Fullerene derivative, organic solar cell using same, and preparation method therefor

Patent metadata

Field	Value
Publication number	US-10270038-B2
Application number	US-201515112056-A
Country	US
Kind code	B2
Filing date	Feb 5, 2015
Priority date	Feb 5, 2014
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

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

First claim

The invention claimed is:

1. A fullerene derivative represented by the following Formula 1:

wherein:
Cn is a C 60 to C 84 fullerene;
p is an integer of 1 to 4, and
when p is 2 or more, the structures in the parenthesis are the same as or different from each other;
L is CRaRb, and
m is an integer of 0 to 3, and
when m is 2 or more, Ls are the same as or different from each other;
X1 to X3 are the same as or different from each other, and are each independently S, O, PR, CRR′, SO 2 , P(═O)R, or SiRR′,
at least one of X1 to X3 is S, O, PR, SO 2 , P(═O)R, or SiRR′; and
R1, R2, Ra, Rb, R and R are the same as or different from each other, and are 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, or a substituted or unsubstituted heterocyclic group, or
two substituents adjacent to each other in R1, R2, Ra, Rb, R and R′ combine with each other to form a double bond, cycloalkyl, cycloalkenyl, cyclic ketone, or an aromatic ring, or two substituents in the same atom in R1, R2, Ra, Rb, R and R′ combine with each other to form a spiro bond, a carbonyl group, an imine group, or an alkenyl group,
the formed cycloalkyl, cycloalkenyl, aromatic ring, or spiro bond is unsubstituted or substituted with an additional substituent,
when X1 and X3 are the same as or different from each other, and are each independently PR, CRR′, P(═O)R, or SiRR′, and m is 1, R1 or R2 and R or R′ of X1, and Ra or Rb and R or R′ of X3 do not form an aromatic ring simultaneously, and
when X2 is S, m is 1, R1 and R2 are hydrogen, or Ra and Rb are hydrogen, and two substituents adjacent to each other in R1, R2, Ra, Rb, R and R′ combine with each other to form an aromatic ring, the aromatic ring is substituted with an additional substituent.

2. The fullerene derivative of claim 1 , wherein R1, R2, Ra, Rb, R and R′ are the same as or different from each other, and are each independently hydrogen, a halogen group, an ester group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group, or
two substituents adjacent to each other in R1, R2, Ra, Rb, R and R′ combine with each other to form a double bond, or an aromatic ring, or
two substituents in the same atom in R1, R2, Ra, Rb, R and R′ combine with each other to form a Spiro bond, or a carbonyl group, and
the formed aromatic ring or spiro bond is unsubstituted or substituted with a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted arylamine group.

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

4. The fullerene derivative of claim 1 , wherein the structure in [ ] in Formula 1 is represented by any one of the following Formulae 2 to 10, 12 and 13:

wherein:
X1, X2, R1 and R2 are the same as those defined in Formula 1;
R11 to R16 are the same as or different from each other, and are 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, or a substituted or unsubstituted heterocyclic group, or
two substituents adjacent to each other in R11 to R16 combine with each other to form a double bond, cycloalkyl, cycloalkenyl, cyclic ketone, or an aromatic ring, or two substituents in the same atom in R11 to R16 combine with each other to form a spiro bond, a carbonyl group, an imine group, or an alkenyl group, and
the formed cycloalkyl, cycloalkenyl, cyclic ketone, aromatic ring, or spiro bond is unsubstituted or substituted with an additional substituent.

5. A fullerene derivative represented by the following Formula 1:

wherein:
Cn is a C 60 to C 84 fullerene;
p is an integer of 1 to 4, and
when p is 2 or more, the structures in the parenthesis are the same as or different from each other; and
the structure in [ ] in Formula 1 is represented by any one of the following Formulae:

wherein:
X is S, O or NR23;
R21 is hydrogen, a halogen group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted amine group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms; and
R22 and R23 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

6. A fullerene derivative represented by the following Formula 1:

wherein:
Cn is a C 60 to C 84 fullerene;
p is an integer of 1 to 4, and
when p is 2 or more, the structures in the parenthesis are the same as or different from each other; and
the structure in [ ] in Formula 1 is represented by any one of the following Formulae:

Assignees

• Lg Chemical Ltd

Inventors

• Bae Jaesoon
• Lee Jaechol
• Lee Jiyoung
• Jang Songrim
• Cho Keun
• Choi Doo Whan
• Bang Jiwon

Classifications

• C07D311/96

  spiro-condensed with carbocyclic rings or ring systems · CPC title

• C07D407/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title