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Double-fluoranthene organic semiconductor material as well as preparation method and application thereof

An organic semiconductor, double fluoranthene technology, applied in the field of double fluoranthene organic semiconductor materials and their preparation, can solve the problems of instability, high emission energy, low thermal stability and the like

Active Publication Date: 2013-04-03
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

Among the three primary colors, red and green light diodes are already close to the requirements of practical applications, but the blue light material has a wider band gap and a lower highest occupied orbital (HOMO) energy level, so there is a larger carrier injection energy. At the same time, blue light materials have high emission energy, are unstable, and are prone to energy transfer, resulting in impurity in emission color, so the development is relatively slow
However, the thermal stability of the existing blue light-emitting materials is not high, which limits the application of blue light-emitting materials

Method used

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  • Double-fluoranthene organic semiconductor material as well as preparation method and application thereof
  • Double-fluoranthene organic semiconductor material as well as preparation method and application thereof
  • Double-fluoranthene organic semiconductor material as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0042] The preparation method of the bisfluoranthene organic semiconductor material of one embodiment comprises the following steps:

[0043] Step S1, providing compound A and compound B (7,9-diphenyl-cyclopentenen-8-one) represented by the following structural formula:

[0044]

[0045] Among them, -R is -CN, -NO 2 、-CF 3 , -F or -CHO,

[0046]

[0047] Wherein, the preparation process of compound A comprises the following steps:

[0048] First, compound D represented by the following structural formula is provided,

[0049]

[0050] Among them, -R is -CN, -NO 2 、-CF 3 , -F, or -CHO.

[0051] Secondly, under an inert gas atmosphere, compound D and trimethylsilylacetylene are added to the solvent in a molar ratio of 1:3 to 1:3.2, and after adding the catalyst, react at reflux temperature and purify to obtain compound A. The catalyst is organic palladium Cocatalyst with cuprous iodide.

[0052] In this embodiment, the molar ratio of organic palladium and cuprou...

Embodiment 1

[0067] This example prepares 4,4'-(7,10-diphenylfluoranthenyl)-4"-cyanotriphenylamine (D2PFCTPA)

[0068] Include the following steps:

[0069] Step S11, preparing 4,4'-trimethylsilylacetylene-4"-cyanotriphenylamine (compound A).

[0070] In a three-necked flask with nitrogen, add the catalyst Pd(PPh 3 ) 2 Cl 2 (630mg, 0.9mmol), CuI (45mg, 0.45mmol), 4,4'-bromo-4"-cyanotriphenylamine (6.39g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), in 60mL Triethylamine was used as a solvent, and nitrogen gas was evacuated three times, and the oil bath was heated and refluxed for 48h. The reaction solution was washed with ether and filtered, the solvent was spin-off, and n-hexane was used as the eluent for silica gel column chromatography to obtain a light yellow solid (5.41g, Yield 78%).

[0071] The reaction formula is as follows:

[0072]

[0073] 4,4'-trimethylsilylacetylene-4"-cyanotriphenylamine H NMR test results are as follows:

[0074] 1 H NMR (400MHz, CD 2 Cl 2 ...

Embodiment 2

[0091] This example prepares 4,4'-(7,10-diphenylfluoranthenyl)-4"-trifluoromethyltriphenylamine (D2PFTFTPA)

[0092] Include the following steps:

[0093] Step S21. Preparation of 4,4'-trimethylsilylacetylene-4"-trifluoromethyltriphenylamine (compound A).

[0094] Into a three-necked flask with argon gas, add catalyst Pd(PPh 3 ) 4 (1038mg, 0.9mmol), CuI (45mg, 0.45mmol), 4,4'-bromo-4"-trifluoromethyltriphenylamine (7.06g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), Using 60mL triethylamine as solvent, vacuum three times with nitrogen gas, heat and reflux in an oil bath for 48h, wash with ether and filter, spin off the solvent, use n-hexane as eluent for silica gel column chromatography, and obtain a light yellow solid (6.06g, produced rate 80%).

[0095] The reaction formula is as follows:

[0096]

[0097] 4,4'-trimethylsilylacetylene-4"-trifluoromethyltriphenylamine proton nuclear magnetic resonance spectrum test results are as follows:

[0098] 1 H NMR (400M...

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Abstract

The invention relates to a double-fluoranthene organic semiconductor material. The double-fluoranthene organic semiconductor material can be shown as a structural formula described in the specification, wherein -R is -CN, -NO2, -CF3, -F or -CHO. The double-fluoranthene organic semiconductor material emits pure blue lights, the double-fluoranthene organic semiconductor material can be easily dissolved in common organic solvents such as tetrahydrofuran, dichloromethane, methylbenzene and chloroform as an electron withdrawing group is introduced into the structure, and solubility and film-forming property of the double-fluoranthene organic semiconductor material are improved; meanwhile, a fluoranthene group is a rigid substituent group, so that the double-fluoranthene organic semiconductor material also has excellent thermal stability; the fluoranthene group can cause the double-fluoranthene organic semiconductor material to have higher hole mobility; and electro transport performance of the double-fluoranthene organic semiconductor material is improved as the electron withdrawing group is introduced, so that carrier transport balance is facilitated. The invention also provides a preparation method of the double-fluoranthene organic semiconductor material and an application of the double-fluoranthene organic semiconductor material in an organic electroluminescence device.

Description

【Technical field】 [0001] The invention relates to the field of optoelectronics, in particular to a bisfluoranthene organic semiconductor material and its preparation method and application. 【Background technique】 [0002] In recent years, organic light-emitting diodes (OLEDs) have made great progress. Among the three primary colors, red and green light diodes are already close to the requirements of practical applications, but the blue light material has a wider band gap and a lower highest occupied orbital (HOMO) energy level, so there is a larger carrier injection energy. At the same time, blue light materials have high emission energy, are unstable, and are prone to energy transfer, resulting in impure emission colors, so the development is relatively slow. However, the thermal stability of the existing blue light-emitting materials is not high, which limits the application of blue light-emitting materials. 【Content of invention】 [0003] Based on this, it is necessar...

Claims

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Application Information

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IPC IPC(8): C07C255/58C07C253/30C07C211/56C07C209/68C07C223/06C07C221/00C09K11/06H01L51/54
Inventor 周明杰王平
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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