Phillips 66 Company

Solarmer Energy, Inc.

Chenjun Shi

Ting He

Yue Wu

Hui Huang

Wei Wang

Kathy Woody

Amit Palkar

Joe Bullock

Jun Yang

Christopher Scot Daeffler

Janice Hawkins

Ruby Chen

Shuangxi Wang

Junlian Zhang

A method of making a fluorothieno[3,4-b]thiophene derivatives and photovoltaic polymers containing same using 3-bromothiophene-2-carboxylic acid as a starting material. This synthetic route provides an easier synthesis as well as greater yield and a purer product, which produces superior results over the prior art less pure products. The resulting materials can be used in a variety of photovoltaic applications and devices, especially solar cells.

Synthesis of photovoltaic conjugated polymers

A polymer having at least four different repeat units comprising: In this polymer R1, R2, R3 and R4 can be independently selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof and where the combination of R1, R2, R3 and R4 are not all identical. Additionally, in this polymer, m, n, o and p can be greater than 1. x and y are different from each other and can be independently selected from the group consisting of: of alkyl group, alkoxy group, aryl groups, where y=1-3, where y=0-12, where R5 is selected from the group consisting of H, of alkyl group, alkoxy group, aryl groups, where R6 is selected from the group consisting of H, alkyl, substituted alkyls, aryls and substituted aryls, where R7 and R8 are independently selected from the group consisting of H, of alkyl group, alkoxy group, aryl groups, &#x2014;NRRwhere R9 and R10 are independently selected from the group consisting of H, of alkyl group, alkoxy group, aryl groups.

Compositions and applications of a multi-component benzo[1,2-B:4,5-B] dithiophene-thienothiophene randomly substituted polymers for organic solar cells

Compositions, synthesis and applications for furan, thiophene and selenophene derivatized benzo[1,2-b:3,4-b']dithiophene(BDT)-thienothiophene (BDT-TT) based polymers, namely, poly[(4,8-bis(5-(2-ethyhexyl)selenophen-2-yl)-benzo[1,2-b;4,5-b&#x2032;]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexanoyl)-3-fluorothieno[3,4-b]thiophene)-2-6-diyl (CS-15), poly[(4,8-bis(5-(2-ethyhexyl)selenophen-2-yl)-benzo[1,2-b;4,5-b&#x2032;]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene)-2-carboxylate-2-6-diyl (CS-16), poly[(4,8-bis(5-(2-ethyhexyl)furan-2-yl)-benzo[1,2-b;4,5-b&#x2032;]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene)-2-carboxylate-2-6-diyl (CS-18) and poly[(4,8-bis(5-hexylfuran-2-yl)-benzo[1,2-b;4,5-b&#x2032;]dithiophene)-2,6-diyl-alt-(4-(2-ethylhexanoyl)-3-fluorothieno[3,4-b]thiophene)-2-6-diyl (CS-24) are disclosed. Further, an organic solar cell constructed of a derivatized benzo[1,2-b:3,4-b&#x2032;]dithiophene(BDT)-thienothiophene (BDT-TT) based polymer is discussed.

Furan and selenophene derivatized benzo [1,2-b:4,5-b']  dithiophene-thienothiophene based conjugated polymers for high-efficiency organic solar cells

A polymer having a monomer repeat unit comprising wherein Ar is an aryl group.

Difluorothienothiophene based conjugated polymers

A polymer having two different sets of repeat units consisting essentially of: In this polymer, R1, R2, R3 and R4 can be independently selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof. Also the combination of R1, R2, R3 and R4 are not all identical and n and o are greater than 1.

Composition and applications of a multi-component benzo[1,2-B:4,5-B] dithiophene-difluorothienothiophene randomly substituted polymers for organic solar cells

A process of polymerizing wherein the stoichiometric ratio of (f+g)&#x2248;(h+i) and f, g, h and i are not equal to 0. Additionally, R1, R2, R3 and R4 can be independently selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof and where the combination of R1, R2, R3 and R4 are not all identical. In addition, x and y can be different from each other and independently selected from the group consisting of: alkyl group, alkoxy group, aryl groups, where y=1-3, where y=0-12, where R5 is selected from the group consisting of H, alkyl group, alkoxy group, aryl groups, where R6 is selected from the group consisting of H, alkyl group, alkoxy group, aryl groups, where R7 and R8 are independently selected from the group consisting of H, alkyl group, alkoxy group, aryl groups, &#x2014;NRRwhere R9 and R10 are independently selected from the group consisting of H, alkyl group, alkoxy group, aryl groups.

Process of manufacturing and applications of a multi-component benzo[1,2-B:4,5-B] dithiphene-thienothiophene randomly substituted conjugated polymers for organic solar cells

A process of dissolving 3-fluoro-4,6-dihydrothieno[3,4-b]thiophene in a solvent to create a solution. An initiator is then added to the solution to produce an initiated solution followed by adding a fluorinated chemical to the initiated solution to produce 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene. 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene is then oxidized with an oxidant to produce 2,3-difluorothieno[3,4-b]thiophene. A brominating step then occurs to the 2,3-difluorothieno[3,4-b]thiophene to produce 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene is then debrominated and polymerized to The stoichiometric ratio of (f+g)&#x2248;h and f, g and h are not equal to 0. Additionally, in this embodiment R1, R2, R3 and R4 are independently selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof and where the combination of R1, R2, R3 and R4 are not all identical.

Process of producing and applications of a multi-component benzo[1,2-B:4,5-B] difluorothienothiophene randomly substituted polymers for organic solar cells

A method of producing a monomer wherein the method begins by dissolving 3-fluoro-4,6 dihydrothieno[3,4-b]thiophene in a solvent to create a solution. An initiator is then added to the solution to produce an initiated solution. This is followed by adding a fluorinated chemical to the initiated solution to produce 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene. 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene is then oxidized with an oxidant to produce 2,3-difluorothieno[3,4-b]thiophene. 2,3-difluorothieno[3,4-b]thiophene is then bromoated to produce 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene. The final step involves debrominating 4,6-dibromo-2,3-difluorothieno[2,3-c]thiophene and adding an aryl group to produce the monomer 

Process of making difluorothienothiophene based conjugated polymers

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&#x2032;]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&#x2032;]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&#x2032;]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&#x2032;]dithiophene (ADT) based polymer is discussed.

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La Puente, CA, United States of America

Chenjun Shi