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Spirobifluorene olefine organic electroluminescent material and preparation method thereof

A spirobifluorene olefin and luminescent material technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low luminous efficiency and short lifespan, and achieve high luminous efficiency, improved yield and good application value Effect

Inactive Publication Date: 2014-02-19
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the technical problems of low luminous efficiency and short service life of the existing blue-light organic luminescent materials, the present invention provides a spirobifluorene-based organic luminescent material with high luminous efficiency and long service life; and also provides a spirobifluorene-based organic luminescent material Preparation method of organic luminescent material

Method used

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  • Spirobifluorene olefine organic electroluminescent material and preparation method thereof
  • Spirobifluorene olefine organic electroluminescent material and preparation method thereof
  • Spirobifluorene olefine organic electroluminescent material and preparation method thereof

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Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: The specific synthetic route of compound 001 is as follows:

[0022]

[0023] (1) Under the condition of nitrogen protection, add 10ml of anhydrous tetrahydrofuran solution, 0.5g of magnesium bar, and 1 grain of iodine into the three-necked flask. After the Grignard reagent triggers, add 4.74g of 2,7-dibromospirobifluorene 10ml of tetrahydrofuran solution in water was reacted for 2 hours in an ice-water bath, 2ml of anhydrous N,N-dimethylformamide was added dropwise to the reaction solution, and then slowly raised to room temperature, and the reaction was continued for 3 hours. After adding 1M hydrochloric acid and 30ml ethyl acetate for liquid separation and extraction, the organic layer was washed with distilled water and saturated brine, dried over sodium sulfate, concentrated, and the resulting crude product was subjected to column chromatography (cyclohexane / dichloromethane=2 / 1), the resulting liquid was rotary evaporated and dried to obtain 2.98 ...

Embodiment 2

[0026] Embodiment 2: The specific synthetic route of compound 002 is as follows:

[0027]

[0028] (1) Under the condition of nitrogen protection, add 10ml of anhydrous tetrahydrofuran solution, 0.5g of magnesium bar, and 1 grain of iodine into the three-necked flask. After the Grignard reagent triggers, add 4.74g of 2,7-dibromospirobifluorene Water tetrahydrofuran solution (10ml) was reacted for 2.1 hours in an ice-water bath, 2ml of anhydrous N,N-dimethylformamide was added dropwise to the reaction solution, and then slowly raised to room temperature, and the reaction was continued for 3.2 hours. After adding 1M hydrochloric acid and 30ml ethyl acetate for liquid separation and extraction, the organic layer was washed with distilled water and saturated brine, dried over sodium sulfate, concentrated, and the resulting crude product was subjected to column chromatography (cyclohexane / dichloromethane=2 / 1), the resulting liquid was rotary evaporated and dried to obtain 2.98 ...

Embodiment 3

[0031] Embodiment 3: The specific synthetic route of compound 003 is as follows:

[0032]

[0033] (1) Under the condition of nitrogen protection, add 10ml of anhydrous tetrahydrofuran solution, 0.5g of magnesium bar, and 1 grain of iodine into the three-necked flask. After the Grignard reagent triggers, add 4.74g of 2,7-dibromospirobifluorene 10ml of water tetrahydrofuran solution was reacted for 2.2 hours under the condition of ice-water bath, and 2ml of anhydrous N,N-dimethylformamide was added dropwise to the reaction solution, then slowly raised to room temperature, and the reaction was continued for 3.4 hours. After adding 1M hydrochloric acid and 30ml ethyl acetate for liquid separation and extraction, the organic layer was washed with distilled water and saturated brine, dried over sodium sulfate, concentrated, and the resulting crude product was subjected to column chromatography (cyclohexane / dichloromethane=2 / 1), the resulting liquid was rotary evaporated and dri...

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Abstract

The invention relates to a spirobifluorene olefine organic luminescent material which is characterized in that the material has the following structural general formula shown in the specification, wherein the A group represents phenyl, biphenyl, naphthyl, aromatic amino, carbazolyl, substituted carbazolyl, N-phenyl, quinolyl, thiazolyl, thienyl, aromatic amino, azole-containing structural group, aromatic heterocyclic group, substituted aromatic heterocyclic group or aniline series group composed of 6-50 atoms. According to the invention, due to the introduction of double bonds, the material has better planar structure and conjugation system in comparison with simple spirobifluorene; electron transition regulates luminescence peak positions, thus obtaining the required light blue organic electroluminescent material; and the material has high luminescence efficiency, the luminescence efficiency in a dilute solution is about 95%, and the luminescence efficiency in a film can be up to about 62%.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, in particular to a spirobifluorene olefin organic light-emitting material and a preparation method thereof. Background technique [0002] As a flat panel display technology, organic electroluminescent devices have many advantages such as self-illumination, high brightness, wide viewing angle, ultra-thin, low energy consumption, fast response, rollable, full-color luminescence, etc., and have been favored by people. focus on. The performance of organic electroluminescent devices can be significantly improved by adopting appropriate device structure, device fabrication technology and organic materials. For example, in terms of full-color display, high-efficiency and stable green organic electroluminescent devices have reached the practical level. Compared with green organic electroluminescent devices, blue organic electroluminescent devices cannot fully meet the requirements of full-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C07D209/86C07C211/54C07C13/72C09K11/06H01L51/54
CPCC09K11/06C07C13/72C07C211/54C07D209/86C07D277/66C09K2211/1014C09K2211/1011C09K2211/1029C09K2211/1037H10K85/622H10K85/624H10K85/633H10K85/615H10K85/6572H10K85/657
Inventor 高春吉张英尹志超
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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