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    High performance wide-bandgap polymers for organic photovoltaics
    3.
    发明授权
    High performance wide-bandgap polymers for organic photovoltaics 有权

    公开(公告)号：US11274178B2

    公开(公告)日：2022-03-15

    申请号：US16038364

    申请日：2018-07-18

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Kathy Woody ,  Laura Nielsen ,  Hualong Pan ,  Taeshik Earmme

    IPC: C08G61/12 ,  H01L51/00 ,  H01L51/42

    Abstract: A copolymer comprising a repeat unit A, wherein repeat unit A comprises a repeat unit B, wherein repeat unit B comprises and at least one optional repeat unit D, wherein repeat unit D comprises an aryl group. In this copolymer, X1, X2, X3, and X4 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups and R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups.

    Method of producing benzo[1,2-B:4,5-B′]dithiophene and benzothiadiazole-based molecular complexes
    5.
    发明授权
    Method of producing benzo[1,2-B:4,5-B′]dithiophene and benzothiadiazole-based molecular complexes 有权

    公开(公告)号：US09908857B2

    公开(公告)日：2018-03-06

    申请号：US15644153

    申请日：2017-07-07

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody ,  Brian Worfolk ,  Taeshik Earmme

    IPC: C07D285/14 ,  C07D417/14 ,  C07D495/04 ,  H01L51/00

    CPC classification number: C07D285/14 ,  C07D417/14 ,  C07D495/04 ,  H01L51/0036 ,  H01L51/0043 ,  H01L51/0047 ,  H01L51/4253

    Abstract: A method of forming a molecular complex. The method proceeds by reacting 5-chloro-2,1,3-benzothiadiazole with N-bromosuccinimide to produce 4,7-dibromo-5-chlorobenzo[c][1,2,5]thiadiazole. 4,7-dibromo-5-chlorobenzo[c][1,2,5]thiadiazole is then reacted with trimethyl[4-(2-octyldodecyl)thiophen-2-yl]stannane to produce 5-chloro-4,7-bis(4-(2-octyldodecyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole. 4, 7-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole is subsequently synthesized from 5-chloro-4,7-bis(4-(2-octyldodecyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole. 4,7-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole with tributyl(thiophen-2-yl)stannane is then reacted to produce 4-bromo-5,6-difluoro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole. This is followed by reacting 4,7-dibromo-5-chloro-2,1,3-benzothiadiazole with tributyl(thiophen-2-yl)stannane to produce 4-bromo-5-chloro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole. trimethyl[4-(2-octyldodecyl)thiophen-2-yl]stannane is then reacted with and 4-bromo-5-chloro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole to produce 5-chloro-4-(4-(2-octyldodecyl)thiophen-2-yl)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole. 5-chloro-4-(4-(2-octyldodecyl)thiophen-2-yl)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole is then reacted with N-bromosuccinimide to produce the co-monomer 4-(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-7-(5-bromothiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole. A group can then be coupled to 4-(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-7-(5-bromothiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole to produce a molecular complex.

    Unsymmetrical benzothtadiazole-based random copolymers
    6.
    发明授权
    Unsymmetrical benzothtadiazole-based random copolymers 有权

    公开(公告)号：US11639421B2

    公开(公告)日：2023-05-02

    申请号：US17238578

    申请日：2021-04-23

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody ,  Brian Worfolk ,  Taeshik Earmme

    IPC: C08G75/32 ,  C08G75/06

    Abstract: A random copolymer comprising the monomer units A and B. In this random copolymer A comprises and B comprises Additionally, R1 R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are different and at least one is a Cl and the other is selected from the group consisting of: H, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.

    Unsymmetrical benzothiadiazole-based molecular complexes in organic photovoltaic devices
    10.
    发明授权
    Unsymmetrical benzothiadiazole-based molecular complexes in organic photovoltaic devices 有权

    公开(公告)号：US10361370B2

    公开(公告)日：2019-07-23

    申请号：US15644253

    申请日：2017-07-07

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody ,  Brian Worfolk ,  Taeshik Earmme ,  Joseph E. Bullock

    IPC: H01L51/00 ,  C08G61/12 ,  H01L51/42 ,  H01L51/44

    Abstract: An organic photovoltaic device comprising an electron transport layer disposed between an anode and a polymer layer. In this organic photovoltaic device the polymer layer can also be disposed between the electron transport layer and a cathode. The electron transport layer comprises (AOx)yBO(1-y) with an optional fullerene dopant. The polymer comprises a molecular complex comprising wherein X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups; R1, R2, R1′ and R2′ are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups; R3 are selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof; G is an aryl group; and wherein the thiophene groups are unsymmetrical.

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