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Organic photovoltaic devices comprising fullerenes and derivatives thereof

A fullerene derivative, fullerene technology, applied in photovoltaic power generation, electrical solid-state devices, semiconductor devices, etc., to achieve good photovoltaic efficiency

Active Publication Date: 2009-09-09
SOLVAY USA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is driven in part by current high fuel prices and erratic fuel supplies

Method used

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  • Organic photovoltaic devices comprising fullerenes and derivatives thereof
  • Organic photovoltaic devices comprising fullerenes and derivatives thereof
  • Organic photovoltaic devices comprising fullerenes and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0195] Embodiment 1. A photovoltaic device, which includes:

[0196] The first electrode,

[0197] Second electrode,

[0198] At least one active layer deposited between the first and second electrodes, wherein the active layer includes at least one polythiophene and at least one fullerene derivative containing an electron withdrawing group.

[0199] 2. The device of embodiment 1, wherein the fullerene derivative is a C60 fullerene.

[0200] 3. The device according to embodiment 1, wherein the fullerene derivative is C70 fullerene.

[0201] 4. The device of embodiment 1, wherein the fullerene derivative is C 84 fullerene.

[0202] 5. The device of embodiment 1, wherein the fullerene derivative comprises C60Cl6, C60 (C9H8), C60Br24, C60Cl (CH2ClChC 12).

[0203] 6. The device of embodiment 1, wherein the polythiophene is a stereoregular polythiophene.

[0204] 7. The device of embodiment 1, wherein the polythiophene is a copolymer.

[0205] 8. The device of embodiment 1, further co...

Embodiment 1

[0234] Example 1: C 60 -Synthesis of indene adducts

[0235] As a starting point, use C 60 The indene adduct was synthesized by using the description in the reference (Puplovskis et al., "New Route for [60] Fullerene Functionalization in [4+2] Cycloaddition Reaction Using Idene." Tetrahedron Lett. 1997, 38, 285-288) . Will C 60 To about 6mg mL -1 The concentration is dissolved in o-dichlorobenzene. Indene relative to C 60 It was added in a 12-fold molar excess, and the resulting mixture was refluxed overnight. Most of the solvent evaporates under reduced pressure, and precipitation occurs after the addition of ethanol. The obtained solid was dried, dissolved in toluene, and then used with a Cosmosil Buckyprep analytical column (250 × 4.6 mm, Nacalai Tesque, Inc.) installed on an Agilent 1100 series instrument equipped with a variable wavelength detector operating at 330 nm. ) High pressure liquid chromatography analysis. 1ml min -1 The flow rate of toluene is used for elution....

Embodiment 2

[0236] Example 2: C 70 -Synthesis of Indene Monoadducts

[0237] The C70-indene monoadduct was synthesized according to the method developed for the C60-indene adduct. Will C 70 Dissolved in o-dichlorobenzene. After adding indene in a 12-fold molar excess, reflux was maintained for 8 hours. After reducing the volume under reduced pressure and adding ethanol, the solid was recovered, dried and redissolved in toluene. HPLC analysis using the same steps as above showed that there are mainly monoadducts, which may be due to the difference with C 60 -Compared with the synthesis of adducts, the reaction time is reduced. Purification using flash chromatography makes C 70 -The monoadducts are separated with a purity of 98.6%. The corresponding HPLC chromatogram is given below. Identified means C 70 Two main isomers with different addition sites on the cage.

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Abstract

The present invention provides photovoltaic cells comprising an active layer comprising, as p-type material, conjugated polymers such as polythiophene and regioregular polythiophene, and as n-type material at least one fullerene derivative. The fullerene derivative can be C60, C70, or C84. The fullerene also can be functionalized with indene groups. Improved efficiency can be achieved.

Description

[0001] Cross-references to related applications [0002] This application claims priority to the U.S. Provisional Application Serial No. 60 / 812,961 filed by Laird et al. on June 13, 2006, which is incorporated herein by reference in its entirety. Background technique [0003] There is a need to provide better materials and methods for organic photovoltaic (OPV) devices. This is partly driven by the current high fuel prices and unstable fuel supply. OPV devices can provide improvements over older silicon devices. See, for example, Perlin, John, "The Silicon Solar Cell Turns 50" NREL 2004; see also Dennler et al., "Flexible Conjugated Polymer-Based Plastic Solar Cells: From Basics to Applications," Procee dings of the IEEE, Vol. 93, No. 8 Period, August 2005, 1429-1439. Global climate change is also a contributing factor. Although it is known that conductive polymers or conjugated polymers (including, for example, polythiophene) can be combined with C60 fullerenes to provide active...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/42H10K99/00
CPCH01L51/0047B82Y99/00Y10S977/784H01L51/4253Y10S977/735H01L51/0036B82Y10/00Y10S977/778Y10S977/948Y10S977/737Y02E10/50Y10S977/738Y10S977/734Y02E10/549Y02E10/542Y02P70/50H10K85/113H10K85/215H10K30/30H10K30/50H10K85/211H01G9/2004H01L31/0256H01L2031/0344
Inventor W·达林·莱尔德瑞扎·史泰格马特亨宁·瑞查特维克托·维金斯拉里·斯科特托马斯·A·拉达
Owner SOLVAY USA
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