Photoactive layer and organic solar cell comprising same

Patent metadata

Field	Value
Publication number	US-11502255-B2
Application number	US-201816488982-A
Country	US
Kind code	B2
Filing date	Nov 9, 2018
Priority date	Nov 28, 2017
Publication date	Nov 15, 2022
Grant date	Nov 15, 2022

Abstract

The present specification relates to a photoactive layer including: an electron donor; and an electron acceptor, in which the electron donor includes: a single molecular material; and a polymer material, and the single molecular material is represented by Formula 1, and an organic solar cell including the same.

First claim

What is claimed is:

1. A photoactive layer comprising:
an electron donor; and
an electron acceptor,
wherein the electron donor comprises a single molecular material and a polymer material,
wherein a content of the single molecular material in the electron donor is higher than a content of the polymer material and a volume ratio of the single molecular material to the polymer material is 99:1 to 51:49, and
wherein the single molecular material is a compound of Formula 1:

wherein:
n1 to n4 are each an integer from 1 to 3;
when n1 to n4 are each 2 or more, two or more structures in the parenthesis are the same as or different from each other;
X1 to X4 are the same as or different from each other, and are each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te;
Y1 to Y4 are the same as or different from each other, and are each independently CR c , N, SiR c , P, or GeR c ;
R1 to R8, R10 to R13, R a , R b , and R c are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
Ar1 and Ar2 are the same as or different from each other, and are each independently any one of the following structures,

wherein:
a is an integer from 1 to 4;
when a is 2 or more, two or more structures in the parenthesis are the same as or different from each other;
R101 to R106 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
[Push] has a structure which acts as an electron donor, and the structure is one of the following structures,

wherein:
b and c are each an integer from 1 to 3;
d, e, f, and g are each an integer from 1 to 5;
when b, c, d, e, f, and g are each 2 or more, two or more structures in the parenthesis are the same as or different from each other;
Z1 to Z12 are the same as or different from each other, and are each independently CR d R e , NR d , O, SiR d R e , PR d , S, GeR d R e , Se, or Te;
Z13 and Z14 are the same as or different from each other, and are each independently C, Si, or Ge; and
R201 to R208, R d , and R e are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

2. The photoactive layer of claim 1 , wherein the polymer material is a non-crystalline polymer material.

3. The photoactive layer of claim 2 , wherein the non-crystalline polymer material comprises a copolymer comprising a first unit of Formula 2 and a second unit of Formula 3:

wherein:
n10 and n11 are each an integer from 1 to 3;
when n10 and n11 are each 2 or more, two or more structures in the parenthesis are the same as or different from each other;
h and i are each an integer from 1 to 5;
when h and i are each 2 or more, two or more structures in the parenthesis are the same as or different from each other;
X10 to X13 are the same as or different from each other, and are each independently CR f R g , NR f , O, SiR f R g , PR f , S, GeR f R g , Se, or Te; and
R20 to R27, R f , and R g are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

4. The photoactive layer of claim 1 , wherein the polymer material is a crystalline polymer material.

5. The photoactive layer of claim 1 , wherein the compound of Formula 1 is a compound of Formula 1-1:

wherein:
n1 to n4, X1 to X4, Y1 to Y4, R1 to R8, R10 to R13, Ar1, and Ar2 are the same as those defined in Formula 1;
Z6 is CR d R e , NR d , O, SiR d R e , PR d , S, GeR d R e , Se, or Te;
b and c are each an integer from 1 to 3;
when b and c are each 2 or more, two or more structures in the parenthesis are the same as or different from each other; and
R203, R204, R d , and R e are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

6. The photoactive layer of claim 1 , further comprising an additive.

7. The photoactive layer of claim 1 , wherein the electron acceptor comprises a fullerene derivative.

8. An organic solar cell comprising:
a first electrode;
a second electrode on the first electrode; and
an organic material layer comprising one or more layers provided between the first electrode and the second electrode and comprising the photoactive layer according to claim 1 .

9. The organic solar cell of claim 8 , wherein the organic material layer further comprises a hole transport layer, a hole injection layer, or a layer which simultaneously transports and injects holes.

10. The organic solar cell of claim 8 , wherein the organic material layer further comprises an electron injection layer, an electron transport layer, or a layer which simultaneously injects and transports electrons.

11. The photoactive layer of claim 4 , wherein the crystalline polymer material comprises a copolymer comprising a unit of Formula 4:

wherein:
X20 and X21 are the same as or different from each other, and are each independently CR h R i , NR h , O, SiR h R i , PR h , S, GeR h R i , Se, or Te; and
R30 to R39, R h , and R i are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

12. The photoactive layer of claim 4 , wherein the crystalline polymer material comprises a copolymer comprising a unit of Formula 5:

Assignees

• Lg Chemical Ltd

Inventors

• Lim Bogyu
• Woo Han Young
• Jang Songrim
• Kim Kyungkon
• Kim Ji Hee

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0068

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic