Synthesis of porphyrin materials for highly efficient organic photovoltaics

Patent metadata

Field	Value
Publication number	US-10236457-B2
Application number	US-201715635563-A
Country	US
Kind code	B2
Filing date	Jun 28, 2017
Priority date	Jun 29, 2016
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

Abstract

The present disclosure relates to porphyrin small molecules that can be represented by, e.g., a compound of Formula IV designed and synthesized for bulk heterojunction (BHJ) organic solar cells (OSCs). Provided are synthesized materials with strong and ordered self-assembly property, leading to form bi-continuous, interpenetrating networks which are required for efficient charge separation and transport in organic solar cells. The power conversion efficiency (PCE) of the solar cells devices based on the embodiments of the present disclosure have the highest PCE among the solution-processed BHJ solar cell based on porphyrin small molecules to date.

First claim

We claim:

1. A porphyrin small molecule having a molecular formula represented by Type 1, Type 2, Type 3, or Type 4:

wherein,
m is an integer selected from 2, 3, 4, or 5;
M is selected from the group consisting of Fe 2+ , Co 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Ru 2+ , Pd 2+ , and Pt 2+ ;
Ar 1 for each occurrence is independently selected from the group consisting of:

Ar 2 for each occurrence is independently selected from the group consisting of:

A 1 for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, R 3 , —CH(R 3 )(R 4 ), —CH 2 CH(R 3 )(R 4 ), —CH 2 CH 2 CH(R 3 )(R 4 ), —CH 2 (OCH 2 CH 2 ) n OCH 3 , —CH 2 (CH 2 ) n CF 3 , and —CF 2 (CF 2 ) 5 CF 3 , wherein n is an integer number ranging from 0 to 20;
A 2 for each instance is independently selected from the group consisting from the group consisting of:

A 3 for each instance is independently selected from the group consisting of:

each instance of R 1 , R 2 , R 5 , and R 6 , is independently selected from the group consisting of hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, haloaryl, aryloxy, halogenated aryloxy, cycloalkyl, heterocyclic alkyl, halogenated heterocyclic alkyl, heterocyclic alkoxy, halogenated heterocyclic alkoxy, heteroaryl, halogenated heteroaryl, heteroaryloxy, halogenated heterocyclic aryloxy, amino, halogenated amino, nitro,

and
R 3 and R 4 are independently selected from the group consisting of C 1 -C 20 alkyl, cycloalkyl, alkoxyl, aryloxyl, thioalkoxyl, and thioaryloxyl.

2. The porphyrin small molecule according to claim 1 , wherein said porphyrin small molecule has a molecular formula represented by Formula I:

wherein, A 1 for each instance is independently selected from the group consisting of:

3. The porphyrin small molecule according to claim 1 , wherein said porphyrin small molecule has a molecular formula represented by formula II or III:

4. The porphyrin small molecule of claim 1 , wherein said porphyrin small molecule has a molecular formula represented by IV or V:

5. The porphyrin small molecule of claim 1 wherein said porphyrin small molecule has a molecular formula represented by the structure VI:

6. A method of preparing the porphyrin small molecule of claim 2 , comprising the steps of:
contacting a compound with molecular formula VII:

with 3-ethylrhodanine or a conjugate base thereof, and optionally a base thereby forming the porphyrin small molecule of claim 2 , wherein Ai is as defined in claim 2 .

7. A method of preparing the porphyrin small molecule of claim 3 , comprising the steps of:
contacting a compound of formula VIII:

3-ethylrhodanine or 2-(1,1-dicyanomethylene), 3-ethylrhodanine or a conjugate base thereof, and optionally a base thereby forming the porphyrin small molecule of claim 3 .

8. A method of preparing the porphyrin small molecule of claim 4 comprising the steps of:
contacting a compound of formula IX or X:

3-ethylrhodanine or a conjugate base thereof, and optionally a base thereby forming the porphyrin small molecule of claim 4 .

9. A method of preparing the porphyrin small molecule of claim 5 comprising the steps of:
contacting a compound of formula XI:

3-ethylrhodanine or a conjugate base thereof, and optionally a base thereby forming the porphyrin small molecule of claim 5 .

10. A bulk heterojunction (BHJ) organic solar cell comprising a porphyrin small molecule of claim 1 .

11. A bulk heterojunction (BHJ) organic solar cell comprising a porphyrin small molecule of claim 2 .

12. A bulk heterojunction (BHJ) organic solar cell comprising a porphyrin small molecule of claim 3 .

13. A bulk heterojunction (BHJ) organic solar cell comprising a porphyrin small molecule of claim 4 .

14. A bulk heterojunction (BHJ) organic solar cell comprising a porphyrin small molecule of claim 5 .

Assignees

• Univ Hong Kong Baptist Univ

Inventors

• Zhu Xunjin
• Chen Song
• Wong Wai Yeung
• Wong Wai Kwok

Classifications

• C09B47/00

  Porphines; Azaporphines {(non-dyeing compounds C07D487/22)} · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B3/78

  Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01G9/20

  Light-sensitive devices · CPC title