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A class of d(π-a) based pyrazindole terminal receptors 2 Small molecule donor material and preparation method and application

A technology of small molecule donor, pyrazine indole, which is applied in semiconductor/solid-state device manufacturing, electrical solid-state devices, semiconductor devices, etc., and can solve problems such as poor stability, low efficiency, and narrow absorption spectrum

Active Publication Date: 2021-07-30
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, organic small molecule solar cell materials still have problems such as narrow absorption spectrum, low carrier mobility, low efficiency and poor stability, so it is necessary to develop new high-performance small molecule donor materials

Method used

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  • A class of d(π-a) based pyrazindole terminal receptors <sub>2</sub> Small molecule donor material and preparation method and application
  • A class of d(π-a) based pyrazindole terminal receptors <sub>2</sub> Small molecule donor material and preparation method and application
  • A class of d(π-a) based pyrazindole terminal receptors <sub>2</sub> Small molecule donor material and preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] D(π-A) 2 Synthesis of small molecule donor material intermediates and target molecules (M1, M2, M3, M4, M5, IDP-2CN, IDQ-2F, IDQ-2Cl, TTIDP-2CN, TTIDP-2F and TTIDP-2Cl) Synthetic, its synthetic route is as follows:

[0064]

[0065] 1.1 Synthesis of 3,6-bis(octylthio)-thieno[3,2-b]thiophene (M1):

[0066]

[0067] Add 3,6-dibromothiophene[3,2-b]thiophene (5.0g, 16.9mmol) in a 200mL single-necked bottle, n-C 8 h 17 SH(1-octylthiol) (5.4g, 36.9mmol), DIEA (4.8g, 36.9mmol), DPPF (370mg, 0.7mmol), Pd 2 (dba) 3 (310mg, 0.3mmol), add 80mL toluene, vacuumize three times, under the protection of nitrogen, reflux and stir at 110°C for 24h, after the reaction is completed, the reactant is cooled to room temperature, the mixture is poured into water, extracted with dichloromethane (3 ×50mL), washed three times with water, dried with anhydrous magnesium sulfate, filtered, and the organic solvent was removed under reduced pressure, and the product was separated by column ...

Embodiment 2

[0089] Example 2 Synthesis of Small Molecule Donor TTIDP-4CN

[0090]

[0091] In a 100mL two-necked flask, sequentially add compound M4 (0.2g, 0.218mmol), compound IDP-4CN (0.189g, 0.479mmol), three (dibenzylideneacetone) dipalladium (5.98mg), three (o-tolyl ) phosphorus (7.94mg), toluene 10mL, under the condition of nitrogen protection, stirred and refluxed in an oil bath at 110°C for 24h. Stop the reaction, cool to room temperature, pour the reaction solution into 40mL water, extract with dichloromethane (3×25mL), dry over anhydrous magnesium sulfate, filter, spin off the organic solvent under reduced pressure, and pass the crude product through absolute ethanol / chloroform Recrystallization gave a red solid (282 mg, yield 84.9%). 1 H NMR (400MHz, CDCl 3 )δ8.46(d, J=2.2Hz, 1H), 7.97(dd, J=8.8, 2.1Hz, 1H), 7.44(d, J=9.0Hz, 1H), 7.32(s, 2H), 4.32( s,2H),2.89(s,2H),1.87(s,2H),1.66-1.14(m,30H),0.86(d, J=35.9Hz,7H).

Embodiment 3

[0092] Example 3 Synthesis of Small Molecule Donor TTIDQ-4F

[0093]

[0094] In a 100mL two-necked flask, sequentially add compound M4 (0.2g, 0.218mmol), compound IDQ-2F (0.214g, 0.479mmol), tris(dibenzylideneacetone) dipalladium (5.98mg), tris(o-tolyl ) Phosphorus (7.94mg), toluene 10mL, under the condition of nitrogen protection, stirred and refluxed in an oil bath at 110°C for 24h. Stop the reaction, cool to room temperature, pour the reaction solution into 40mL water, extract with dichloromethane (3×25 mL), dry over anhydrous magnesium sulfate, filter, spin off the organic solvent under reduced pressure, and pass the crude product through absolute ethanol / trichloro Recrystallization from methane gave a red solid (225 mg, 78.1% yield). 1 H NMR (400MHz, CDCl 3 ) δ8.68(s,1H),8.07-7.97(m,2H),7.85(d,J=19.4Hz,1H),7.51-7.45(m,2H),7.36 (d,J=3.9Hz,1H ),4.46(s,2H),2.98(t,J=7.3Hz,2H),1.95(s,2H),1.66(s,2H), 1.40(s,7H),1.25(s,21H),0.84 (d,J=20.9Hz,8H),0.07(s,14H).

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Abstract

The invention belongs to the field of organic small molecule solar cells, in particular to a class of D(π-A) based on pyrazine indole terminal electron acceptors 2 Small molecule donor materials and their preparation methods and applications. where D(π‑A) 2 The electron-donating (D) unit of the type small molecule is 3,6-bis-(octylthio)thienothiophene (TT), and the π bridge unit is alkylated, oxyalkylated or sulfur-alkylated thiophene or selenophene , the electron-withdrawing (A) unit is a new type of pyrazine indole derivatives, and this type of small molecule donor material is used in solution-processed small molecule solar cells. by PC 71 BM is the acceptor, and the energy conversion efficiency of the bulk heterojunction solar cell reaches 7.31%. The invention realizes the high-efficiency energy conversion of the small molecule donor material based on the terminal acceptor unit of the pyrazine indole derivative in the small molecule solar cell.

Description

technical field [0001] The invention belongs to the field of organic small molecule solar cells, in particular to a class of D(π-A) based on pyrazine indole terminal acceptors 2 Type small molecule donor material and preparation method, as well as the application of the material in the field of organic optoelectronic technology. Background technique [0002] Organic solar cells have become a research hotspot in the field of organic photovoltaics due to their advantages of low cost, light weight and large area preparation. As an organic small molecule donor material in the photosensitive active layer that absorbs sunlight and converts it into electrical energy, it has great market application prospects. [0003] However, organic small molecule solar cell materials still have problems such as narrow absorption spectrum, low carrier mobility, low efficiency and poor stability, so it is necessary to develop new high-performance small molecule donor materials. [0004] Since t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/6576H10K85/6572H10K30/30Y02E10/549
Inventor 刘煜刘座吉包成佳朱卫国崔苏倩
Owner CHANGZHOU UNIV
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