Copolymer and organic solar cell comprising same

Patent metadata

Field	Value
Publication number	US-9748489-B2
Application number	US-201414905242-A
Country	US
Kind code	B2
Filing date	Jun 19, 2014
Priority date	Jul 15, 2013
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

The present specification provides a copolymer and an organic solar cell including the same.

First claim

The invention claimed is:

1. A copolymer comprising:
a first unit of Formula 1; and
a second unit of Formula 2:

wherein in Formulae 1 and 2:
l is a real number, which is 0<l<1 as a mole fraction,
m is a real number, which is 0<m<1 as a mole fraction, and
l+m=1;
A and B are different from each other, and comprise one or more moieties selected from the group consisting of a direct bond; a monocyclic or polycyclic substituted or unsubstituted divalent heterocyclic group; a monocyclic or polycyclic substituted or unsubstituted divalent aromatic cyclic group; and a fused divalent ring in which a monocyclic or polycyclic heterocyclic group and a monocyclic or polycyclic aromatic cyclic group are substituted or unsubstituted;
R1, R4, R5 and R8 are the same as or different from each other, and are 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 hydroxyl 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; and a substituted or unsubstituted heterocyclic group; and
R2, R3, R6 and R7 are the same as or different from each other, and are 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 hydroxyl 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; and a substituted or unsubstituted aryl group.

2. The copolymer of claim 1 , wherein A and B are different from each other, and each is selected from any one of the following Formulae:

wherein:
X1 and X2 are the same as or different from each other, and each independently is selected from the group consisting of CRR′, NR, O, SiRR′, PR, S, GeRR′, Se, and Te, Y1 to Y4 are the same as or different from each other, and each independently is selected from the group consisting of CR, N, SiR, P, and GeR; and
R10 to R13 and R and R′ are the same as or different from each other, and each independently is selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxyl 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; and a substituted or unsubstituted heterocyclic group.

3. The copolymer of claim 1 , wherein a solubility of the second unit is larger than that of the first unit.

4. The copolymer of claim 1 , wherein a solubility of the second unit is 2 to 10 times larger than that of the first unit.

5. The copolymer of claim 1 , wherein a solubility of a copolymer comprising the first unit and the second unit in a solution selected from the group consisting of a chlorinated solvent, toluene, xylenes, trimethylbenzenes, and tetrahydrofuran is 1 mg/ml to 200 mg/ml at room temperature.

6. The copolymer of claim 1 , wherein a solubility of the copolymer comprising the first unit and the second unit in one or two or more solutions selected from the group consisting of chlorobenzene, toluene, xylene, and trimethylbenzene is 1 mg/ml to 200 mg/ml at room temperature.

7. The copolymer of claim 1 , wherein B comprises at least one substituent which increases a solubility at a side chain.

8. The copolymer of claim 1 , wherein B comprises at least one of a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted sulfide group having 1 to 40 carbon atoms, and a hydroxyl group at a side chain.

9. The copolymer of claim 1 , wherein the first unit of Formula 1 is any one of Formulae 1-1 to 1-3:

wherein in Formulae 1-1 to 1-3:
l is a real number, which is 0<l<1;
R1 and R4 are the same as or different from each other, and each independently is selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxyl 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; and a substituted or unsubstituted heterocyclic group;
R2 and R3 are the same as or different from each other, and each independently is selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxyl 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

Assignees

• Lg Chemical Ltd

Inventors

• Kim Jinseck
• Lee Jaechol
• Bae Jaesoon
• Lee Jiyoung
• Cho Keun
• Choi Doo Whan

Classifications

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• C08G2261/3246

  containing nitrogen and sulfur as heteroatoms · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C08G75/00

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title