Fluorene, anthracene and 2-thiophene thiazide-containing copolymer and preparation method and application thereof

A technology of dithiophene and copolymers, which is applied in the field of copolymers, can solve problems such as limiting the scope of application, and achieve the effects of improving solubility, improving utilization, and being easy to operate and control

Active Publication Date: 2012-05-09
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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  • Fluorene, anthracene and 2-thiophene thiazide-containing copolymer and preparation method and application thereof
  • Fluorene, anthracene and 2-thiophene thiazide-containing copolymer and preparation method and application thereof
  • Fluorene, anthracene and 2-thiophene thiazide-containing copolymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] This embodiment discloses polymers P1 and P2 with the following structures:

[0066]

[0067] The preparation steps of P1 and P2 are as follows:

[0068] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene:

[0069]

[0070] Set up an anhydrous and oxygen-free reaction device, constantly stirring and N 2 Under the protection of, add 9.0mmol of white 2,7-dibromo-9,9-dioctylfluorene to the three-necked bottle, inject 150ml of refined tetrahydrofuran solvent with a syringe, and then slowly inject it with a syringe at -78℃ 27.0 mmol n-BuLi, stirred and reacted for 2 hours. After 2 hours of reaction, 30.6mmol 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was injected with a syringe at -78℃, and the temperature was raised to React overnight at room temperature.

[0071] After the reaction, a saturated NaCl aqueous solution was added, extracted with chloroform, dried over anhydrous sodium sulfate, filtered, and the filtrate was collected ...

Embodiment 2

[0079] This embodiment discloses polymers P3 and P4 with the following structures:

[0080]

[0081] The preparation steps of P3 and P4 are as follows:

[0082] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dihexylfluorene:

[0083] The preparation process refers to step one in Example 1.

[0084] Step 3. Preparation of P3 and P4:

[0085]

[0086] Add 1 mmol, 9,10 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dihexylfluorene in the reactor -Dibromo-2,6-bis(2-octyldecyl)anthracene 0.8mmol (refer to Klaus Mullen et al. Macromol.Chem.Phys.2006,207,1107-1115 for the synthesis method of this compound), 5,5' -Dibromo-3,3'-di-n-octyl methylene silicon-2,2'-dithiophene 0.2mmol, palladium acetate (Pd(OAc) 2 )3mg, 2mol / L Na 2 CO 3 10ml of aqueous solution and 40ml of toluene solvent, through repeated N 2 And evacuated to make the reaction system in an anaerobic state, and react at 100°C for 24h.

[0087] After reacting for 24 hours, add deionized water and t...

Embodiment 3

[0091] This embodiment discloses polymers P5 and P6 with the following structures:

[0092]

[0093] The preparation steps of P5 and P6 are as follows:

[0094] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-bis(dodecyl)fluorene :

[0095] The preparation process refers to step one in Example 1.

[0096] Step 2. Preparation of P5 and P6:

[0097]

[0098] Add 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-bis(dodecyl)fluorene in the reactor 1mmol, 9,10-dibromo-2-fluoroanthracene 0.5mmol (see Elimelech Rochlin et al. J.Org.Chem., 2003, 68, 216-226 for the synthesis method of this compound), 5,5'-dibromo -3,3'-Diethylhexyl methylene silicon-2,2'-bithiophene 0.5mmol, tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 )0.02mmol, 2mol / L Na 2 CO 3 10ml of aqueous solution and 40ml of toluene solvent, through repeated N 2 And evacuated to make the reaction system in an anaerobic state, and reacted at 80℃ for 58h.

[0099] After reacting for 58 hours, add de...

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Abstract

The invention belongs to the field of an optoelectronic material, and discloses a fluorene, anthracene and 2-thiophene thiazide-containing copolymer shown in Formula (P). In the formula, n is an integer between 1 and 100, m is an integer between 1 and 20, x and y are positive real numbers, and the sum of x and y is 1; R1 and R2 are respectively hydrogen, fluorine, cyano, alkyl with a C1-C40 straight or branched chain, alkoxy with a C1-C40 straight or branched chain, aryl or heteroaryl; and R3 and R4 are hydrogen and C1-C20 alkyl. The invention also provides a preparation method and an application of the fluorene, anthracene and 2-thiophene thiazide-containing copolymer. The fluorene, anthracene and 2-thiophene thiazide-containing copolymer has a high carrier mobility rate, high light absorbance and broad scope of light absorption, the rate of utilization of sunlight can be increased, and the process of the preparation method is simple, the yield is high, and the operation and control can be facilitated.

Description

Technical field [0001] The present invention relates to a copolymer, and more specifically to a type of copolymer containing fluorene, anthracene and dithienosilole used in semiconductor materials. [0002] The invention also relates to a preparation method and application of a class of copolymers containing fluorene, anthracene and dithienosilole. Background technique [0003] High-efficiency solar cells usually use inorganic semiconductors as raw materials. However, the main silicon-crystalline solar cells currently on the market have complex production processes, serious pollution, high energy consumption, and high costs, which inhibit the development of their commercial applications. Therefore, the use of cheap materials to prepare low-cost, high-efficiency solar cells has always been a research hotspot and difficulty in the photovoltaic field. On the one hand, organic semiconductor materials have good environmental stability, low production cost, easy modulation of functions,...

Claims

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Application Information

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