Fullerene derivative, organic solar cell using same, and manufacturing method thereof

Patent metadata

Field	Value
Publication number	US-9923143-B2
Application number	US-201414778797-A
Country	US
Kind code	B2
Filing date	Apr 17, 2014
Priority date	Apr 17, 2013
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The present specification relates to a fullerene derivative, an organic solar cell including the same, and a fabricating method thereof.

First claim

The invention claimed is:

1. A fullerene derivative of any one of the following Chemical Formulae 2 to 5:

wherein:
m is an integer of 0 or 1;
p is an integer of 1 to 3;
when p is 2 or greater, the structures within the parenthesis are the same as or different from each other;
Cn is fullerene of C 60 to C 84 ;
R1, R2 and R5 to R10 are the same as or different from each other, and each independently hydrogen; deuterium a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxyl group; an ester group; a carbonyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl 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; or a substituted or unsubstituted heteroring group that includes one or more of N, O and S atoms; or
adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; a substituted or unsubstituted heteroring that includes one or more of N, O and S atoms, or substituents within the same carbon form a spiro bond; a carbonyl group; a substituted or unsubstituted imine group; or a substituted or unsubstituted alkenyl group;
X1 to X4 are the same as or different from each other, and each independently CRx; or N;
Y1 to Y4 are the same as or different from each other, and each independently CRy; or N;
X5 to X7 are the same as or different from each other, and each independently CRx′; S; or NRx′;
Y5 to Y7 are the same as or different from each other, and each independently Cry′, S; or NRy′; and
Rx, Ry, Rx′ and Ry′ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, an ester group, a carbonyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylalkyl 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, or a substituted or unsubstituted heteroring group that includes one or more of N, O and S atoms, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring, or a heteroring that includes one or more of N, O and S atoms, or a spiro bond;
when m is 0, at least one of the substituents of the ring formed by the adjacent substituents of R1, R2, R5 to R8 and R1, R2, R5 to R8, Rx, Ry, Rx′ and Ry′ is -(L)a-(M)b;
when m is 1, at least one of the substituents of the ring formed by the adjacent substituents of R1, R2, R5 to R10 and R1, R2, R5 to R10, Rx, Ry, Rx′ and Ry′ is -(L)a-(M)b;
a is an integer of 0 or 1;
bis an integer of 1 or 2;
L is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; a substituted or unsubstituted divalent ether group having 1 to 20 carbon atoms; a substituted or unsubstituted divalent aromatic hydrocarbon ring having 5 to 30 carbon atoms; or a divalent aromatic heteroring that includes one or more of N, O and S atoms;
M is

and
R is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, an ester group, a carbonyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkyloxy 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 silyloxy 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, a substituted or unsubstituted heteroaryl group that includes one or more of N, O and S atoms, or a substituted or unsubstituted heteroaryloxy group that includes one or more of N, O and S atoms.

2. The fullerene derivative of claim 1 , wherein m is 0.

3. The fullerene derivative of claim 1 , wherein m is 1.

4. The fullerene derivative of claim 1 , wherein at least one of the substituents of the hydrocarbon ring formed by the adjacent substituents of R1, R2, R5 to R10, and R1, R2, R5 to R8, Rx, Ry, Rx′ and Ry′ is -(L)a-(M)b.

5. The fullerene derivative of claim 1 , wherein a is an integer of 0 or 1; and
L is a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms; or a substituted or unsubstituted phenylene group.

6. The fullerene derivative of claim 1 , wherein R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 60 carbon atoms, a substituted or unsubstituted arylalkoxy group having 7 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, which includes one or more of N, O and S atoms, or a substituted or unsubstituted heteroaryloxy group having 2 to 60 carbon atoms, which includes one or more of N, O and S atoms.

7. The fullerene derivative of claim 1 , wherein R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkoxy group having 7 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubsti

Assignees

• Lg Chemical Ltd

Inventors

• Bae Jaesoon
• Lee Jaechol
• Lee Jiyoung
• Lee Hangken
• Jang Songrim
• Choi Jeong Min
• Kim Jinseck
• Cho Keun
• Choi Doo Whan

Classifications

• C01B32/156 Primary

  After-treatment · CPC title

• C07D277/36

  Sulfur atoms · CPC title

• C07C69/75

  of acids with a six-membered ring · CPC title

• C07D333/16

  by oxygen atoms · CPC title

• C07C2601/14

  The ring being saturated · CPC title