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    High performance wide-bandgap polymers for organic photovoltaics
    12.
    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 synthesis for organic semiconducting polymers
    13.
    发明授权
    Method of synthesis for organic semiconducting polymers 有权

    公开(公告)号：US11211562B2

    公开(公告)日：2021-12-28

    申请号：US17003059

    申请日：2020-08-26

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody

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

    Abstract: A method of forming a polymer, the method comprising combining 4-bromo-7-[5-bromo-4-(alkyl)thiophen-2-yl]-6-chloro-5-fluoro-2,1,3-benzothiadiazole, (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane), [4-(alkyl)-5-[5-(trimethylstannyl)thiophen-2-yl]thiophen-2-yl]trimethylstannane, tris(dibenzylideneacetone), and dipalladium P(o-tol)3 tris(2-methylphenyl)phosphane to form the polymer: In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, Q is selected from the group consisting of: a straight-chain carbyl, silyl or hydrocarbyl, branched, cyclic alkyl with 1 to 30 atoms, and fused aromatic rings. Furthermore in this polymer, R1, and R4 are independently selected from the group consisting of: F, Cl, I, Br, CN, —NCO, —NCS, —OCN, —SCN, —OX, —SX, —NH2, —C(═O)X, —C(═O)—OX, —OX, —NHX, —NXX′, —C(═O)NHX, —C(═O)NXX′, —SO3X, —SO2X, —OH, —NO2, CF3, —SF5, a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. This polymer can also have R2 and R3 are independently selected from F, Cl, Br and I. Additionally, in this polymer, the fused aromatic rings can be independently fused with groups consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Lastly, in this polymer, h+j is between 0.2 to 0.6 and i+k is between 0.4 and 0.8.

    Method of synthesis for organic semiconducting polymers
    14.
    发明授权
    Method of synthesis for organic semiconducting polymers 有权

    公开(公告)号：US11168178B2

    公开(公告)日：2021-11-09

    申请号：US17002999

    申请日：2020-08-26

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody

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

    Abstract: A method of forming a polymer, the method comprising combining 4,7-bis(5-bromo-4-alkyl thiophen-2-yl)-5-chloro-6-fluorobenzo[c][1,2,5]thiadiazole, (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane), and benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(trimethylstannane), Pd2dba3 and P(o-tol)3 to form the polymer: In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, in this polymer Q is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. R1, R2, R3, R4, and R5 are independently selected from the group consisting of: F, Cl, I, Br, CN, —NCO, —NCS, —OCN, —SCN, —OX, —SX, —NH2, —C(═O)X, —C(═O)—OX, —OX, —NHX, —NXX′, —C(═O)NHX, —C(═O)NXX′, —SO3X, —SO2X, —OH, —NO2, CF3, —SF5, a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring, and heteroaromatic rings. Additionally, in this polymer wherein the fused aromatic rings can be independently fused with groups consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring; and the ratio of x is between 0.6 to 0.8 and y is between 0.2 and 0.4.

    METHOD OF SYNTHESIS FOR ORGANIC SEMICONDUCTING POLYMERS
    16.
    发明申请
    METHOD OF SYNTHESIS FOR ORGANIC SEMICONDUCTING POLYMERS 有权

    公开(公告)号：US20210066609A1

    公开(公告)日：2021-03-04

    申请号：US17003059

    申请日：2020-08-26

    Applicant: PHILLIPS 66 COMPANY

    Inventor： Hualong Pan ,  Kathy Woody

    IPC: H01L51/00 ,  C08G61/12

    Abstract: A method of forming a polymer, the method comprising combining 4-bromo-7-[5-bromo-4-(alkyl)thiophen-2-yl]-6-chloro-5-fluoro-2,1,3-benzothiadiazole, (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane), [4-(alkyl)-5-[5-(trimethylstannyl)thiophen-2-yl]thiophen-2-yl]trimethylstannane, tris(dibenzylideneacetone), and dipalladium P(o-tol)3 tris(2-methylphenyl)phosphane to form the polymer: In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, Q is selected from the group consisting of: a straight-chain carbyl, silyl or hydrocarbyl, branched, cyclic alkyl with 1 to 30 atoms, and fused aromatic rings. Furthermore in this polymer, R1, and R4 are independently selected from the group consisting of: F, Cl, I, Br, CN, —NCO, —NCS, —OCN, —SCN, —OX, —SX, —NH2, —C(═O)X, —C(═O)—OX, —OX, —NHX, —NXX′, —C(═O)NHX, —C(═O)NXX′, —SO3X, —SO2X, —OH, —NO2, CF3, —SF5, a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. This polymer can also have R2 and R3 are independently selected from F, Cl, Br and I. Additionally, in this polymer, the fused aromatic rings can be independently fused with groups consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Lastly, in this polymer, h+j is between 0.2 to 0.6 and i+k is between 0.4 and 0.8.

    Method of producing benzo[1,2-B:4,5-B′]dithiophene and benzothiadiazole-based molecular complexes
    18.
    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.

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