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Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole chromophores for small molecule or vapor processed solar cells

a technology of pyrrolopyrrole and chromophores, which is applied in the direction of semiconductor devices, electrical devices, nanotechnology, etc., can solve the problems of difficult to synthesize “good” p3ht, large amount of sunlight wasted in this system, and high molecular weight and high regioregularity

Inactive Publication Date: 2010-12-30
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about an optoelectronic device that uses a mixture of a non-polymeric electron donor material and an electron acceptor material. The device includes a first hole-collecting electrode, an optional hole-transporting layer, a layer comprising a mixture of an electron donor material and an electron acceptor material, and a second electron-collecting electrode. The invention also includes a method of fabricating the device using solution processing. The non-polymeric electron donor materials include compounds of the diketopyrrolopyrrole structure. The invention also includes a photovoltaic device that uses a mixture of a non-polymeric electron donor material and an electron acceptor material. The non-polymeric electron donor materials can be selected from a variety of groups, such as thiophene, bithiophene, terthiophene, and benzothiophene. The invention also includes a method of fabricating the photovoltaic device using solution processing. The optoelectronic device can be used for various applications, such as photovoltaic devices.

Problems solved by technology

Although this system is capable of yielding some of the highest reported efficiencies among organic photovoltaics, it suffers from two significant shortcomings: i) the P3HT-PCBM mixture does not absorb light with wavelengths longer than about 650 nm, and thus a large fraction of sunlight is wasted in this system; and ii) the P3HT must have a relatively high molecular weight and very high regioregularity.
Synthesizing “good” P3HT can be problematic as the consistency between different batches of P3HT can vary.
Although such materials are successfully able to absorb a large fraction of the solar spectrum, most of them do not yield efficient BHJ photovoltaics due to inadequate electrical properties such as low charge carrier mobilities, incorrectly aligned HOMO and LUMO levels, or poor solid state morphologies.
However, the material is polymeric and there have been problems reproducing results using PCPDTBT from different sources.
Efficiencies as high as 6.5% have been reported using this type of system; however, fabricating two photovoltaic layers on top of each other adds a significant amount of complexity to the device architecture and difficulty in processing.
Fourth, the efficiencies observed in photovoltaics fabricated using this system are higher than those previously reported for solution-processed, non-polymeric photovoltaics.

Method used

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  • Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole  chromophores for  small molecule  or vapor processed solar cells
  • Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole  chromophores for  small molecule  or vapor processed solar cells
  • Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole  chromophores for  small molecule  or vapor processed solar cells

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Compound 4

[0167]Compound 4 was synthesized according to the following synthetic procedure:

[0168]Part A. The parent 2,5-dihydro-1,4-dioxo-3,6-dithienylpyrrolo[3,4-c]-pyrrole (1) was prepared in 55% yield following a previously reported procedure which comprises the reaction of 2-thiophenecarbonitrile with 0.5 eq of di-n-butyl succinate ester and an excess of potassium t-butoxide using 2-methyl-2-butanol as solvent. See Tamayo et al., J. Phys. Chem. C 112:15543 (2008) and references therein.

[0169]Part B. Compound (2) was synthesized according to a modified literature procedure. Zambounis et al. Nature 1997, 388, 131. In a three-necked, oven-dried 100 mL round bottom flask, 1 (3.0 g, 10.0 mmol) was dissolved in 150 mL of anhydrous tetrahydrofuran (THF) and the resulting solution was purged with argon for ten minutes. Dimethylaminopyridine (DMAP 3.0 g, 25 mmol) was added and the reaction mixture was stirred for 15 minutes under argon at room temperature. Di-tert-butyl-dicar...

example 2

Device Fabrication

[0175]Indium tin oxide (ITO)-coated glass substrates (Thin Film Devices) were cleaned with detergent and de-ionized water after which the substrates were sonicated for 10 minutes in soap solution, de-ionized water, acetone and isopropanol. The ITO substrates were then treated in a UV ozone cleaner for 30 minutes followed by spin coating a solution of poly(3,4-ethylene dioxythiophene:poly(styrenesulfonate) (PEDOT:PSS, Baytron P) (5000 rpm for 40 seconds). The PEDOT:PSS film was dried at 140° C. inside a glovebox for 15 minutes which yielded a film 60 nm thick. A 2% (w / v) blend solution of compound (4) and PCBM (Nano-C, USA) in chloroform (CHCl3) was filtered through a 0.45 μm poly(tetrafluoroethylene) (PTFE) filter and spin coated at 1500 rpm for 60 seconds on top of the PEDOT:PSS layer. Subsequently, aluminum (1200 Å) was thermally evaporated at a pressure of 1×10−7 Torr at room temperature using a shadow mask. Illumination was done through the glass slide using li...

example 3

Electrochemical and Photophysical Characterization of (4)

[0176]Cyclic voltammetry (CV) was performed using an EG&G potentiostat / galvanostat model 283. Anhydrous dichloromethane was used as the solvent under an inert atmosphere, and 0.1 M solution tetra-butyl ammonium hexafluorophosphate was used as the supporting electrolyte. A glassy carbon rod was used as the working electrode, a platinum wire was used as the counter electrode, and a silver wire was used as a pseudo reference electrode. The redox potentials are obtained by taking the average of anodic and cathodic waves and are reported relative to a ferrocenium / ferrocene (Cp2Fe+ / Cp2Fe, 0.475 V versus SCE in dichloromethane) redox couple used as an internal reference. UV-visible absorption spectra were recorded on a Shimadzu UV-2401 PC dual beam spectrometer. Steady-state fluorescence experiments at room temperature were performed using a PT1 (Lawrenceville, N.J.) Quantum Master fluorimeter equipped with a Xenon lamp excitation so...

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Abstract

Optoelectronic devices, such as photovoltaic devices, comprising a low band gap, solution processable diketopyrrolopyrrole or dithioketopyrrolopyrrole chromophore core or cores are disclosed. Also disclosed are methods of fabricating such optoelectronic devices.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority benefit of U.S. Provisional Patent Application No. 61 / 163,789, filed Mar. 26, 2009. The entire content of that application is hereby incorporated by reference herein in its entirety.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT[0002]This invention was made with Government support under grants N000140510677 and N000140811226 awarded by the Office of Naval Research, and grant DE-FG02-06ER46324 awarded by the Department of Energy. The Government has certain rights in this invention.BACKGROUND OF THE INVENTION[0003]Solar cells based on organic semiconductors are evolving into a promising cost-effective alternative to silicon-based solar cells due to low-cost fabrication by solution-processing, ease of processing, light weight, and compatibility with flexible substrates. Gunes et al. Chem. Rev. 2007, 107, 1324; Roncali, J., Acc. Chem. Res. 2009, 42, 1719. Devices based on these materials were ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L31/04H10K99/00
CPCB82Y10/00H01L51/0046Y02E10/549H01L51/4253H01L51/0062H10K85/211H10K85/649H10K30/30H10K30/50H10K85/6572H10K85/113H10K85/215H10K85/615H10K85/655H10K85/657H10K85/1135H10K30/82C08G61/126
Inventor NGUYEN, THUC-QUYENTAMAYO, ARNOLD BERNARTEWALKER, BRIGHTKENT, TYLERKIM, CHUNKITANTIWIWAT, MANANYA
Owner RGT UNIV OF CALIFORNIA
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