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Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery

A technology of perylene tetracarboxylate and acceptor materials, applied in the field of organic optoelectronics, which can solve the problems of limited influence and adjustment ability, low battery open circuit voltage, weak absorption of fullerene derivatives, etc.

Inactive Publication Date: 2013-02-13
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the energy conversion efficiency of organic solar cells based on polymer and fullerene systems has reached about 9%, but this type of organic photovoltaic cells still faces many problems.
For example, fullerene derivatives, the change and modification of their chemical structure have limited influence and adjustment ability on their electronic structure. As n-type materials, their lower distribution of LUMO energy levels may lead to heterogeneity in the construction of energy levels with p-type materials. Junction, the excessive loss of absorbed solar energy in the process of photoinduced charge transfer may lead to low cell open circuit voltage
On the other hand, fullerene derivatives have weak absorption in the visible region, which is not conducive to the absorption of solar energy by heterojunctions.

Method used

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  • Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery
  • Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery
  • Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Poly-3,4,9,10-perylenetetracarboxylate-tetrakis(2-hexyldecyl)-alt-4,7-bis(thiophen-2-)yl[c]2,1,3-benzothiabis Preparation of azole (abbreviated as PPTTE-DTBT-a)

[0027] The synthetic route is as follows:

[0028]

[0029] (1) Preparation of 3,4,9,10-perylenetetracarboxylate-tetra(2-hexyldecyl) ester

[0030] Add 3.92g of PTCDA (10mmol) to a 250mL two-necked flask, then add 100mL of acetonitrile solution, 14.52g of 2-hexyldecanol (60mmol), 18.32g of 1-bromo-2-hexyldecane (60mmol) and 2.43g of DBU (80mmol), heated to reflux, monitored by TLC, and then cooled to room temperature. Washed with water, extracted with petroleum ether, and concentrated the organic phase. Distilled under reduced pressure to remove 2-hexyldecanol, and the crude product was subjected to silica gel column chromatography to obtain 9.93 g of pure compound (1), with a yield of 75%.

[0031] 1 H NMR (400MHz, CDCl 3 )δ[ppm]: 8.33(d, J=8.1Hz, 4H), 8.04(d, J=7.9Hz, 4H), 4.23(d, J=6.0Hz, 8H), 1.82...

Embodiment 2

[0042] Poly-3,4,9,10-perylenetetracarboxylate-tetrakis(2-ethylhexyl)-alt-4,7-di(thiophen-2-)yl[c]2,1,3-benzothiabis Preparation of azole (abbreviated as PPTTE-DTBT-b)

[0043] The synthetic route is as follows:

[0044]

[0045] The synthetic method of compound (4) in the synthetic route is the same as that of compound (1) in Example 1, with 2-ethylhexanol and 1-bromo-2-ethylhexane instead of 2-hexyldecanol and 1-bromo-2 - Hexyldecane. The synthesis of compound (5) is the same as that of compound (2) in Example 1.

[0046] (1) Poly-3,4,9,10-perylenetetracarboxylate-tetrakis(2-ethylhexyl)-alt-4,7-di(thiophen-2-)yl[c]2,1,3-benzene Preparation of thiadiazole

[0047] Under nitrogen protection, 0.517g 1,7-dibromo-3,4,9,10-perylenetetracarboxylate-tetrakis(2-ethylhexyl)ester (0.5mmol), 0.313g 4,7-bis( 2-trimethyltinyl-thiophen-5-)yl[c]2,1,3-benzothiadiazole (0.5mmol), 14.0mgPd 2 (dba) 3 and 27.4mg P(o-Tol) 3 Add it into a 50mL single-necked bottle, then add 20mL of anhyd...

Embodiment 3

[0050] Poly-3,4,9,10-perylenetetracarboxylate-tetrakis(2-octyl)-alt-4,7-bis(thiophen-2-)yl[c]2,1,3-benzothiadiazole Preparation (abbreviated as PPTTE-DTBT-c)

[0051] The synthetic route is as follows:

[0052]

[0053] The synthesis method of compound (6) in the synthetic route is the same as that of compound (1) in Example 1, with 1-octanol and 1-bromooctane instead of 2-hexyldecanol and 1-bromo-2-hexyldecane. The synthesis method of compound (7) is the same as that of compound (2) in Example 1. The synthetic method of polymer is the same as embodiment 2, replaces 1,7-dibromo-3,4 with 1,7-dibromo-3,4,9,10-perylenetetracarboxylic acid-tetra(2-octyl) ester, 9,10-Perylenetetracarboxylate-tetra(2-ethylhexyl) ester.

[0054] The polymer structure is characterized as follows: GPC: Mn=105.59K, Mw=311.187K, PDI=2.94, n=90. Elemental analysis C 70 h 80 N 2 o 8 S 3 Calculated for: C, 71.67; H, 6.82; N, 2.38; S, 8.19; Found: C, 70.16; H, 6.76; N, 2.35;

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Abstract

The invention discloses perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to a solar battery. The materials include a structure as refined in formula 1, in the formula 1, M is diazosulfide, dithienyl diazosulfide, selenole, dithienyl selenole, diselenium thiophene selenole, thiophene, dithiophene, terthienyl, benzene, selenophen, diselenide thiophene, terselenide thiophene, thiophene thiophthene, benzo dithiophene, benzo ditellurium thiophene, benzo ditellurium thiophene, or one of derivatives made on the basis of the compounds. R is a linear chain with more than four carbon atoms, a branched chain or an alkyl chain containing different heteroatoms. N is a natural number of 1-1000. By introducing comonomer M on the perylene ring skeletons 1, 7 positions, the level structure of polymer materials can be adjusted, and at the same time, optical property is improved, and use ratio of the materials to light is enhanced. By introducing R, dissolubility of the polymer materials can be adjusted, and utilization of a solution processing technology with low cost is facilitated. The materials can be applied to the field of organic optoelectronics.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a photoelectric functional polymer semiconductor acceptor material with adjustable energy band structure based on perylene tetracarboxylate derivatives, and also relates to its application in organic solar cells. Background technique [0002] Organic semiconductor materials have aroused extensive interest of researchers because of their excellent photoelectric properties. In the past two decades, organic electronics, which takes organic semiconductor materials and devices as research objects, has developed rapidly. Compared with other types of semiconductor materials, organic semiconductor materials can adjust their energy level structure and the range and intensity of sunlight absorption through chemical structure modification, and their solubility in different solvents can also be adjusted accordingly. Organic semiconductor materials have solution pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C08G61/10H01L51/46
CPCY02E10/549
Inventor 肖生强蒋友宇詹春蒋尊龙夏飞程金波吴迪
Owner WUHAN UNIV OF TECH
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