Active layer, organic photovoltaic cell comprising the same and manufacturing method thereof

Patent metadata

Field	Value
Publication number	US-9299937-B2
Application number	US-201314039638-A
Country	US
Kind code	B2
Filing date	Sep 27, 2013
Priority date	Sep 28, 2012
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

The present specification provides a photoactive layer including an electron accepting material and an electron donating material, an organic photovoltaic cell including the same, and a method of manufacturing the organic photovoltaic cell, which includes treating the electron accepting material and the electron donating material by a non-solvent.

First claim

The invention claimed is:

1. An organic photovoltaic cell comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer provided between the first electrode and the second electrode and including a photoactive layer,
wherein the photoactive layer includes an electron accepting material and an electron donating material, and the electron accepting material and the electron donating material are treated by a non-solvent and
the electron donating material includes a polymer comprising:
an A unit represented any one of by the following formula 1, formula 2 and formula 3;
a B unit represented by the following formula 4; and
a C unit represented by the following formula 5:

wherein f and g are each an integer of 0 to 2,
wherein f and g are each an integer of 0 to 2,
R 2 to R 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; and a substituted or unsubstituted heterocyclic group including one or more of N, O and S atoms, or two adjacent substituent groups may bond together to form a condensation cycle,
X 1 and X 5 are the same as or different from each other, and each independently selected from the group consisting of CRR′, NR, O, SiRR′, PR, S, GeRR′, Se and Te,
Y 3 to Y 5 are the same as or different from each other, and each independently selected from the group consisting of CR, N, SiR, P and GeR,
R and R′ are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; and a substituted or unsubstituted heterocyclic group including one or more of N, O and S atoms, or two adjacent substituent groups may bond together to form a condensation cycle.

2. The organic photovoltaic cell of claim 1 , wherein the electron accepting material and the electron donating material are heat treated before, during, or after being treated by the non-solvent.

3. The organic photovoltaic cell of claim 2 , wherein a temperature of the heat treatment is a glass transition temperature (Tg) or more and a thermal decomposition temperature or less of the electron donating material.

4. The organic photovoltaic cell of claim 1 , wherein when the non-solvent is applied on the photoactive layer for 1 min to 60 min, a permeation distance of the non-solvent into the photoactive layer is 5% or more and less than 50% of a thickness of the photoactive layer.

5. The organic photovoltaic cell of claim 1 , wherein the non-solvent is one or two or more selected from the group consisting of water, alkanes, halohydrocarbons, ethers, ketones, esters, nitrogen compounds, sulfur compounds, acids, alcohols, phenols, and polyols.

6. The organic photovoltaic cell of claim 1 , wherein the electron accepting material is a fullerene derivative or a non-fullerene derivative.

7. The organic photovoltaic cell of claim 1 , wherein the non-solvent is a nitrogen compound non-solvent.

8. The organic photovoltaic cell of claim 1 , wherein the non-solvent is acetonitrile.

9. The organic photovoltaic cell of claim 1 , wherein the non-solvent is one or two or more selected from the group consisting of alkanes, ethers, alcohols, and acids.

10. The organic photovoltaic cell of claim 1 , wherein the non-solvent is methanol or 2-methoxyethanol.

11. The organic photovoltaic cell of claim 1 , wherein the electron accepting material is [6,6]-phenyl C-butyric acid methyl ester (PCBM), and the electron donating material is poly(3-hexylthiophene) (P3HT) or a polymer comprising a unit represented by the following formula 6:

wherein
x is a mole fraction and a real number in the range of 0<x<1;
y is a mole fraction and a real number in the range of 0<y<1;
x+y=1;
n is an integer ranging from 1 to 10,000;
R10 to R12 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

12. The organic photovoltaic cell of claim 1 , wherein a ratio (I c=c /I c−c ) of an antisymmetric value and a symmetric value of an absorption spectrum of FT-IR is increased by 110 to 150% as compared to an intrinsic value of the electron accepting material and the electron donating material.

13. The organic photovoltaic cell of claim 1 , wherein efficiency of the organic photovoltaic cell is increased by 110 to 200% as compared to the case where the photoactive layer includes the electron accepting material and the electron donating material before being treated by the non-solvent.

14. A photoactive layer comprising:
an electron accepting material, and
an electron donating material,
wherein the electron accepting material and the electron donating material are treated by a non-solvent and
the electron donating material includes a polymer comprising
an A unit represented any one of by the following formula 1, formula 2 and formula 3;
a B unit represented by the following formula 4; and
a C unit represented by the following formula 5:

wherein f and g are each an integer of 0 to 2,
R 2 to R 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group;

Assignees

• Lg Chemical Ltd

Inventors

• Lee Hangken
• Jeon Ji Hye
• Lee Jaechol
• Wang Dong Hwan
• Park Jong Hyeok
• Park O Ok

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• B82Y10/00 Primary

  Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/00

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title