Dibenzo-heterocyclic compound and preparation method and applications thereof

一种杂环化合物、二苯的技术，应用在有机电致发光材料领域，能够解决使用寿命缩短、器件发光效率降低、热稳定性低等问题

Inactive Publication Date: 2019-04-19
NINGBO LUMILAN NEW MATERIAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the technical problem to be solved by the present invention is to overcome the defects of low thermal stability and easy annihilation of excitons in the prior art, which reduce the luminous efficiency and shorten the service life of the device.

Method used

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  • Dibenzo-heterocyclic compound and preparation method and applications thereof
  • Dibenzo-heterocyclic compound and preparation method and applications thereof
  • Dibenzo-heterocyclic compound and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] This implementation provides a dibenzoheterocyclic compound, which has the structure shown in the following formula SP-01:

[0067]

[0068] The synthetic route of the dibenzoheterocyclic compound shown in formula SP-01 is as follows:

[0069]

[0070] The preparation method of the dibenzoheterocyclic compound shown in formula SP-01 comprises the following steps:

[0071] 1. Preparation of intermediate 1-1

[0072] Get 500 milliliters double-necked round-bottom flasks and put into stirrer bar and connect reflux pipe, fill with nitrogen after drying; First add compound A-1 (20.548 grams, 1.0 equivalent), NBS (N-bromosuccinimide , 19.578 grams, 1.1 equivalents), and AIBN (azobisisobutyronitrile, 0.821 grams, 0.5 mole percent), then add carbon tetrachloride (250 milliliters) and stir and mix for 10 minutes, and finally heat to reflux and react 24 hours; after it was warmed up, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), the resul...

Embodiment 2

[0083] This implementation provides a dibenzoheterocyclic compound, which has the structure shown in the following formula SP-02:

[0084]

[0085] The synthetic route of the dibenzoheterocyclic compound shown in formula SP-02 is as follows:

[0086]

[0087] The preparation method of the dibenzoheterocyclic compound shown in formula SP-02 comprises the following steps:

[0088] 1. Preparation of intermediate 1-2

[0089] Get 500 milliliters double-necked round-bottom flasks and put into stirrer bar and connect reflux tube, fill with nitrogen after drying; First add compound A-2 (20.548 grams, 1.0 equivalent), NBS (N-bromosuccinimide , 19.578 grams, 1.1 equivalents), and AIBN (azobisisobutyronitrile, 0.821 grams, 0.5 mole percent), then add carbon tetrachloride (250 milliliters) and stir and mix for 10 minutes, and finally heat to reflux and react 24 hours; after it was warmed up, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), the resul...

Embodiment 3

[0100] This implementation provides a dibenzoheterocyclic compound, which has the structure shown in the following formula SP-03:

[0101]

[0102] The synthetic route of the dibenzoheterocyclic compound shown in formula SP-03 is as follows:

[0103]

[0104] The preparation method of the dibenzoheterocyclic compound shown in formula SP-03 comprises the following steps:

[0105] 1. Preparation of Intermediates 1-3

[0106] Get 500 milliliters double-neck round-bottom flasks and put into stirrer bar and upper connection reflux tube, fill with nitrogen after drying; First add compound A-3 (20.548 grams, 1.0 equivalent), NBS (N-bromosuccinimide , 19.578 grams, 1.1 equivalents), and AIBN (azobisisobutyronitrile, 0.821 grams, 0.5 mole percent), then add carbon tetrachloride (250 milliliters) and stir and mix for 10 minutes, and finally heat to reflux and react 24 hours; after it was warmed up, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), t...

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Abstract

The invention discloses a dibenzo-heterocyclic compound, which has a structure represented by the formula (I). The LUMO energy level of the dibenzo-heterocyclic compound is low, the dibenzo-heterocyclic compound can be well matched with an electron transport material, and the electron injection and transportation are promoted. The dibenzo-heterocyclic compound has a good hole transport performance, is capable of balancing the ratio of electrons / holes in a luminous layer when being used as a luminous layer material, increases the compounding probability, and improves the luminous efficiency. Due to the spatial configuration of the dibenzo-heterocyclic compound, molecule stacking is avoided, the generation of high energy exciton generated by energy transmission between molecules is prevented, annihilation of exciton is inhibited, and the roll-off is inhibited. At the same time, the dibenzo-heterocyclic compound has good thermal stability and is capable of efficiently and stably emittingblue light. The invention also discloses an organic electroluminescent device, at least one functional layer of the device comprises the dibenzo-heterocyclic compound, and the blue light device has the advantages of high blue light luminous efficiency and low work voltage.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a dibenzoheterocyclic compound and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) are widely used in display and The field of lighting has great application prospects, and more and more people pay attention to it. [0003] In 1987, Tang et al. from Kodak Company of the United States prepared a multilayer OLED device by vacuum deposition coating method. OLED devices use conductive indium tin oxide (ITO) as the cathode, and sequentially vapor-deposit aromatic amine derivatives and tris(8-hydroxyquinoline)aluminum on it, and use magnesium-silver alloy as the anode material to obtain a high-brightness ( 1000cd / m 2 ) green light-emitting device. At the same time, due to the optimization of the device structure, a hole transport layer formed of aromatic amine derivatives is added to achieve higher lumin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07F7/18C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F7/0807C07F7/0816C07F7/0898C09K2211/1029C09K2211/1007C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1096H10K85/6565H10K85/654H10K85/6572H10K85/40H10K50/11C07F7/1804H10K85/1135H10K85/636H10K85/633H10K85/631C07F7/081C09K2211/1014H10K50/15H10K50/16H10K50/17H10K50/171H10K2101/30H10K2101/40
Inventor 魏定纬谢坤山陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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