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Tetraphenyl carbon-based OLED main body material and application thereof in preparation of OLED device

A host material, tetraphenyl carbon technology, which is applied in the fields of electric solid devices, semiconductor devices, organic semiconductor devices, etc., can solve the problems of wide energy band gap and OLED host materials cannot be provided at the same time, so as to improve efficiency and balance Hole and electron transport capability, low cost effect

Inactive Publication Date: 2018-11-06
YANGTZE NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a tetraphenyl carbon-based OLED host material, which solves the problem that the existing OLED host material cannot simultaneously have a wide energy band gap, adjustable HOMO and LUMO energy. level and the issue of matching hole and electron transport capabilities

Method used

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  • Tetraphenyl carbon-based OLED main body material and application thereof in preparation of OLED device
  • Tetraphenyl carbon-based OLED main body material and application thereof in preparation of OLED device
  • Tetraphenyl carbon-based OLED main body material and application thereof in preparation of OLED device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The structural formula is Synthesis of the first target compound:

[0024] Add n-butyllithium n-hexane solution (6.6mL, 10.5mmol) dropwise to a solution containing 1,4-dibromobenzene (2.36g, 10mmol) in THF (20mL), at -78°C under the protection of inert gas argon Reaction 1h. Then, carbon tetrachloride (1.05 mL, 5 mmol) was added into the reaction solution and the above conditions were maintained for 2 h, then slowly heated to room temperature 27° C. and stirred for 12 h. Finally, 30 mL of water was added to interrupt the reaction and extraction was performed with chloroform. The obtained organic layer was purified by column chromatography to obtain the intermediate product TBrBen (2.15g, yield 68.5%). The intermediate product is identified and analyzed by a mass spectrometer, and the result is: mass spectrum (EI): m / z C 25 h 16 Br 4 Theoretical value: 635.79; measured value: 635(M) + .

[0025] Cz (2.5g, 8.9mmol), intermediate product TBrBen (1.4g, 2.2mmol), Cu...

Embodiment 2

[0029] The structural formula is Synthesis of the second target compound:

[0030] In this example, the synthesis method of the intermediate product TbrBen is the same as that of Example 1 (the specific synthesis process is omitted).

[0031] Cz (2.5g, 8.9mmol), intermediate product TBrBen (2.8g, 4.5mmol), CuI (0.19g, 1.0mmol) and K 3 PO 4 (1.69g, 8.0mmol) was added into 100mL of toluene, and reacted for 24 hours under the protection of argon and reflux. After removal of the solvent, the residue was extracted three times with dichloromethane (3×100 mL), the organic phases were combined and dried over anhydrous magnesium sulfate, and the residue obtained by concentration was used as eluent with dichloromethane:n-hexane (7:3) on a column The product DCzCBr was purified by chromatography (2.7g, yield 50.3%). The intermediate product is identified and analyzed by a mass spectrometer, and the result is: mass spectrometry (MALDI-TOF): m / zC 65 h 64 Br 2 N 2 Theoretical value...

Embodiment 3

[0037] The blue-light organic electroluminescent material FIrpic is doped into the dichlorotoluene solution of the second target compound DCzCTpo (the mass fraction of DczCTpo is 8%), and it is configured into a solution whose total mass concentration (solute includes FIrpic and DCzCTpo) is 15mg / mL . Such as figure 1 As shown, 20 μL of the solution was dropped onto an indium tin oxide glass substrate, and an organic light-emitting layer film was prepared on a desktop homogenizer (KW-4A type) with a rotation speed of 1000 r / min and a spin coating time of 30 s. The thickness of the obtained organic film was measured to be about 50 nm.

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Abstract

The invention provides a tetraphenyl carbon-based OLED main body material and application thereof in preparation of an OLED device. The structural formula of the compound of the main body material isshown in the specification, wherein n of the four substituent groups R1, R2, R3 and R4 are the same electron donor groups, and 4-n of the four substituent groups R1, R2, R3 and R4 are same electron absorber groups; n is greater than or equal to 0 and less than or equal to 4. The tetraphenyl carbon-based OLED main body material provided in the invention can be used for preparing the OLED device through a solution process. The tetraphenyl carbon-based OLED main body material provided by the invention has controllable HOMO and LUMO energy levels to implement that a current carrier injects a luminous layer from an electrode or from a low-energy barrier or an energy-free barrier of a transmission layer of the current carrier, has singlet-state and triplet-state energy levels greater than 3.0 eVto effectively prevent the reduction of the performance of the device caused by the fact that an exciton is transmitted back from a luminous material to the main body material and improve the efficiency of the OLED device, and has a controllable hole and electron transmission rate to implement balance between electron transmission and hole transmission in the luminous layer and expand an excitoncombination region and a luminous region to reduce the roll-off of the efficiency of the OLED device.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a tetraphenyl carbon-based OLED host material and its application in preparing OLED devices. Background technique [0002] Organic light-emitting diodes (OLEDs) are the core components for the development of flat-panel displays, solid-state lighting and other fields due to their low cost, diverse materials, and ease of large-area fabrication. In order to meet the requirements of practical applications, the pursuit of "high efficiency and low cost" OLED materials and device preparation technology has always been the focus of research by researchers. It is well known that for organic electroluminescent materials, whether it is the first discovered organic fluorescent material, the most widely used organic phosphorescent material or the thermally activated delayed fluorescence (TADF) material developed in recent years, there is a phenomenon of aggregation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D219/02C07D209/86C07C211/54C07F9/53C07F9/572C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/54C07D209/86C07D219/02C07D401/14C07F9/5325C07F9/5728C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1044H10K85/631H10K85/6572H10K50/15H10K50/16H10K50/11H10K2102/00H10K2102/301
Inventor 杨叶子姚闯孙长庆
Owner YANGTZE NORMAL UNIVERSITY
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