公开(公告)号：US20200017632A1

公开(公告)日：2020-01-16

申请号：US16511418

申请日：2019-07-15

Applicant: PHILLIPS 66 COMPANY

Inventor： Kathy Woody ,  Laura Nielsen ,  Hualong Pan

IPC: C08G61/12 ,  H01L51/00

Abstract: A novel AB-type copolymer for use in organic photovoltaics. The AB-type copolymer comprisesa unit A, where the unit A is where R1 is a carbon chain from about 1 to about 30 units and where Y is selected from CN, F and Cl. The B unit of the AB-type copolymer is selected from is selected from: wherein X1, X2, X3, and X4 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkylthiol, alkoxy, ester, ketone, amide and aryl groups.

公开(公告)号：US10358444B2

公开(公告)日：2019-07-23

申请号：US15644186

申请日：2017-07-07

Applicant: PHILLIPS 66 COMPANY

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

IPC: C07D417/14 ,  C07D285/14 ,  H01L51/00 ,  H01L51/42

Abstract: 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; G is an aryl group; and wherein the thiophene groups are unsymmetrical.

公开(公告)号：US20180026194A1

公开(公告)日：2018-01-25

申请号：US15644230

申请日：2017-07-07

Applicant: PHILLIPS 66 COMPANY

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

IPC: H01L51/00 ,  C08G61/12

Abstract: 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; and wherein the thiophene groups are unsymmetrical.

公开(公告)号：US20180022718A1

公开(公告)日：2018-01-25

申请号：US15644186

申请日：2017-07-07

Applicant: PHILLIPS 66 COMPANY

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

IPC: C07D285/14 ,  H01L51/00

CPC classification number: C07D417/14 ,  C07D285/14 ,  H01L51/0036 ,  H01L51/0047 ,  H01L51/4253 ,  Y02E10/549

Abstract: 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; G is an aryl group; and wherein the thiophene groups are unsymmetrical.

公开(公告)号：US20180022717A1

公开(公告)日：2018-01-25

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 ,  C07D495/04 ,  H01L51/00 ,  C07D417/14

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.

公开(公告)号：US11849629B2

公开(公告)日：2023-12-19

申请号：US17530940

申请日：2021-11-19

Applicant: PHILLIPS 66 COMPANY

Inventor： Laura Nielsen ,  Reed Eisenhart ,  Victoria Suding ,  Hualong Pan ,  Alyssa Chinen-Mendez

IPC: H10K85/10 ,  C08G61/12 ,  H10K30/30

CPC classification number: H10K85/113 ,  C08G61/126 ,  H10K85/151 ,  C08G2261/124 ,  C08G2261/146 ,  C08G2261/149 ,  C08G2261/1412 ,  C08G2261/18 ,  C08G2261/228 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/3246 ,  C08G2261/91 ,  H10K30/30

Abstract: A method of reacting




with





to produce





In this method Y1 and Y2 are independently selected from the group consisting of: H, Cl, Br, I, and combinations thereof. Additionally in this method M is selected from the group consisting of H, trialkylstannane, boronate, or ZnX, wherein X is Cl, Br, or I. Furthermore in this method Z is a divalent linking group selected from the group consisting of:





Lastly, in this method R1 is selected from: H, unsubstituted or substituted branched alkyls with 1 to 60 carbon atoms or unsubstituted or substituted linear alkyls with 1 to 60 carbon atoms.

公开(公告)号：US11716895B2

公开(公告)日：2023-08-01

申请号：US17238430

申请日：2021-04-23

Applicant: PHILLIPS 66 COMPANY

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

IPC: H10K85/10 ,  C08G61/12 ,  H10K30/30

CPC classification number: H10K85/113 ,  C08G61/123 ,  C08G61/126 ,  H10K85/151 ,  C08G2261/122 ,  C08G2261/124 ,  C08G2261/146 ,  C08G2261/149 ,  C08G2261/1412 ,  C08G2261/1424 ,  C08G2261/314 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/3246 ,  C08G2261/414 ,  C08G2261/91 ,  H10K30/30 ,  Y02E10/549

Abstract: A random copolymer comprising the monomer units A, B and C. In this random copolymer A comprises




B comprises





and C comprises an aryl group. 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 independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.

公开(公告)号：US11702413B2

公开(公告)日：2023-07-18

申请号：US17002805

申请日：2020-08-26

Applicant: PHILLIPS 66 COMPANY

Inventor： Hualong Pan ,  Kathy Woody ,  Brian J. Worfolk

IPC: C07D417/14

CPC classification number: C07D417/14

Abstract: A comonomer comprising:




wherein W is selected from the group consisting of: S, Se, O, and N-Q; and 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. In this comonomer, A and B are independently selected from the group consisting of: H, Br, an aryl group, and a heteroaryl group.

公开(公告)号：US11678562B2

公开(公告)日：2023-06-13

申请号：US17003066

申请日：2020-08-26

Applicant: PHILLIPS 66 COMPANY

Inventor： Hualong Pan ,  Kathy A. Repa ,  Brian J. Worfolk ,  Alyssa Brooke Chinen-Mendez

IPC: H10K85/10 ,  C08K9/04 ,  C08K3/04 ,  C08G61/12 ,  H10K85/20 ,  H10K85/60 ,  H10K30/00 ,  H10K50/15 ,  H10K50/16

CPC classification number: H10K85/113 ,  C08G61/126 ,  C08K3/045 ,  C08K9/04 ,  H10K85/151 ,  H10K85/215 ,  H10K85/6576 ,  C08G2261/122 ,  C08G2261/145 ,  C08G2261/149 ,  C08G2261/1426 ,  C08G2261/18 ,  C08G2261/228 ,  C08G2261/314 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/334 ,  C08G2261/411 ,  C08G2261/51 ,  C08G2261/514 ,  C08G2261/91 ,  C08K2201/001 ,  C08K2201/011 ,  H10K30/00 ,  H10K50/15 ,  H10K50/16

Abstract: An organic photovoltaic device comprising a polymer:




and an acceptor. In this organic photovoltaic device, R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of: a halogen, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl and an unsubstituted heteroaryl.

公开(公告)号：US20230094872A1

公开(公告)日：2023-03-30

申请号：US17903691

申请日：2022-09-06

Applicant: PHILLIPS 66 COMPANY

Inventor： Laura Nielsen ,  Reed Eisenhart ,  Victoria Suding ,  Alyssa Brooke Chinen-Mendez ,  Brian J. Worfolk ,  Zach L. Cramer ,  Hualong Pan

IPC: C08G61/12 ,  H01L51/00

Abstract: A polymer comprising In this polymer, R, R′, and R″ are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. Additionally, in this polymer X and X′ are independently selected from aryl groups. Finally, m independently ranges from 1 to 100 and n independently ranges from 0 to 99