Benzophenanthrene derivative and application thereof

A derivative, triphenylene technology, applied in triphenylene derivatives and their application fields, can solve the problems of reducing the quantum yield of the blue light system, poor color purity, low luminescence quantum efficiency, etc.

Active Publication Date: 2021-01-26
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, blue light materials still have the problems of low luminous quantum efficiency and poor color purity.
The main reason for this situation is that the blue light comes from the transition between energy levels with a wide energy gap, and organic compounds with wide band gaps have certain difficulties in molecular design, and secondly, there are strong blue light materials in the system. The π-π bond interaction has strong charge transfer characteristics, so that there are more non-radiative relaxation channels in the wide band gap, which intensifies the fluorescence quenching between molecules and reduces the quantum yield of the blue light system

Method used

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  • Benzophenanthrene derivative and application thereof
  • Benzophenanthrene derivative and application thereof
  • Benzophenanthrene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] The preparation method of compound CJHB271 comprises the following steps:

[0072] Step 1: Preparation of Compound Int.-1

[0073]

[0074] Under the protection of nitrogen, 24.5g (127.0mmol) of p-chlorobromobenzene was dissolved in 300mL of dry tetrahydrofuran, cooled to -78°C with liquid nitrogen, and 56.0mL of 2.5M n-butyllithium n-hexane solution was slowly added dropwise, and stirred React for 1 hour, add dropwise a solution of 19.5g (140.0mmol) of p-chlorobenzonitrile dissolved in 50mL of dry tetrahydrofuran, rise to room temperature and stir for 2 hours, add 50mL of saturated ammonium chloride aqueous solution, stir for 30 minutes, separate the organic phase, the water phase was extracted with ethyl acetate, the organic phase was collected and dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified with a silica gel column to obtain 27.7g of white solid, the yield was 87%.

[0075] The second step: the preparat...

Embodiment 2

[0090] The preparation method of compound CJHB387, comprises the steps:

[0091] The first step: preparation of compound Int.-5

[0092]

[0093] Under the protection of nitrogen, 12.8g (50.0mmol) of 2,7-dimethoxyxanth-9-one was dissolved in 200mL of dichloromethane, cooled to 0°C in an ice-water bath, and 20.0g of tetrabromide carbon and 12.5g of triisopropyl phosphite, stirred and reacted for 30 minutes, raised to room temperature and reacted for 1 hour, added dropwise 50mL of 1N dilute hydrochloric acid aqueous solution, stirred for 30 minutes, separated the organic phase, extracted the aqueous phase with dichloromethane, The organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain Int.-5 as a white solid with a yield of 94%.

[0094] The second step: the preparation of compound Int.-6

[0095]

[0096] Referring to the preparation method in the third step...

Embodiment 3

[0113] Preparation of compounds CJHB270~CJHB324, CJHB386, CJHB388~CJHB403:

[0114] Referring to the preparation method of Examples 1-2, only the diphenylamine in the fifth step in Example 1 or the 4,4'-dimethyldiphenylamine in the sixth step in Example 2 were replaced with different swollen amines, and other experimental parameters Make routine adjustments.

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PUM

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Abstract

The invention relates to a benzophenanthrene derivative and application thereof. The structural formula of the benzophenanthrene derivative is shown as a formula (I). The benzophenanthrene derivativeis a novel organic electroluminescent compound with a fused ring structure of indole, benzofuran and benzothienobenzophenanthrene, the intramolecular electron density is increased on the basis of benzophenanthrene, meanwhile, substituent groups are adjusted to increase the molecular steric hindrance, the pi-pi interaction between molecules is weakened, the internal quantum efficiency of moleculesis improved, and a shorter emission wavelength than conventional compounds is achieved. Meanwhile, the benzophenanthrene derivative hinders the generation of an organic intermolecular excitation-excitation compound and increases the internal electron density and stability, so that the effect and the service life of the organic electroluminescent device prepared from the benzophenanthrene derivative are obviously improved and prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a triphenylene derivative and an application thereof. Background technique [0002] Most of the substances used in organic electroluminescent elements are pure organic substances or organometallic complexes that form complexes between organic substances and metals. According to the application, they can be divided into hole injectors, hole transporters, luminescent substances, and electron transporters. , electron injectants, etc. Here, organic substances with relatively low ionization energy are mainly used as hole injectors or hole transporters, and organic substances with relatively high electronegativity are mainly used as electron injectors or electron transporters. In addition, the substance used as the luminescence assisting layer preferably satisfies the following characteristics. [0003] First, the materials used in organic electrolumine...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D495/04C07D487/04C07C211/61C07D493/16C07D495/16C07D491/16C07D311/94C07D251/24C07D493/06C07D495/06C07D487/06C09K11/06H01L51/50H01L51/54H01L51/42H01L51/46H01L51/05H01L51/30
CPCC07D493/04C07D495/04C07D487/04C07C211/61C07D493/16C07D495/16C07D491/16C07D311/94C07D251/24C07D493/06C07D495/06C07D487/06C09K11/06C09K2211/1014C09K2211/1011C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/624H10K85/631H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6576H10K85/6574H10K10/46H10K30/00H10K50/12Y02E10/549
Inventor 曹建华姜坤李程辉程友文王庆一赵佳王美艳孙建波
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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