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Compound containing phosphorous oxy-group and pyridine unit, and method for preparing same

A compound, phosphorus-oxygen technology, applied in the field of organic electroluminescence, the field of preparation of compounds containing phosphorus-oxygen and pyridine units, can solve problems such as insufficient electron transport capacity, achieve improved luminous efficiency, and simple synthesis method Effect

Inactive Publication Date: 2012-09-19
东莞彩显有机发光科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The electron transport materials commonly used in phosphorescent systems are mainly nitrogen-containing heterocyclic materials such as pyridine, because they have good electron transport capabilities, but only good electron transport capabilities are not enough, and a higher triplet energy level is required to Confining the escape of triplet excitons from the emissive layer

Method used

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  • Compound containing phosphorous oxy-group and pyridine unit, and method for preparing same
  • Compound containing phosphorous oxy-group and pyridine unit, and method for preparing same
  • Compound containing phosphorous oxy-group and pyridine unit, and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] An electron transport material with a high triplet energy level, namely 3,3',3'',3'''-(5,5'-(phenylphosphoroxy)bis(benzene-5,3,1) -3)) The preparation method of tetrapyridine, the reaction process is as follows:

[0041]

[0042] The specific reaction steps are:

[0043] 1. Preparation of the initial product 4,4'-(5-bromo-1,3-diphenyl)dipyridine: Weigh 5g 1,3,5-tribromobenzene, 4.88g pyridine-4-boronic acid, 0.73g Pd (PPh 3 ) 4 , 20ml 2M K 2 CO 3 , 20ml ethanol, 80ml toluene were added to a 250ml three-necked flask, heated to 95 ℃, nitrogen protection. After 21 hours of reaction, the reaction was stopped, the reaction solution was poured into water, the organic layer was separated, the aqueous layer was extracted three times with dichloromethane, the organic layers were combined, the organic layer was washed with saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. It was filtered the next morning, and the filtrate was spin-dried with a rotary...

Embodiment 2

[0054] LUMO and HOMO energy level analysis of compound 1

[0055] Perform UV absorption, fluorescence emission and cyclic voltammetry tests on compound 1, from Figure 4 In the cyclic voltammetry spectrum, the HOMO of compound 1 is 6.61eV, and then from image 3 The UV absorption and fluorescence emission spectra show that the LUMO of compound 1 is 2.4 eV, which can prove that compound 1 has better electron affinity and ion potential.

Embodiment 3

[0057] An electron transport material with a high triplet energy level is used in a blue phosphorescent device. The electron transport material is composed of a phosphoroxy group with a high triplet energy level and a pyridine unit with electron transport capability.

[0058] The phosphorescent host material with bipolar carrier transport ability uses ITO as the anode, HAT as the hole injection material, NPB as the hole transport material, mCP as the electron blocking material, and compound 1， That is, the final product prepared in Example 1 of the present invention is an electron transport material, FIrpic is a blue-doped luminescent material, and 2,6-DCzPPY is a host material ， LiF is an electron injection material, Al is a cathode, and a device is prepared. Among them,

[0059] Device structure ( Image 6 ) Is: ITO / HAT(20nm) / NPB(30nm) / mcp(5nm) / 2,6-DCzPPY: FIrpic(8wt%,30nm) / compound 1 (20nm) / LiF(1nm) / Al(100nm);

[0060] Table 1: Reported materials and materials of the p...

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Abstract

The invention relates to a compound containing a phosphorous oxy-group and a pyridine unit, and a method for preparing the same. The compound is composed of a phosphorous oxy-group with high triplet state and a pyridine unit having electron transfer capability; the structural formula of the compound is as shown in the specification, wherein R1 and R2 are phenyls or six-member nitrogen-bearing heterocyclic rings. The method for preparing the compound comprises the following steps of: firstly, evenly mixing compounds containing benzene and pyridine in a mol ratio of 1: (2-3) and arousing a chemical reaction, thereby obtaining a compound containing the phenyl and the pyridine; secondly, reacting the compound containing the phenyl and the pyridine with phenyl phosphorus in an organic solution in a mol ratio of 1: (0.4-0.5), thereby obtaining a compound containing the phenyl phosphorus and the pyridine unit; and finally, reacting the compound containing the phenyl phosphorus and the pyridine unit with hydrogen peroxide in a mol ratio of 1: (5-10), thereby obtaining the compound containing the phosphorous oxy-group and the pyridine unit. The method provided by the invention is rich in raw material source, convenient for synthesis, high in yield and suitable for large-scale production; and the material prepared by the method has high efficiency on electron transfer of phosphorescent and blue light systems.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to a method for preparing a compound containing phosphorus oxygen and pyridine units, and the application of the material prepared according to the method in the field of organic electroluminescence. Background technique [0002] In the past two decades, organic electroluminescent devices (OLEDs) have been widely used due to their advantages such as self-luminescence, high brightness, high efficiency, thinness, wide viewing angle, easy processing, low voltage drive, easy large-area preparation, and full-color display. Its application prospects have attracted widespread attention. The research on organic luminescence began in the 1950s. Until 1987, Tang et al. of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the developed OLED device had a luminance of 1000cd / m2 driven by a DC voltage of 10V. 2 , so that OLED ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/58H01L51/54
Inventor 殷正凯颜培坚吴志达
Owner 东莞彩显有机发光科技有限公司
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