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Diketopyrrolopyrrole-benzothiadiazolyl conjugated derivative and its preparation method and application

A diketopyrrolopyrrole and benzothiadiazolyl technology, which is applied in the field of diketopyrrolopyrrole organic small molecule optoelectronic materials and its preparation, can solve the problems of less research, achieve fewer synthesis steps, and enhance π -π interaction, effect of improving hole transport performance

Active Publication Date: 2020-07-28
XUZHOU UNIV OF TECH
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  • Claims
  • Application Information

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Problems solved by technology

At present, this efficient and environmentally friendly direct arylation synthesis of DPP derivatives still has many synthetic challenges. In addition, the research on diketopyrrolopyrrole-benzothiadiazolyl conjugated derivatives in organic solar cells and organic field-effect transistors is relatively limited. few

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  • Diketopyrrolopyrrole-benzothiadiazolyl conjugated derivative and its preparation method and application

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Embodiment 1

[0029] This embodiment discloses the organic small molecule diketopyrrolopyrrole-benzothiadiazolyl conjugated derivative TBT (DPPT 2 ) 2 Concrete synthetic process, reaction formula is as follows:

[0030]

[0031] Add compound BrDPPT to a 25 mL Shrek tube 2 (0.178g, 22mmol), TBT (0.033g, 11mmol), anhydrous K 2 CO 3 (373mg, 0.27mmol), PivOH (29.2mg, 0.032mmol) and Pd(OAc) 2 (4.5 mg, 0.022 mmol). Stir in anhydrous state, add dimethylacetamide (DMA, 5 mL), and react at 110° C. for 10 hours under nitrogen protection. Stop the reaction, cool to room temperature, extract the organic phase with dichloromethane, wash with water, dry over anhydrous sodium sulfate, and filter. The organic phase was purified by column chromatography, the stationary phase was silica gel, and the eluent was petroleum ether / dichloromethane. After separation, washing with methanol and drying was obtained as a black solid (160 mg, 81%). 1 H NMR (400MHz,): δ (ppm) 8.82 (m, 4H), 8.06 (d, J = 2.8Hz, ...

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Abstract

The invention discloses a pyrrolopyrrole diketone-benzothiadiazolyl conjugated derivative and a preparation method and application thereof. The pyrrolopyrrole diketone-benzothiadiazolyl conjugated derivative has the general structure shown in the description. The preparation method comprises the following steps of: under the protection of nitrogen, putting 4,7-bis (thiophene-2-yl) benzo[c][1,2,5]thiadiazole and pyrrolopyrrole diketone bithiophene compounds into a reaction system catalyzed by palladium acetate, carrying out carbon-hydrogen activation direct coupling reaction, and separating and purifying the prepared crude product to obtain the pyrrolopyrrole diketone-benzthiadiazolyl conjugated derivative. According to the invention, the dithienyl pyrrolopyrrolopyrrolodione and the benzothiadiazolyl derivative are coupled, so that the prepared material has good visible near-infrared light absorption performance, and higher hole mobility, solubility and photoelectric conversion efficiency.

Description

technical field [0001] The invention relates to a diketopyrrolopyrrole organic small molecule optoelectronic material and a preparation method thereof. The diketopyrrolopyrrole-benzothiadiazolyl conjugated derivative can be applied to organic solar cells and organic thin film field effect transistors , belongs to the field of organic optoelectronic materials. Background technique [0002] Solution-processed organic semiconductors have the advantages of simple preparation process, low cost, flexible devices and large-area production, and have attracted extensive attention in recent years. Among them, organic small molecule materials have the advantages of fixed structure and small material batch difference, and have become a hot spot in the research of organic semiconductors. [0003] Diketopyrrolopyrrole (DPP) is a commonly used dye, and the DPP core has good planarity and strong intermolecular interactions, including hydrogen bonding and π–π interactions, to facilitate cha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C07D487/04H01L51/30
Inventor 王士凡堵锡华董黎明王晓辉么冰臧运晓
Owner XUZHOU UNIV OF TECH
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