Symmetric charge transfer compounds for organic photovoltaics

Patent metadata

Field	Value
Publication number	US-12317738-B2
Application number	US-202117386183-A
Country	US
Kind code	B2
Filing date	Jul 27, 2021
Priority date	Jul 30, 2020
Publication date	May 27, 2025
Grant date	May 27, 2025

Abstract

The present disclosure is related to organic acceptor-donor-acceptor compounds as non-fullerene acceptors for use in organic photovoltaics.

First claim

We claim:

1. A compound represented by Formula (A-I):

wherein
E is a core chromophore group represented by Formula (E-1);
A is an electron accepting group represented by a formula selected from the group consisting of Formula (A-4) to Formula (A-9):

wherein, in Formula (A-4) to Formula (A-9),
each R 1 to R 2 independently represents mono to the maximum allowable substitution;
each R and R 1 to R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino and combinations thereof;
wherein any two adjacent R or R 1 to R 4 are optionally joined or fused together to form a ring which is optionally substituted;
each X 1 to X 8 independently represents C, Si, N or P; and
each Z 1 , Z 2 , and Z 3 independently represents CR 2 , NR, O, or S;
π is a linking group;
m is an integer from 0 to 3; and
p is an integer from 1 to 3;
wherein each A is the same and each π is the same

wherein, in Formula (E-1):
each R 1 and R 2 independently represents mono to the maximum allowable substitution;
each R 1 and R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino and combinations thereof;
wherein any two adjacent R 1 or R 2 are optionally joined or fused together to form a ring which is optionally substituted
each R M independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino and combinations thereof;
X 1 represents C, Si, N or P; and
M is a monovalent, divalent, trivalent or tetravalent atom.

2. The compound of claim 1 , wherein M is selected from the group consisting of B, Al, C, Si, Ge, Ti, Zr, Hf, Zn, Cd, Ca, Cu, Ag and Au; or
wherein each R M independently represents hydrogen or a substituent selected from the group consisting of halogen, pseudohalogen, alkyl, alkenyl, alkynyl, aryl, alkoxy, hydroxyl, and combinations thereof.

3. The compound of claim 1 , wherein A is a group represented by Formula (A-6) or (A-7)

4. The compound of claim 1 , wherein x is a group represented by a formula selected from the group consisting of Formula (P-1) to Formula (P-11):

each R 1 to R 4 independently represents mono to the maximum allowable substitution;
each R and R 1 to R 2 independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, pseudohalogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, amide, hydroxyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, benzoyl, ether, ester, vinyl, ketone, sulfinyl, sulfonyl, cyano, phosphino and combinations thereof;
wherein any two adjacent R or R 1 to R 4 are optionally joined or fused together to form a ring which is optionally substituted;
each X 1 to X 8 independently represents C, Si, N or P; and
each Z 1 and Z 2 independently represents CR 2 , NR, O, or S.

5. The compound of claim 1 , wherein A is selected from the group consisting of

and E is

wherein Ar is an aryl group.

6. The compound of claim 1 , wherein the compound is selected from the group consisting of:

7. An organic photovoltaic device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound according to claim 2 .

8. A formulation comprising the compound of claim 1 .

Assignees

• Univ Southern California

Inventors

• Thompson Mark E
• Mencke Austin

Classifications

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K30/20

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/00

  Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation (integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20) · CPC title

• H10K85/322 Primary

  comprising boron · CPC title