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OLED material containing naphthophenanthridine structure, and applications thereof

A naphthophenanthridine and structural formula technology, applied in the field of OLED materials, can solve the problems of reducing the luminous efficiency of organic electroluminescent devices, electron and hole imbalance, and low glass transition temperature, so as to improve the exciton utilization rate, Effect of balanced injection, low turn-on voltage

Inactive Publication Date: 2018-08-03
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the triplet excited state energy of CBP is low (2.56eV). If doped with materials with high triplet excited state energy (greater than 2.65eV), the energy will be transferred back to the main light emitter, which will reduce the external quantum efficiency of the component. to 5.7%
The material N,N'-dicarbazole-3,5-substituted benzene (mCP) launched in 2003 has a low glass transition temperature, and the stability of the material itself is not high
In addition, mCP shows an imbalance between injected electrons and holes in the device, resulting in excess holes in the device and reducing the luminous efficiency of organic electroluminescent devices.

Method used

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  • OLED material containing naphthophenanthridine structure, and applications thereof
  • OLED material containing naphthophenanthridine structure, and applications thereof
  • OLED material containing naphthophenanthridine structure, and applications thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0043] Preparation of intermediate M-a

[0044]

[0045]In a 1L three-necked flask, add the raw material 1-(2-bromo-6-nitrophenyl)naphthalene (65.6g, 0.2mol), 250mL tetrahydrofuran, under the protection of nitrogen, cool down to the internal temperature -80~-70℃, start Add n-BuLi n-hexane solution (88mL, 2.5mol / L) dropwise, keep it at -80~-70°C for 2hrs, add dropwise 9hydro-4,5-diazafluorenone (36.0g, 0.2 mol) and 400mL tetrahydrofuran, after dripping, keep it at -80~-70℃ for 2hrs, continue to transfer the reaction system to room temperature for 1hrs, pour the reaction system into dilute hydrochloric acid (200g, 0.05mol / L) for hydrolysis 1hrs, acetic acid extraction with 500mL acetic acid, liquid separation, 350mL deionized water to wash the organic phase once, collect the organic phase, anhydrous Na 2 SO 4 Dry, filter, remove the solvent, and crystallize once with ethyl acetate and petroleum ether to obtain 73g of yellow solid with a yield of 85%, MS (m / s): 431.1.

[00...

Embodiment 1

[0063] Embodiment 1: the preparation of compound C01

[0064]

[0065] In a 100mL three-neck flask, add compound M-f (1.489g, 0.0025mol), 3-bromo-9-phenyl-9-hydrogen-carbazole (0.966g, 0.003mol), potassium carbonate (1.043g, 0.0075mol), Tetraphenylphosphine palladium (0.029g, 2.5×10 - 5 mol), water 20mL and toluene 50mL, under the protection of nitrogen, heat up to an internal temperature of 80-90°C, keep warm for 10hrs, cool down to room temperature, transfer the reaction solution to a 250mL separatory funnel to separate the lower aqueous phase, and the upper organic phase continues Wash with 150 mL of deionized water, remove the solvent, collect the solid, and purify by silica gel column chromatography, the eluent is dichloromethane:petroleum ether=1:5 (volume ratio), and further recrystallized and purified using toluene to obtain the compound 1.56 g of the crude product of C01 was further sublimated and purified using a chemical vapor deposition system at a sublimation...

Embodiment 2

[0066] Embodiment 2: the preparation of compound C02

[0067]

[0068] Using compound M-f and 2-chloro-4,6-diphenyl-1,3,5-triazine as raw materials, compound C02 was prepared according to the method described in Example 1, with a yield of 65.6%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 49 h 28 N 6 , the theoretical value is 700.2375, and the test value is 700.2359.

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Abstract

The invention discloses an OLED material containing a naphthophenanthridine structure, and applications thereof, and belongs to the technical field of organic electroluminescence, wherein the OLED material containing the naphthophenanthridine structure has the structure represented by a formula (1) defined in the specification. The invention further discloses applications of the OLED material containing the naphthophenanthridine structure in organic electroluminescence, and an organic electroluminescence device. According to the present invention, the OLED material containing the naphthophenanthridine structure has a certain carrier transporting capacity, appropriate molecular mass and suitable molecular energy level, and can be used as the phosphorescent host material in the field of organic electroluminescence.

Description

technical field [0001] The invention relates to an OLED material containing a naphthophenanthridine structure and an application thereof, belonging to the technical field of organic electroluminescence. Background technique [0002] Organic electroluminescent diode (OLED) is a very popular emerging flat display product at home and abroad. It has incomparable advantages such as liquid crystal display and plasma display, such as its own light emission, wide viewing angle, low working voltage and fast response speed. , short response time, thin panel, flexible display, etc., are considered to be the mainstream of next-generation display technology. [0003] According to the different light-emitting mechanisms of OLED devices, they can be divided into fluorescent devices and phosphorescent devices. But the theoretical value of the internal quantum efficiency of fluorescent light is only 25%, while the internal quantum efficiency of phosphorescent device can reach 100%. Therefo...

Claims

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Application Information

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IPC IPC(8): C07D471/20C07D519/00C07F7/08C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D471/20C07D519/00C07F7/0812C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1044C09K2211/1051C09K2211/1059C09K2211/1092C09K2211/1088H10K85/615H10K85/656H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K85/40H10K50/11
Inventor 王元勋吕公鑫张成新高自良朱政竹宋天资
Owner VALIANT CO LTD
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