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A-D-A type conjugated molecule based on dibenzo pentabasic fused heterocycle and preparation method of A-D-A type conjugated molecule

A technology of conjugated molecules, A-D-A, applied in electrical components, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve problems such as difficult energy levels, weak absorption, and difficult purification, and achieve simple operation, strong absorption capacity, and good spectrum The effect of absorption range

Inactive Publication Date: 2017-03-29
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the disadvantages of this type of material such as weak absorption in the visible light region, difficulty in regulating the energy level, and difficulty in purification [Energy Environ.Sci., 2011, 4, 1558], new polymers or small molecule acceptor materials were synthesized to replace this type of material appears to be particularly necessary

Method used

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  • A-D-A type conjugated molecule based on dibenzo pentabasic fused heterocycle and preparation method of A-D-A type conjugated molecule
  • A-D-A type conjugated molecule based on dibenzo pentabasic fused heterocycle and preparation method of A-D-A type conjugated molecule
  • A-D-A type conjugated molecule based on dibenzo pentabasic fused heterocycle and preparation method of A-D-A type conjugated molecule

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthetic route of embodiment 1. compound 3a is as follows:

[0033]

[0034] Under nitrogen protection, carbazole borate compound 1a (6.57g, 10mmol), compound 2 (5.4g, 24mmol), potassium carbonate (8.2g, 60mmol), 336 (1g), Pd (PPh 3) 4 (1.15g, 10% mol) was dissolved in 90mL toluene / water (5:1), heated to reflux for 72h, stopped the reaction, extracted with ether, combined organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, spin The solvent was dried and separated by column chromatography to obtain 3.8 g of yellow oily substance, the yield was 56%. 1 H NMR (500MHz, CDCl 3 )δ8.15–8.05(m,2H),7.76(s,1H),7.55(d,J=5.4Hz,3H),7.36(m,2H),7.28(d,J=5.4Hz,2H), 4.55(tt,J=10.0,5.2Hz,1H),3.72(s,6H),2.28(m,2H),1.93(m,2H),1.27–1.09(m,24H),0.81(t,J= 7.1Hz,6H). 13 C NMR (125MHz, CDCl 3 )δ164.01, 152.23, 142.11, 130.16, 124.03, 120.90, 113.27, 110.45, 56.74, 51.55, 33.78, 31.75, 29.41, 29.34, 29.19, 26.94, 22.58, 14.04.

Embodiment 2

[0035] Embodiment 2. The synthetic route of compound 4a is as follows:

[0036]

[0037] Under the protection of nitrogen, 23.4 mL of 2M butyllithium was added dropwise to a 250 mL three-neck flask containing 4-hexylbromobenzene (11.3 g, 46 mmol) and 100 mL of THF at -78 °C, and the reaction was kept at low temperature for 1 h. At this temperature, compound 3a (3.567 g, 7.8 mmol) was added dropwise to the reaction liquid, returned to room temperature and stirred overnight, hydrolyzed, extracted three times with ether, combined organic phases, washed with saturated brine, and dried over anhydrous magnesium sulfate. After suction filtration, the solvent was spin-dried and separated by column chromatography to obtain 3.9 g of a yellow-green oil, with a yield of 60%. 1 HNMR (500MHz, CDCl 3 )δ7.86(s,1H),7.82(s,1H),7.52(s,1H),7.38(s,1H),7.27(d,J=4.8Hz,2H),7.18(d,J=7.8 Hz,8H),7.02(d,J=7.4Hz,10H),4.64–4.49(m,1H),2.56–2.50(m,8H),2.36–2.24(m,2H),2.03–1.92(m, 2H),1.65–1.49(m,16H),1...

Embodiment 3

[0038] The synthetic route of embodiment 3. compound 5a is as follows:

[0039]

[0040] Add compound 4a (3.9g, 1.2mmol) in a 50mL single-necked round bottom flask, dry CH 2 Cl 2 150mL, boron trifluoride ether solution 15mL, heated to reflux overnight. Turn off heat. Cool, add water, CH 2 Cl 2 Extracted three times, combined the organic phases, washed with saturated brine, and dried over anhydrous magnesium sulfate. After suction filtration, the solvent was removed by spin, and 3.2 g of yellow solid was obtained by column chromatography, with a yield of 83%. 1 H NMR (500MHz, CDCl 3 )δ7.86(s,1H),7.83(s,1H),7.52(s,1H),7.38(s,1H),7.27(d,J=4.9Hz,2H),7.18(d,J=8.3 Hz,8H),7.06–7.00(m,10H),4.63–4.49(m,1H),2.57–2.48(m,8H),2.41–2.23(m,2H),2.00-1.94(,2H),1.62 –1.47(m,16H),1.39–1.09(m,41H),0.86(t,J=6.9Hz,12H),0.79(t,J=6.9Hz,6H). 13 C NMR (125MHz, CDCl 3 )δ156.39,144.98,143.08,143.04,141.08,135.11,134.66,128.20,127.93,127.18,123.36,102.15,99.54,62.20,56.81,35.59,33.81,31.78,3...

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Abstract

The invention belongs to the technical field of organic optoelectronic materials, and particularly relates to an A-D-A type conjugated molecule based on dibenzo pentabasic fused heterocycle and a preparation method and application of the A-D-A type conjugated molecule. The dibenzo pentabasic fused heterocycle is adopted as a core, pentabasic fused heterocycle is adopted as a bridge joint unit, and the tail end is connected with the A-D-A type conjugated molecule of an electron-deficient unit. The A-D-A type conjugated molecule based on the dibenzo pentabasic fused heterocycle and the preparation method and application of the A-D-A type conjugated molecule have the advantages that preparation is novel, operation is easy, and product separation and purification are easy. In addition, the A-D-A type conjugated molecule based on the dibenzo pentabasic fused heterocycle has good solubleness and stability, has a wide spectral absorption range and a proper level structure and is expected to be used as a donor or acceptor material of an organic solar cell.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic technology, and specifically relates to a class of A-D-A conjugated molecules based on a dibenzo five-membered aromatic heterocyclic condensed ring as a mother core, a five-membered aromatic heterocyclic ring as a bridging group, and an electron-deficient unit at the end. Its preparation method, and the application of this type of molecule as electron donor or electron acceptor material in the photoactive layer in the field of organic photovoltaic cells. Background technique [0002] Organic solar cells have the advantages of light weight, low cost, bendability, solution processing and large-area preparation, and have attracted the interest and attention of scientific researchers. Recently, polymer and small molecule solar cells have developed rapidly and made considerable progress [Adv. ; Nat.Commun., 2014, 5, 5293; Nature, 2014, 17, 1; J.Am.Chem.Soc. ,15027]. At present, the photoelectric ...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/14H01L51/54
CPCC07D495/04C07D495/14H10K85/626H10K85/657H10K85/6576Y02E10/549
Inventor 郭旺军高潮赵宝锋刘红利李继超张杰弥育华安忠维
Owner XIAN MODERN CHEM RES INST
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