A tetraphenyl carbon-based oled host material and its application in the preparation of oled devices

A main material, tetraphenyl carbon technology, applied in the direction of electric solid device, semiconductor device, organic semiconductor device materials, etc., can solve the problems of wide energy band gap and OLED main material can not have at the same time

Inactive Publication Date: 2020-07-07
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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  • A tetraphenyl carbon-based oled host material and its application in the preparation of oled devices
  • A tetraphenyl carbon-based oled host material and its application in the preparation of oled devices
  • A tetraphenyl carbon-based oled host material and its application in the preparation of oled devices

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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 host material and its application in OLED devices. The compound structural formula of the host material is wherein, R 1 , R 2 , R 3 and R 4 Among the four substituents, n are the same electron-donating group, 4-n are the same electron-withdrawing group, 0≤n≤4; the tetraphenyl carbon-based OLED host material provided by the present invention can be used for Solution method to prepare OLED devices. The tetraphenyl carbon-based OLED host material provided by the present invention has controllable HOMO and LUMO energy levels, which can realize low energy barrier or no energy barrier injection of carriers from the electrode or carrier transport layer into the light emitting layer; The singlet and triplet energy levels can effectively prevent the excitons from back-transporting from the light-emitting material to the host material and reduce the performance of the device, which can improve the efficiency of the OLED device; with adjustable hole and electron transport rates, the light-emitting layer can be realized The balance of electron and hole transport in the medium, extending the exciton recombination region and light emitting region to reduce the roll-off of OLED device efficiency.

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 Patents(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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