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Bi-fluoranthene-containing organic semiconductor material, its preparation method and application

An organic semiconductor, double fluoranthene technology, applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve the problems of poor solubility, poor film formation, and low yield, and achieve simple operation, Superior performance and easy processing results

Inactive Publication Date: 2013-06-19
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this structure still has some disadvantages, such as poor solubility, resulting in low yield, easy crystallization resulting in poor film formation, etc.

Method used

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  • Bi-fluoranthene-containing organic semiconductor material, its preparation method and application
  • Bi-fluoranthene-containing organic semiconductor material, its preparation method and application
  • Bi-fluoranthene-containing organic semiconductor material, its preparation method and application

Examples

Experimental program
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preparation example Construction

[0031] The preparation method of the above-mentioned bisfluoranthene-containing organic semiconductor material comprises the following steps:

[0032] S1, the structural formula is The 2,7-bistrimethylsilylacetylene-9,9-diR base fluorene, the structural formula is Trimethylsilylacetylene, catalyst and first solvent (such as, triethylamine, namely NEt 3 ) into the reactor without error, after heating and reflux reaction in an oil bath for 48h, the structural formula is generated as 2,7-ditrimethylsilylacetylene-9,9-dialkylfluorene; wherein, the reactor is an oxygen-free environment (that is, an inert atmosphere composed of at least one gas of nitrogen and argon), 2,7- The molar ratio of ditrimethylsilylacetylene-9,9-diR base fluorene to trimethylsilylacetylene is 1:3; the reaction formula is as follows:

[0033]

[0034] S2. Dissolve 2,7-ditrimethylsilylacetylene-9,9-dialkylfluorene in a mixed solvent containing tetrahydrofuran (THF) and methanol (MeOH), and then dropw...

Embodiment 1

[0050] This example discloses a fluorene-containing bisfluoranthene organic compound with the following structure: 2,7-bis(7,10-diphenylfluoranthene)-9,9-dimethylfluorene (D2PFMF)

[0051]

[0052] Step 1: Preparation of Compound A: 2,7-Ditrimethylsilylacetylene-9,9-Dimethylfluorene

[0053]

[0054] In a three-necked flask with nitrogen, add the catalyst Pd(PPh 3 ) 2 Cl 2 (630mg, 0.9mmol), CuI (45mg, 0.45mmol), 2,7-dibromo-9,9-dimethylfluorene (5.28g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), and 60mL triethylamine was used as a solvent, vacuumed three times with nitrogen gas, heated to reflux in an oil bath for 48h, washed with ether and filtered, the solvent was spin-off, and n-hexane was used as an eluent for silica gel column chromatography to obtain a light yellow solid (4.5, yield 78 %). MS: m / z386. 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 7.81 (d, 2H), 7.70 (d, 2H), 7.49 (t, 2H), 1.97 (s, 6H), 0.19 (s, 18H).

[0055] Step 2: Preparation of 2,7-bis(7,10-d...

Embodiment 2

[0061] This example discloses a fluorene-containing bisfluoranthene organic compound with the following structure: 2,7-bis(7,10-diphenylfluoranthene)-9,9-diethylfluorene (D2PFEF)

[0062]

[0063] Step 1: Preparation of Compound A: 2,7-Ditrimethylsilylacetylene-9,9-Diethylfluorene

[0064]

[0065] Into a three-necked flask with argon gas, add catalyst Pd(PPh 3 ) 2 Cl 2 (630mg, 0.9mmol), CuI (45mg, 0.45mmol), 2,7-dibromo-9,9-diethylfluorene (5.70g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), and 60mL of triethylamine was used as a solvent, evacuated and ventilated with argon for three times, heated and refluxed in an oil bath for 48h, washed with ether and filtered, the solvent was spin-off, and using n-hexane as an eluent for silica gel column chromatography to obtain a light yellow solid (4.97, the yield 80%). MS: m / z 414. 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 7.81 (d, 2H), 7.70 (d, 2H), 7.49 (t, 2H), 1.97 (q, 4H), 1.41 (t, 6H), 0.19 (s, 18H).

[0066] Step 2...

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Abstract

Belonging to the field of organic semiconductor materials, the invention discloses a bi-fluoranthene-containing organic semiconductor material, its preparation method and application. The bi-fluoranthene-containing organic semiconductor material has a chemical structural formula shown in the description, wherein R is linear chain alkyl of C1-C12. The fluorine-containing bi-fluoranthene organic semiconductor material provided in the invention has good solubility, and is easily dissolved in tetrahydrofuran, dichloromethane, toluene, chloroform and other common organic solvents, thus being easy to process. Because of the fluoranthene groups existing in the structure, the luminescent material has high hole mobility, and at the same time, the compound can emit pure blue light. Therefore, the material can form efficient and stable blue electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a bisfluoranthene-containing organic semiconductor material and its preparation method and application. Background technique [0002] In 1987, Tang and VanSlyke of Eastman Kodak Company in the United States reported a breakthrough in the research of organic electroluminescence. For the first time, they used the vacuum evaporation technology to combine the aromatic diamine with hole transport property and the 8-hydroxyquinoline aluminum (Alq) with high fluorescence efficiency and electron transport property. 3 ) combined to prepare a double-layer organic electroluminescent device. Under the driving voltage of 10V, the device emits green light with a brightness of up to 1000cd / m 2 , the efficiency reaches 1.5lm / W, and the life span exceeds 1000 hours. This milestone work has made people see a bright prospect for the practical and commercialization of organic electr...

Claims

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Application Information

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IPC IPC(8): C07C13/66C07C2/86C09K11/06H01L51/54
Inventor 周明杰王平
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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