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A kind of preparation method and application of double-cable polymer

A polymer, dual-cable technology, applied in the fields of semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve the problem of low photoelectric energy conversion efficiency, achieve simple and effective synthesis methods, improve stability, and high absorption range Effect

Active Publication Date: 2021-02-05
INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the photoelectric energy conversion efficiency of single-component polymer solar cells is relatively low, and most of them do not exceed 3%.

Method used

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  • A kind of preparation method and application of double-cable polymer
  • A kind of preparation method and application of double-cable polymer
  • A kind of preparation method and application of double-cable polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of benzodithiophenedione-benzodithiophene type double cable polymer PBDBPBI:

[0048] The synthetic reaction formula of double-cable polymer PBDBPBI is as follows image 3 shown.

[0049] Concrete synthetic steps are:

[0050] (1) In a 100mL reaction flask, dissolve dialkyl bromide-substituted benzodithiophene M1-1 (225mg, 0.22mmol), PBI-1 (350mg, 0.49mmol) into 30mL DMF, and add Potassium carbonate (93 mg, 0.67 mmol). Heat to 75 degrees Celsius, react for 24 hours, after cooling, add 100 mL each of chloroform and deionized water. The liquid was separated, the organic phase was washed with brine, dried and rotary evaporated to obtain the crude product. The crude product was separated through a silica gel column, eluent dichloromethane:petroleum ether=4:1 (V / V), to obtain pure M2-1 with a yield of about 50%. 1 H NMR (400MHz, CDCl3): δ (ppm) 8.60 (m, 8H), 8.53 (m, 8H), 7.52 (s, 2H), 7.16 (s, 2H), 6.87 (s, 2H), 5.18 (t ,2H),4.18(t,4H),2.89(t,4H),2.26(m,4H),...

Embodiment 2

[0055] Synthesis of benzodithiophenedione-benzodithiophene type double cable polymer PBDBPBI-Cl:

[0056] The synthetic reaction formula of double-cable polymer PBDBPBI-Cl is as follows Figure 4 shown.

[0057] Concrete synthetic steps are consistent with embodiment 1.

[0058] The only difference is that benzodithiophene M1-2 substituted with chlorinated dialkyl bromide is used as the starting material, and the obtained intermediate M2-2 1 H NMR picture as Figure 9 as shown, 13 C NMR picture as Figure 10 shown. PBDBPBI-Cl 1 H-NMR such as Figure 11 shown.

[0059] The ultraviolet-visible absorption spectrum (UV-vis) of PBDBPBI-Cl is as Figure 13 Shown; The J-V curve of the single-component organic solar cell device of PBDBPBI-Cl is as Figure 14 Shown; The external quantum efficiency (EQE) of the single-component organic solar cell device of PBDBPBI-Cl is as Figure 15 shown.

Embodiment 3

[0061] Synthesis of benzodithiophenedione-benzodithiophene double cable polymer PBDBNDI:

[0062] The synthetic reaction formula of double-cable polymer PBDBNDI is as follows Figure 5 shown.

[0063] Concrete synthetic steps are:

[0064] (1) In a 100mL reaction flask, dissolve the dialkyl bromide-substituted benzodithiophene M1-1 (98mg, 0.091mmol), NDI-1 (124.5mg, 0.23mmol) in 15mL DMF, and wait for the dissolution equilibrium Potassium carbonate (38 mg, 0.28 mmol) was added.

[0065] Heat to 75 degrees Celsius, react for 12 hours, and suction filter while hot, wash the obtained solid several times with hot water, and then wash 50 mL with hot ethanol. After vacuum drying, pure M2-3 was obtained with a yield of about 87%. 1 H NMR (400MHz, CDCl 3 ): δ(ppm)8.74(s,8H),7.53(s,2H),7.14(s,2H),4.20(d,4H),4.11(d,4H),2.87(t,4H),1.98( s,2H),1.30(m,92H),0.84(m,12H).M2-3 1 H NMR as Figure 12 shown.

[0066] (2) M2-3 (39.27 mg, 19.6 μmol), M3-1 (18.30 mg, 19.6 μmol) were dissolv...

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Abstract

A preparation method and application of a double-cable polymer. The double-cable polymer is a benzodithiophenedione-benzodithiophene type double-cable polymer. The structural formula of the double-cable polymer is shown in the attached drawing of the abstract. The preparation method of the double-cable polymer comprises the following steps: (1) adding dialkyl bromide-substituted benzodithiophene and an acceptor nucleophile into an organic solvent, and adding potassium carbonate after the dissolution is balanced; Add chloroform and deionized water; liquid separation, washing, drying, and rotary evaporation to obtain the crude product; (2) Add the crude product and benzodithiophenedione bistin reagent to toluene and N,N-di In methylformamide, after the solution is degassed, add a palladium catalyst and triphenylphosphine; after the reaction, the product is precipitated with methanol and filtered; the filter cake is extracted with a solution, filtered through a filter membrane, and vacuum-dried to obtain a black polymer product. The double-cable polymer of the present invention has excellent photoelectric properties, and can be used as an organic semiconductor material and applied to single-component organic solar cell materials and the like.

Description

technical field [0001] The invention relates to a preparation method and application of a double-cable polymer, in particular to a preparation method and application of a double-cable conjugated polymer containing benzodithiophenedione-benzodithiophene, belonging to the technical field of organic semiconductor materials . Background technique [0002] Organic solar cells have become a research hotspot in recent years due to their potential application prospects due to their light weight, flexibility, adjustable structure, and solution processability. Among them, the research of two-component or multi-component bulk heterojunction solar cells is the most in-depth, and its energy conversion efficiency has exceeded 14%. However, this type of device has the disadvantages of many optimization steps and poor stability, which is not conducive to large-scale preparation. . In single-component solar cells, electron donors and acceptors are connected by covalent bonds to form a sing...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/12C08G61/126C08G2261/3241C08G2261/3243C08G2261/124C08G2261/91C08G2261/512H10K85/113Y02E10/549
Inventor 李韦伟游胜勇赵朝委晏南富
Owner INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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