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Fluorenyl aromatic phosphine oxide photoelectric material and preparation method thereof

A technology of aromatic phosphine oxide and optoelectronic materials, applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of poor electron injection and transmission performance, unbalanced carrier injection and transmission, etc., and achieve the suppression of triplet-triplet annihilation , Inhibit concentration quenching, and maintain the effect of blue light emission performance

Inactive Publication Date: 2013-02-13
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the technical problem that the aromatic hydrocarbon or aromatic amine functional group with a large conjugated structure is introduced into the fluorene system, because the electron injection and transport performance of this functional group is very poor, resulting in unbalanced carrier injection and transport, the present invention provides A kind of fluorenyl aromatic phosphine oxide photoelectric material and its preparation method

Method used

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  • Fluorenyl aromatic phosphine oxide photoelectric material and preparation method thereof
  • Fluorenyl aromatic phosphine oxide photoelectric material and preparation method thereof
  • Fluorenyl aromatic phosphine oxide photoelectric material and preparation method thereof

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specific Embodiment approach 2

[0023] Specific embodiment two: the preparation method of the fluorenyl aromatic phosphine oxide photoelectric material in this embodiment is carried out according to the following steps:

[0024] 1. Dissolve 1mmol 9,9-bis-(diphenylphosphinoxyphenyl)fluorene in a mixture of 2-10mL glacial acetic acid and 1-8mL concentrated sulfuric acid, and then add 0.5-3mmol N-bromosuccinate imide, extraction, drying, and column chromatography to obtain 2-bromo-(9,9-bis-(diphenylphosphinoxyphenyl))fluorene;

[0025] 2. Add 1mmol 2-bromo-(9,9-bis-(diphenylphosphineoxyphenyl))fluorene, 0.005-0.1mmol tetrakis(triphenylphosphine)palladium, 0.01-0.1mmol tetrabutylammonium bromide Mix with 0.5-2mmol borate, then add 3-15mL tetrahydrofuran to dissolve under the condition of argon protection and avoid light, then add 3mL-10mL NaOH solution with a concentration of 2mol / L, and react at 80-90℃ for 8-32h , extracted with saturated ammonium chloride solution, dried, and column chromatographed to obtain ...

specific Embodiment approach 3

[0026] Specific embodiment three: the difference between this embodiment and specific embodiment two is that the borate described in step two is diethylfluorene borate, phenylcarbazole borate, triphenylamine borate or naphthyl Phenylamine borate. Others are the same as in the second embodiment.

specific Embodiment approach 4

[0027] Embodiment 4: The preparation method of fluorenyl aromatic phosphine oxide photoelectric material in this embodiment is carried out according to the following steps:

[0028] 1. Dissolve 1mmol 9,9-bis-(diphenylphosphinoxyphenyl)fluorene in a mixture of 2-10mL glacial acetic acid and 1-8mL concentrated sulfuric acid, and then add 0.5-3mmol N-bromosuccinate imide, extraction, drying, and column chromatography to obtain 2-bromo-(9,9-bis-(diphenylphosphinoxyphenyl))fluorene;

[0029] Two, 1mmol 2-bromo-(9,9-bis-(diphenylphosphineoxyphenyl)) fluorene, 1-6mmol potassium carbonate, 1-10mmol carbazole, 0.05-0.5mmol cuprous iodide and 0.001- 0.05mmol 18-crown-6-ether, under nitrogen protection, add 3-10mL 3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, react at 90-250°C for 12-50h, Extract, dry, and column chromatography to obtain a fluorenyl aromatic phosphine oxide photoelectric material.

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Abstract

The invention relates to a photoelectric material and a preparation method thereof, particularly to a fluorenyl aromatic phosphine oxide photoelectric material and a preparation method thereof, and aims at solving the problem that carrier injection transmission is unbalanced caused by the fact that aromatic hydrocarbon or arylamine functional groups with large conjugated structures are introduced into a fluorine system. The method includes preparing 2-bromine-(9,9-bis-(diphenylphosphine oxide) ) fluorine; and mixing the 2-bromine-(9,9-bis-(diphenylphosphine oxide) ) fluorine, tetrakis (triphenylphosphine) palladium, tetrabutylammonium bromide and borate and dissolving in tetrahydrofuran, adding in NaOH solution, and obtaining the photoelectric material after reaction, extraction, drying and column chromatography; or mixing the 2-bromine-(9,9-bis-(diphenylphosphine oxide) ) fluorine, carbazole, potassium carbonate, copper iodide and 18-crown-6-ether, adding in a high-temperature solvent, and obtaining the photoelectric material after reaction, extraction, drying and column chromatography. The power efficiency of the photoelectric material prepared through the method can reach 2.19lm / W when the material is used for preparing blue-ray fluorescent devices.

Description

technical field [0001] The invention relates to a photoelectric material and a preparation method thereof. Background technique [0002] Organic electroluminescent materials and display devices have attracted extensive attention since their appearance due to their light weight, thin thickness, low driving voltage, fast response speed, and wide viewing angle range. Organic electroluminescent materials and devices have become a research hotspot. . [0003] Fluorene has the advantages of easy modification, wide energy gap, and high luminous efficiency. Therefore, it plays an important role in OLED materials, especially blue light materials. However, fluorene has low affinity, poor solubility, and is easily oxidized to fluorenone defects, which seriously affects the efficiency of devices. At present, multiple modification methods are usually used to improve the performance of fluorene materials. Although the simple oligomer or spirofluorene structure improves the thermodynami...

Claims

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Application Information

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IPC IPC(8): C07F9/53C07F9/572C09K11/06H01L51/54
Inventor 许辉于东慧
Owner HEILONGJIANG UNIV
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