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An electron injection material and an organic light-emitting device

An electron injection material, an unsubstituted technology, applied in the field of electron injection materials and organic light-emitting devices, can solve the problems of inferior injection properties as alkali metals, bottlenecks in transfer efficiency, life of cracking devices, etc., and achieve molecular stability, high electron injection capability, Combining simple effects

Active Publication Date: 2022-02-11
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the weakness of the Liq system is that its transfer efficiency has a bottleneck, causing its injection characteristics to be inferior to those of alkali metals; moreover, the thermodynamic properties of Liq are a very big test on the G6 production line. Prolonged heating will inevitably crack Liq thereby affecting device lifetime
Alkali metals are too active. Although they have good injection characteristics, they are unstable in the atmosphere and are prone to combustion and accidents. Therefore, there are great safety hazards in factories.

Method used

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  • An electron injection material and an organic light-emitting device
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  • An electron injection material and an organic light-emitting device

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preparation example Construction

[0090] The present invention also provides a preparation method of the above-mentioned electron injection material, comprising: reacting the compound represented by formula (II) with the compound represented by formula (III) to obtain R 1 with R 2 Compounds represented by formula (I) having the same substituent;

[0091] Alternatively, the compound shown in formula (II) is first reacted with the compound shown in formula (III), and then reacted with the compound shown in formula (IV), to obtain R 1 with R 2 Compounds shown in formula (I) with different substituents;

[0092] Alternatively, the compound shown in formula (II) is first reacted with the compound shown in formula (IV), and then reacted with the compound shown in formula (III) to obtain R1 with R 2 Compounds represented by formula (I) having different substituents.

[0093]

[0094] Wherein, X is a halogen, preferably Br; the R 1 with R 2 All are the same as above, and will not be repeated here.

[0095] T...

Embodiment 1

[0109] The preparation method of the electron injection material M1 comprises the following steps:

[0110] (1)

[0111] Add 100 g (714.28 mmol) of compound 1 into a 3 L three-necked flask, add 1 L ether solution, and stir. Then measure 76.46mL (1499.98mmol) of bromine into the constant pressure dropping funnel, seal the liquid surface of bromine with 10mL of water, slowly add it dropwise into the reaction solution, and stir at room temperature for 6h after the dropwise addition is completed. After the reaction was over, 500 mL of saturated NaCl was added to the reaction solution to quench the reaction, then the organic phase was extracted with dichloromethane (1 L), and the organic phase was then washed with saturated NaHSO 3 Extract twice, and finally extract once with saturated saline. Collect the organic phase and add anhydrous magnesium sulfate to stir, filter, collect the filtrate to remove the solvent by rotary evaporation, and purify the product by column chromatog...

Embodiment 2

[0121] The preparation method of electron injection material M11 comprises the following steps:

[0122]

[0123] Add 20 g (67.13 mmol) of compound A and 33.11 g (140.9 mmol) of compound 2 into a three-necked flask in turn, add 200 mL of toluene solution, and stir well. Nitrogen replacement was performed three times, and 0.15 g (6.713 mmol) of palladium acetate and 19.44 g (140.9 mmol) of potassium carbonate were added under a nitrogen atmosphere. After the addition, nitrogen replacement was performed three times, and stirred at 120° C. for 6 h. Cool to room temperature at the end of the reaction, and use 200mL saturated NaHSO 3 The reaction was quenched, and the organic phase was extracted with dichloromethane (150 mL), and the organic phase was then washed with saturated NaHSO 3 Extract twice, and finally extract once again with saturated saline, collect the organic phase and add anhydrous magnesium sulfate to stir, filter, collect the filtrate and rotary evaporate to re...

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Abstract

The present invention provides an electron injection material, as shown in formula (I); wherein, the R 1 with R 2 Each independently is a substituted or unsubstituted alkylamino group, a substituted or unsubstituted heterocyclic group, and a derivative group thereof. Compared with the prior art, the adamantane organic base provided by the present invention takes amantadine as the core, and at the same time connects a structure capable of transporting electrons as an electron injection material, which can form a hydrogen bond with the electron transport material to achieve high electron density. Injection ability, it does not need to consider ionization energy, and the synthesis of the electron injection material is simple, the molecule is stable, while ensuring the formation of hydrogen bonds, the molecule also has flexible branched chains, which is convenient to make inkjet materials, not only can be used for direct vapor deposition Coating can also be used to make devices in the form of inkjet, which helps to reduce costs.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to an electron injection material and an organic light emitting device. Background technique [0002] In recent years, the application of various new organic semiconductor materials and new organic semiconductor device structures has made significant progress in OLED performance and industrialization. Compared with traditional inorganic semiconductor materials, organic semiconductor materials have obvious advantages. However, the carrier concentration and mobility of organic semiconductor materials, especially electron transport materials, are relatively low, and the mobility of electrons in organic semiconductor materials is generally lower than that of holes, such as figure 1 As shown in (a), the injection and transport of electrons in OLEDs is more difficult than that of holes, so electrons and holes cannot be completely recombined in the recombination reg...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07D519/00H01L51/00H01L51/54
CPCC07D487/22C07D519/00H10K85/654H10K85/6572H10K85/657H10K50/171
Inventor 潘龙鑫张正川代好叶添昇汪奎
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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