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Conjugated polymer semiconductor materials based on thienoarylindole unit and preparation method thereof, and application of conjugated polymer semiconductor materials in high-efficiency polymer solar cells.

A technology of conjugated polymers and semiconductors, which is applied in the manufacture of semiconductor/solid-state devices, semiconductor devices, circuits, etc., can solve the problems of application research in the ascendant, and achieve the effects of good solubility, convenient purification, and simple preparation

Active Publication Date: 2015-12-23
NANJING UNIV OF POSTS & TELECOMM
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  • Description
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Problems solved by technology

At the same time, the source of organic conjugated polymer materials is rich and varied, and the structure of polymer materials can be optimized to facilitate the regulation of their physical properties and film-forming characteristics. Conjugated polymer optoelectronic materials are used in organic light-emitting Applied research in the fields of diodes, field effect transistors, solar cells, biological and chemical sensing is in the ascendant

Method used

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  • Conjugated polymer semiconductor materials based on thienoarylindole unit and preparation method thereof, and application of conjugated polymer semiconductor materials in high-efficiency polymer solar cells.
  • Conjugated polymer semiconductor materials based on thienoarylindole unit and preparation method thereof, and application of conjugated polymer semiconductor materials in high-efficiency polymer solar cells.
  • Conjugated polymer semiconductor materials based on thienoarylindole unit and preparation method thereof, and application of conjugated polymer semiconductor materials in high-efficiency polymer solar cells.

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of Polymer PTiDBT(I)

[0049] In a single-necked round bottom flask (250mL), add p-dibromobenzene (11.8g, 50mmol), dichloromethane (50mL), under ice-water bath, add nitric acid (10mL) and sulfuric acid (27.5mL) dropwise, at 0°C , stirred for 2 hours, then added water to quench the reaction, extracted with dichloromethane, washed the organic phase with water, saturated sodium bicarbonate, and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated, and recrystallized from ethanol to obtain 12.6g of 2-nitro - p-dibromobenzene, yield 90%.

[0050]

[0051] In a two-neck flask (100mL), dissolve 2-nitro-p-dibromobenzene (2.80g, 10mmol), 2-thiopheneboronic acid (1.53g, 12mmol) in 20mL of toluene, inject 15mL of 2M potassium carbonate solution. Gas three times, under the protection of nitrogen, add tetrakis(triphenylphosphine)palladium (150mg, 0.14mmol), heat to 75°C, react for 24 hours. Naturally cooled to room temperature, ex...

Embodiment 2

[0065] Preparation of Polymer PTiDDTBT(II)

[0066] In a single-necked round-bottomed flask (250mL), add p-dibromobenzene (12.0g, 50mmol), dichloromethane (50mL), add nitric acid (10mL) and sulfuric acid (25mL) dropwise under an ice-water bath, and at 0°C, Stir the reaction for 2 hours, then quench the reaction with water, extract with dichloromethane, wash the organic phase with water, saturated sodium bicarbonate, and saturated sodium chloride solution, dry over anhydrous magnesium sulfate, concentrate, and recrystallize from ethanol to obtain 12.5 g of 2-nitro- For p-dibromobenzene, the yield is 90%.

[0067]

[0068] In a two-neck flask (100mL), dissolve 2-nitro-p-dibromobenzene (2.80g, 10mmol), 2-thiopheneboronic acid (1.42g, 11mmol) in 30mL of toluene, inject 20mL of 2M potassium carbonate solution. Gas three times, under the protection of nitrogen, add tetrakis(triphenylphosphine)palladium (150mg, 0.14mmol), heat to 90°C, react for 24 hours. Naturally cooled to roo...

Embodiment 3

[0082] Preparation of Polymer PTiDTBT(II)

[0083] In a two-neck flask (150mL), dissolve the alkylated thienoindole (4.62g, 10mmol), 2-thiophene boronic acid (1.42g, 11mmol) in 50mL of toluene, inject 30mL of 2M potassium carbonate solution. Three times, under nitrogen protection, tetrakis(triphenylphosphine)palladium (150mg, 0.14mmol) was added, heated to 90°C, and reacted for 24 hours. Naturally cooled to room temperature, extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain 3.75 g of a colorless liquid with a yield of 78%.

[0084] 1 HNMR (400MHz, CDCl 3 )δ (ppm) 7.73 (d, J = 8.2Hz, 1H), 7.59 (d, J = 1.2Hz, 1H), 7.45 (dd, J = 8.2, 1.5Hz, 1H), 7.40–7.33 (m, 2H ),7.28(d,J=1.1Hz,1H),7.11(dd,J=5.1,3.5Hz,1H),7.04(d,J=5.2Hz,1H),4.14(d,J=7.3Hz,2H ),2.39-1.95(m,1H),1.43-1.19(m,24H),0.86(m,6H). 13 CNMR (100MHz, CDCl 3 )δ(ppm)146.57,146.03,142.08,128.84,128.00,126.92,124.03,122.43,121.25,119.19,117.76,115.95,110.68,107.37,49.67,3...

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Abstract

The invention discloses conjugated polymer semiconductor materials based on thienoarylindole unit and a preparation method thereof, and application of the conjugated polymer semiconductor materials in high-efficiency polymer solar cells. The structure is disclosed as general formula (I), wherein Ar represents aryl group, substituted aryl group, heterocyclic aryl group or substituted heterocyclic aryl group; R can be a straight-chain alkyl group or branched alkyl group; E represents carbon atom, nitrogen atom, silicon atom or the like; and A represents an electron-deficient receptor unit, and is generally an electron-deficient conjugated aryl group. The semiconductor materials disclosed by the invention have the advantages of favorable solubility, favorable heat stability, favorable film formation property, higher migration rate and high polymer solar cell photoelectric conversion efficiency (up to 5.83%). The thienoarylindole unit and derivative materials thereof obtained by the preparation method are hopeful to be widely used in the fields of organic solar cells, organic field-effect transistors and other photoelectric semiconductor devices.

Description

technical field [0001] The invention relates to the design and synthesis of a class of organic conjugated semiconductor materials and their application in polymer solar cell devices, in particular to a class of conjugated polymer semiconductor materials based on thienoarylindole units, their preparation and their high-efficiency Applications of polymer solar cells. Background technique [0002] As a new type of functional material, organic conjugated polymers have been gradually recognized for their rich functional properties. From small molecules to macromolecules, their properties such as electromagnetic light become more and more obvious. As early as the 1970s, organic conjugated polymer materials have attracted widespread attention. As a new type of functional material, they not only have the electronic properties of metals and semiconductors, but also have some advantages of polymers, such as light weight and low price. These advantages make it a potential application...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 赵保敏黄维李劝黄红艳张信珍傅妮娜
Owner NANJING UNIV OF POSTS & TELECOMM
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