Organic semiconductor material, preparation methods and uses thereof

An organic semiconductor and organic technology, applied in the preparation of organic semiconductor materials, organic semiconductor materials containing fluorene, can solve the mismatch between device spectral response and solar radiation spectrum, low carrier mobility of organic semiconductor devices, inorganic solar cells Low conversion efficiency and other issues, to achieve the effect of wide light absorption range, excellent solubility and charge transport performance, and improve carrier mobility

Inactive Publication Date: 2015-01-07
OCEANS KING LIGHTING SCI&TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although organic solar cells have developed rapidly, their conversion efficiency is still much lower than that of inorganic solar cells. The main constraints that limit the improvement of their performance are: the relatively low carrier mobility of organic semiconductor devices, the spectrum of devices The response does not match the spectrum of solar radiation, the red light region with high photon flux is not effectively utilized, and the electrode collection efficiency of carriers is low, etc.

Method used

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  • Organic semiconductor material, preparation methods and uses thereof
  • Organic semiconductor material, preparation methods and uses thereof
  • Organic semiconductor material, preparation methods and uses thereof

Examples

Experimental program
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preparation example Construction

[0036] The present invention also provides a method for preparing the above-mentioned organic semiconductor material, comprising the following steps:

[0037]Step S1. In an anhydrous and oxygen-free environment, mix 2,7-dibromo-9,9-dialkylfluorene and n-butyllithium (n-BuLi) at -70°C to -85°C at a molar ratio of 1.0: 2.0~1.0: Add 4.0 to the first solvent, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (or bispina Alcohol diboron) (the molar amount is 2.0 to 4.0 times that of 2,7-dibromo-9,9-dialkylfluorene), warming up to 20-30°C, and reacting for 12-48 hours to obtain the product, namely 2 ,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dialkylfluorene; wherein, the first solvent is tetrahydrofuran, diethyl ether , dichloromethane, chloroform or ethyl acetate, etc.; its reaction formula is as follows:

[0038]

[0039] In the formula, m is a natural number, and 1

[0040] Step S2. In an oxygen-free environment, 2,7-bis(4,4,5,5-...

Embodiment 1

[0054] Example 1 This example discloses organic semiconductor materials P1 and P2 with the following structures:

[0055]

[0056] The preparation steps of P1 and P2 are as follows:

[0057] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0058]

[0059] Set up an anhydrous and anaerobic reaction device, stirring and N 2 Under the protection of the three-necked bottle, 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 2 hours, inject 30.6 mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with a syringe at -78°C, and raise the temperature to 22 °C, react for 14 hours.

[0060] After the reaction, add saturated NaCl aqueous solution, extract with chloroform, dry over anhydrous sodium sulfate, collect the filtrate after filtration and rotary evaporate the so...

Embodiment 2

[0067] Example 2 This example discloses organic semiconductor materials P3 and P4 with the following structures:

[0068]

[0069] The preparation steps of P3 and P4 are as follows:

[0070] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dihexylfluorene:

[0071] Its preparation process refers to the step one difference in Example 1 in that:

[0072]In step S1, the temperature is -75°C, the temperature is raised to 20°C, and the reaction time is 48 hours; the molar ratio of 2,7-dibromo-9,9-dihexylfluorene to n-butyllithium is 1:2; the solvent is dichloromethane; The molar amount of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is 2,7-dibromo-9,9-dihexylfluorene mole 3 times the amount. .

[0073] Step 3, preparation of P3 and P4:

[0074]

[0075] Add 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan) base-9,9-dihexylfluorene 1mmol, 9, 10-dibromo-2,6-bis(2-octyldecyl)anthracene 0.8mmol (see Macromol.Chem.Phys.2006,207,1107-1115 of Kl...

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Abstract

Disclosed are organic semiconductor material, preparation methods and uses thereof. The organic semiconductor material is shown as the following formula (P), in which R 1 , R 2 , R 3 , m, n, x and y are defined as the description. The said organic semiconductor material can be used in organic solar cell, organic field effect transistor, organic electroluminescence element, organic optical storage, organic non-linear material or organic laser element.

Description

technical field [0001] The invention relates to an organic semiconductor material, more specifically to an organic semiconductor material containing fluorene. The invention also relates to a preparation method and application of the organic semiconductor material. 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 cell...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14C07C13/567C07C13/573C09K11/06
CPCC09K2211/1011C07D495/14C07F5/025C08G2261/124C08G2261/411C08G2261/3142C08G2261/91C08G2261/314C08G2261/1412C09K2211/1037C09K2211/1416C08G61/124C07D519/00C08G2261/3243C09K11/06H01L51/0037H01L51/0039C08G61/126C09K2211/1483H01L51/0043H01L2251/308C08G2261/3241C08G2261/1424Y02E10/549Y02P70/50H10K85/115H10K85/151H10K85/1135H10K2102/103
Inventor 周明杰黄杰黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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