING UNIV OF POSTS & TELECOMM
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