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Organic semiconductor material based on fluorene, anthracene and quinoxaline, preparation method thereof and application thereof

An organic semiconductor and quinoxaline technology, which is applied in the field of organic semiconductor materials and their preparation, can solve problems such as limiting the scope of application, and achieve the effects of wide light absorption range, improved carrier mobility and light absorption range, and high yield

Active Publication Date: 2012-03-14
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

Although there have been many reports on anthracene and its derivatives as organic electroluminescent materials, there are few reports on organic photovoltaic materials, which greatly limits its application range.

Method used

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  • Organic semiconductor material based on fluorene, anthracene and quinoxaline, preparation method thereof and application thereof
  • Organic semiconductor material based on fluorene, anthracene and quinoxaline, preparation method thereof and application thereof
  • Organic semiconductor material based on fluorene, anthracene and quinoxaline, preparation method thereof and application thereof

Examples

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preparation example Construction

[0039] A method for preparing an organic semiconductor material based on fluorene, anthracene and quinoxaline, the steps are as follows:

[0040] Step 1, in an anhydrous and oxygen-free environment, mix 2,7-dibromo-9,9-dialkylfluorene and n-butyllithium at -70°C to -85°C in a molar ratio of 1.0:2.0 to 1.0:4.0 Add to the second solvent, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (or bispinacol diborane) , carry out condensation reaction 12~48 hours, obtain 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dialkyl Fluorene; wherein, the second solvent is at least one of tetrahydrofuran, ether, dichloromethane, chloroform or ethyl acetate; 2-isopropoxy-4,4,5,5-tetramethyl-1, The molar weight of 3,2-dioxaborolane is 2 to 4 times that of 2,7-dibromo-9,9-dialkylfluorene;

[0041] The condensation reaction formula is as follows:

[0042]

[0043] In the formula, m is an integer greater than or equal to 1 and less than or equal to 20;

[0044] Step 2, in an o...

Embodiment 1

[0056] This embodiment discloses organic semiconductor materials P1 and P2 based on fluorene, anthracene and quinoxaline with the following structures:

[0057]

[0058] The preparation steps of P1 and P2 are as follows:

[0059] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0060]

[0061] Set up an anhydrous and anaerobic reaction device, stirring and N 2 Under the protection of the three-necked flask, add 9.0mmol of white 2,7-dibromo-9,9-dioctylfluorene, inject 150ml of refined tetrahydrofuran solvent with a syringe, and then slowly inject it with a syringe at -78°C 27.0mmol n-BuLi, stirred for 2 hours. After reacting for 2 hours, inject 30.6mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with a syringe under the condition of -78°C, and heat up to React overnight at room temperature, and the reaction time is about 12-18 hours.

[0062] After the reaction, add saturated NaCl aqueous solution, extract with ch...

Embodiment 2

[0070] This embodiment discloses organic semiconductor materials P3 and P4 based on fluorene, anthracene and quinoxaline with the following structures:

[0071]

[0072] The preparation steps of P3 and P4 are as follows:

[0073] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dihexylfluorene:

[0074] For the preparation process, refer to Step 1 in Example 1, except that argon is used to construct an oxygen-free environment protection atmosphere.

[0075] Step 3, preparation of P3 and P4:

[0076]

[0077] Add 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dihexylfluorene 1mmol, 9, 10-dibromo-2,6-di(2-octyldecyl)anthracene 0.8mmol (see Macromol.Chem.Phys.2006, 207, 1107-1115 for the synthesis method of this compound), 2,3-dimethyl- 5,8-bis(5-bromothienyl)quinoxaline 0.2mmol, Pd(OAc) 2 3mg, 2mol / L Na 2 CO 3With 10ml of aqueous solution and 40ml of toluene solvent, the reaction system is in an oxygen-free state by repeatedly passing a...

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Abstract

The invention discloses an organic semiconductor material based on fluorene, anthracene and quinoxaline, a preparation method thereof and an application thereof. The organic semiconductor material has a structure represented by formula (P). In the formula (P), n is an integer greater than 1 and equal to or less than 200, and m is an integer equal to or greater than 1 and equal to or less than 20;x and y are positive real numbers, and the value of x+y is 1; R1 and R2 are hydrogen, fluorine, cyan, C1-C40 alkyl, alkoxy, aryl, or heteroaryl respectively; and R3 is hydrogen, phenyl, C1-C20 alkyl,or C1-C40 arylalkoxy. The organic semiconductor material based on fluorene, anthracene and quinoxaline of the invention, which has a high carrier mobility, a strong absorbance, and a wide light absorption range, allows the sunlight utilization rate to be improved; and the preparation method of the organic semiconductor material, which has the advantages of simple technology and high yield, is easy to operate and control.

Description

【Technical field】 [0001] The invention relates to the field of optoelectronics, in particular to an organic semiconductor material based on fluorene, anthracene and quinoxaline, a preparation method and application thereof. 【Background technique】 [0002] High-efficiency solar cells are usually made of inorganic semiconductors, but the main silicon solar cells currently on the market are complicated in the production process, serious in pollution, high in energy consumption, and high in cost, which inhibits the development of its commercial application. Therefore, the preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. On the one hand, organic semiconductor materials have good environmental stability, low preparation cost, easy function modulation, good flexibility and film-forming properties; on the other hand, organic solar cells have relatively simple processing and ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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