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A class of small molecule compounds containing hepta-fused ring structure indacene a-d-a type and preparation method thereof

A small molecular compound, A-D-A technology, applied in organic chemistry, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problem that the photoelectric conversion efficiency is less than 10%, and achieve the effect of good charge transport performance and strong light absorption coefficient

Active Publication Date: 2021-07-27
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The charge-deficient unit of these materials is limited to the 5-position of the thiophene bridge unit, and the molecular skeleton is mostly a planar structure. Although this structure makes the absorption spectrum of some of these materials redshift to the near-infrared band, it is difficult to find the absorption spectrum. A well-matched single polymer donor material forms a spectral complementarity with it, and the photoelectric conversion efficiency of a two-component blended single-layer organic photovoltaic cell based on these small molecule acceptors is generally less than 10%.

Method used

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  • A class of small molecule compounds containing hepta-fused ring structure indacene a-d-a type and preparation method thereof
  • A class of small molecule compounds containing hepta-fused ring structure indacene a-d-a type and preparation method thereof
  • A class of small molecule compounds containing hepta-fused ring structure indacene a-d-a type and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Compound A1

[0021]

[0022] The synthetic route is as follows:

[0023]

[0024] (1) Synthesis of compound 3:

[0025] Add compound 1 672.5mg / 0.5mmol, 2-bromo-3-(2-ethylhexyloxy)thiophene-4-carbaldehyde 478mg / 1.5mmol, Pd(PPh 3 ) 4 40mg, toluene 30ml, heating under nitrogen protection, reflux for 24h, product extraction, washing, column chromatography (n-hexane: ethyl acetate = 100:1), to obtain 550mg of compound 3 (liquid phase content> 99%), the yield 73.5%. 1 H NMR (500MHz, CDCl 3 ),δ9.93(s,2H),7.94(s,2H),7.45(s,2H),7.18(d,8H),7.10(d,8H),6.88(s,2H),4.10(d, 4H),2.57(t,8H),1.76(m,2H),1.66-1.58(m,16H),1.50-1.26(m,32H),0.95-0.86(m,24H). 13 C NMR (125MHz, CDCl 3),δ181.09,164.32,157.11,153.37,146.23,142.93,141.91,139.04,137.06,135.16,129.62,128.45,127.68,126.39,122.71,119.30,117.72,111.12,74.46,63.07,39.43,35.52,31.65,31.28, 30.32, 29.07, 29.01, 23.78, 22.94, 22.55, 14.04, 14.02, 11.10. Anal. Calcd for (C 94 h 110 o 4 S 6 ): C 75.45, H 7.41, ...

Embodiment 2

[0032] Embodiment 2: Compound A2

[0033]

[0034] The synthetic route is as follows:

[0035]

[0036] Take 658mg / 0.44mmol of the above compound 3, 485mg / 2.5mmol of compound b, put it in a 100ml three-necked flask, dissolve it in 40ml of chloroform, then add 1.5ml of pyridine, heat and reflux for 6h, stop heating, cool, extract, wash, and wash with methanol After sedimentation and filtration, the resulting solid was purified by column chromatography and eluted with chloroform to obtain 582 mg of a blue-black solid with a yield of 69% and a liquid phase content of >99%. 1 H NMR (500MHz, CDCl 3 ),δ9.17(s,2H),8.66(d,2H),7.85(d,2H),7.72(m,4H),7.53(d,Hz,4H),7.19(d,8H),7.14( d,8H),6.93(s,2H),4.18(q,4H),2.63(t,8H),1.91(m,2H),1.62-1.55(m,16H),1.36-1.29(m,32H) ,0.96-0.86(m,24H). 13 C NMR (125MHz, CDCl 3 ),δ187.25,170.27,158.71,158.82,154.78,154.14,145.99,142.22,140.69,139.37,137.06,135.76,134.25,132.83,128.69,127.79,123.88,122.69,118.31,117.40,117.19,115.14,114.57,109.18, ...

Embodiment 3

[0037] Embodiment 3: the synthesis of compound A3

[0038]

[0039] The synthetic route is as follows:

[0040]

[0041] (1) Synthesis of Compound 5:

[0042] Add compound 1 672.5mg / 0.5mmol, 2-bromo-3-thiophenecarboxylic acid isooctyl-4-carbaldehyde 521mg / 1.5mmol, Pd(PPh 3 ) 4 40mg, toluene 30ml, heating under nitrogen protection, reflux for 24h, product extraction, washing, column chromatography (n-hexane: ethyl acetate = 100:1), to obtain 543mg of compound 5 (liquid phase content> 99%), the yield 70%. 1 HNMR (500MHz, CDCl 3 ),δ9.93(s,2H),7.94(s,2H),7.46(s,2H),7.19(d,8H),7.11(d,8H),6.89(s,2H),4.30(d, 4H),2.57(t,8H),1.81(m,2H),1.68-1.58(m,16H),1.50-1.26(m,32H),0.95-0.86(m,24H). 13 C NMR (125MHz, CDCl 3 ),δ181.10,165.29,160.10,157.11,153.39,146.23,142.93,141.92,139.04,137.06,135.16,129.62,128.45,127.68,126.39,122.71,119.30,117.72,111.12,74.46,63.07,39.43,35.52,31.65, 31.28, 30.32, 29.07, 29.01, 23.78, 22.94, 22.55, 14.04, 14.02, 11.10. Anal. Calcd for (C 96 h 1...

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Abstract

The invention discloses a class of indacene A-D-A type conjugated small molecular compounds containing a hepta-condensed ring structure, a preparation method thereof, and an application as a photoactive layer material in an organic photovoltaic device. This type of compound has the following general structure: it is based on the hepta-condensed ring as the electron-donating unit (D), with the thiophene ring as the bridging unit, and the 4-position of thiophene as the electron-withdrawing unit (A), using the A unit on the bridging thiophene Replace the difference in position, adjust the energy level structure and light absorption characteristics of the material, thereby adjusting the open circuit voltage, short circuit current and other parameters of the photovoltaic cell, and then improve the photoelectric conversion efficiency of the device.

Description

technical field [0001] The invention belongs to the field of organic photoelectric functional materials, and specifically relates to a class of indacene A-D-A type conjugated small molecule compounds containing a hepta-fused ring structure and a preparation method thereof, and this type of molecule as an n-type material in a photoactive layer in an organic compound. Applications in photovoltaic (OPV) devices. Background technique [0002] Among solar cells, organic solar cells have become one of the most active fields in photovoltaic research because of their light weight, low cost, simple preparation process, and the ability to be fabricated into flexible devices. The photoactive layer material is the key photosensitive layer of organic solar cells, and its properties determine the generation and diffusion of excitons, the separation and transport of charges, and ultimately determine the photoelectric conversion efficiency of the cell. [0003] The photoactive layer consis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C08K5/46C08L65/00H01L51/42H01L51/46
CPCC07D495/22C08K5/46C08L2203/204H10K85/615H10K85/655H10K85/6576H10K30/00C08L65/00Y02E10/549
Inventor 丛志远高潮王维平武海梅赵宝锋刘建群刘红利
Owner XIAN MODERN CHEM RES INST