Anthradithiophene-based semiconducting polymers and methods thereof

Patent metadata

Field	Value
Publication number	US-9214635-B2
Application number	US-201414532229-A
Country	US
Kind code	B2
Filing date	Nov 4, 2014
Priority date	Nov 21, 2013
Publication date	Dec 15, 2015
Grant date	Dec 15, 2015

Abstract

Compositions, synthesis and applications for benzene, furan, thiophene, selenophene, pyrole, pyran, pyridine, oxazole, thiazole and imidazole derivatized anthra[2,3-b:6,7-b′]dithiophene (ADT) based polymers, namely, poly{5,11-bis(5-(2-ethylhexyl)thiophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl}, poly{5,11-bis(5-(2-ethylhexyl)furan-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl and poly{5,11-bis(5-(2-ethylhexyl)selenophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl} are disclosed. Further, an organic solar cell constructed of a derivatized anthra[2,3-b:6,7-b′]dithiophene (ADT) based polymer is discussed.

First claim

What is claimed is:

1. A derivatized anthra[2,3-b:6,7-b′]dithiophene (ADT) based monomer having the formula

wherein Ar is selected from the group consisting of benzene, furan, thiophene, selenophene, pyrole, pyran, pyridine, oxazole, thiazole, imidazole and derivatives thereof, wherein Ar′ is selected from the group consisting of thieno[3,4-b]thiophene, benzothiadiazole, thieno[3,4-c]pyrrole-4,6(5H)-dione and derivatives thereof.

2. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar is selected from the group consisting of benzene, thiophene, pyrole, pyridine, thiazole and derivatives thereof.

3. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar is selected from the group consisting of thiophene and derivatives thereto.

4. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar is selected from the group consisting of furan and derivatives thereto.

5. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar is selected from the group consisting of selenophene and derivatives thereto.

6. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar comprises R selected from the group consisting of hydrogen, C1 to C15 alkyls and C1 to C15 alkoxys; and wherein Ar′ comprises R and R′ both selected from the group consisting of hydrogen, C1 to C15 alkyls and C1 to C15 alkoxys.

7. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 , wherein Ar comprises R selected from the group consisting of C4 to C10 alkyls and C4 to C10 alkoxys; and wherein Ar′ comprises R and R′ both selected from the group consisting of C4 to C10 alkyls and C4 to C10 alkoxys.

8. The derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer of claim 1 ,
wherein the derivatized anthra[2,3-b:6,7-b′]dithiophene based monomer is formed into a derivatized anthra[2,3-b:6,7-b′]dithiophene based polymer having the formula

wherein n is equal to 1 to 100.

9. The derivatized anthra[2,3-b:6,7-b′]dithiophene based polymer of claim 8 , wherein n is equal to 1 to 50.

10. A bulk heterojunction material, comprising:
a) at least one derivatized anthra[2,3-b:6,7-b′]dithiophene based polymer as in claim 1 as a donor; and
b) an acceptor.

11. The bulk heterojunction material of claim 10 , wherein the anthra[2,3-b:6,7-b′]dithiophene based polymer is selected from the group consisting of poly{5,11-bis(5-(2-ethylhexyl)furan-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl}, poly{5,11-bis(5-(2-ethylhexyl)thiophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl} and poly{5,11-bis(5-(2-ethylhexyl) selenophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl}.

12. The bulk heterojunction material of claim 10 , wherein the acceptor is selected from the group consisting of PC 70 BM, BisIndene-C 70 , BisPC 70 BM, BisBenzene-C 70 , TrisPC 70 BM and PC 76 BM.

13. An organic solar cell device comprising:
a) an aluminum or silver layer;
b) a bulk heterojunction layer, wherein the bulk heterojunction layer comprises:
i. at least one derivatized anthra[2,3-b:6,7-b′]dithiophene based polymer as in claim 1 as a donor; and
ii. an acceptor; and

c) an indium tin oxide glass layer.

14. The organic solar cell device of claim 13 , wherein the anthra[2,3-b:6,7-b′]dithiophene based polymer is selected from the group consisting of poly{5,11-bis(5-(2-ethylhexyl)furan-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl}, poly{5,11-bis(5-(2-ethylhexyl)thiophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl} and poly{5,11-bis(5-(2-ethylhexyl) selenophen-2-yl)anthra[2,3-b:6,7-b′]dithiophene-2,8-diyl-alt-2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one-4,6-diyl}.

15. The organic solar cell device of claim 13 , wherein the acceptor is selected from the group consisting of PC 70 BM, BisIndene-C 70 , BisPC 70 BM, BisBenzene-C 70 , TrisPC 70 BM and PC 76 BM.

Assignees

• Phillips 66 Co
• Solarmer Energy Inc

Inventors

• Shi Chenjun
• Chen Ruby
• Yang Jun
• Daeffler Christopher S
• Hawkins Janice
• Wu Yue
• Wang Wei
• Woody Kathy
• Bullock Joe
• Huang Hui
• Palkar Amit
• He Ting

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title