公开(公告)号：US20180026195A1

公开(公告)日：2018-01-25

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

CPC classification number: H01L51/0036 ,  H01L51/0003 ,  H01L51/0028 ,  H01L51/0031 ,  H01L51/0047 ,  H01L51/4246 ,  H01L51/4253 ,  H01L51/441 ,  Y02E10/549

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.

公开(公告)号：US09537099B2

公开(公告)日：2017-01-03

申请号：US14722409

申请日：2015-05-27

Applicant: PHILLIPS 66 COMPANY

Inventor： Kathy Woody ,  Hui Huang ,  Ting He

IPC: C08G75/00 ,  H01L51/00 ,  H01L51/42

CPC classification number: H01L51/0036 ,  H01L51/0043 ,  H01L51/4253 ,  Y02E10/549

Abstract: A polymer having two different sets of repeat units consisting essentially of: Additionally, in the polymer R1 can be selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof. In the polymer, n and m can be greater than 1.In the polymer, x and y can be different from each other and independently selected from the group consisting of: an alkoxy group, a substituted alkoxy group, an aryl group, an alkyl group, a substituted alkyl group, where y=1-3, where y=0-12, where R2 is selected from the group consisting of H, alkyl groups, and aryl groups, where R3 is selected from the group consisting of H, alkyl groups, and aryl groups, where R4 and R5 are independently selected from the group consisting of H, alkyl groups, and aryl groups, —NR6R7 where R6 and R7 are independently selected from the group consisting of H, alkyl groups, and aryl groups.

Abstract translation: 具有两个不同组的重复单元的聚合物，其基本上由以下组成：另外，在聚合物R1中可以选自烷基，烷氧基，芳基及其组合。 在聚合物中，n和m可以大于1.在聚合物中，x和y可以彼此不同并且独立地选自：烷氧基，取代的烷氧基，芳基，烷基 基团，取代的烷基，其中y = 1-3，其中y = 0-12，其中R 2选自H，烷基和芳基，其中R 3选自H， 烷基和芳基，其中R 4和R 5独立地选自H，烷基和芳基，-NR 6 R 7，其中R 6和R 7独立地选自H，烷基和芳基 。

公开(公告)号：US20150344616A1

公开(公告)日：2015-12-03

申请号：US14722699

申请日：2015-05-27

Applicant: PHILLIPS 66 COMPANY ,  SOLARMER ENERGY, INC.

Inventor： Kathy Woody ,  Hui Huang ,  Ting He ,  Wei Wang ,  Chenjun Shi ,  Yue Wu

IPC: C08G61/12 ,  H01L51/00

CPC classification number: C08G61/126 ,  C08G2261/12 ,  C08G2261/1426 ,  C08G2261/1428 ,  C08G2261/146 ,  C08G2261/149 ,  C08G2261/18 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/414 ,  C08G2261/91 ,  H01L51/0036 ,  H01L51/0043 ,  H01L51/4253 ,  Y02E10/549

Abstract: A process of polymerizing wherein the stoichiometric ratio of (f+g)≈(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, —NR9R10 where R9 and R10 are independently selected from the group consisting of H, alkyl group, alkoxy group, aryl groups.

Abstract translation: （f + g）≈（h + i）和f，g，h和i的化学计量比不等于0的聚合过程。另外，R 1，R 2，R 3和R 4可以独立地选自 由烷基，烷氧基，芳基及其组合组成，其中R1，R2，R3和R4的组合不完全相同。 此外，x和y可以彼此不同并且独立地选自：烷基，烷氧基，芳基，其中y = 1-3，其中y = 0-12，其中R 5选自 由H，烷基，烷氧基，芳基组成的基团，其中R 6选自H，烷基，烷氧基，芳基，其中R 7和R 8独立地选自H，烷基 烷氧基，芳基，-NR 9 R 10，其中R 9和R 10独立地选自H，烷基，烷氧基，芳基。

公开(公告)号：US20150344495A1

公开(公告)日：2015-12-03

申请号：US14722919

申请日：2015-05-27

Applicant: PHILLIPS 66 COMPANY ,  SOLARMER ENERGY, INC.

Inventor： Wei Wang ,  Jun Yang ,  Chenjun Shi ,  Christopher Daeffler ,  Janice Hawkins ,  Yue Wu ,  Ting He ,  Hui Huang ,  Amit Palkar ,  Kathy Woody ,  Joe Bullock

IPC: C07D495/04

CPC classification number: C07D495/04

Abstract: 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

Abstract translation: 制备单体的方法，其中该方法开始于将3-氟-4,6-二氢噻吩并[3,4-b]噻吩溶于溶剂中以产生溶液。 然后将引发剂加入到溶液中以产生引发的溶液。 然后在引发的溶液中加入氟化物，生成2,3-二氟-4,6-二氢噻吩并[3,4-b]噻吩。 然后用氧化剂氧化2,3-二氟-4,6-二氢噻吩并[3,4-b]噻吩，得到2,3-二氟噻吩并[3,4-b]噻吩。 然后将2,3-二氟噻吩并[3,4-b]噻吩溴化，得到4,6-二溴-2,3-二氟噻吩并[2,3-c]噻吩。 最后一步涉及脱溴4,6-二溴-2,3-二氟噻吩并[2,3-c]噻吩并加入芳基来制备单体

公开(公告)号：US20150136224A1

公开(公告)日：2015-05-21

申请号：US14532229

申请日：2014-11-04

Applicant: Phillips 66 Company ,  Solarmer Energy, Inc.

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

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

CPC classification number: H01L51/0036 ,  C08G61/126 ,  C08G2261/12 ,  C08G2261/18 ,  C08G2261/3243 ,  C08G2261/91 ,  C09K11/06 ,  C09K2211/1458 ,  H01L51/0043 ,  H01L51/0074 ,  H01L51/4253 ,  H01L2251/308 ,  Y02E10/549

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.

Abstract translation: 苯，呋喃，噻吩，硒吩，吡咯，吡喃，吡啶，恶唑，噻唑和咪唑衍生化的蒽[2,3-b：6,7-b']二噻吩（ADT）基聚合物的组合物，合成和应用， 聚[5,11-双（5-（2-乙基己基）噻吩-2-基）蒽[2,3-b：6,7-b']二噻吩-2,8-二基-2-乙基-2-乙基 - 1-（噻吩并[3,4-b]噻吩-2-基）己-1-酮-4,6-二基}，聚{5,11-双（5-（2-乙基己基）呋喃-2-基 ）噻吩[2,3-b：6,7-b']二噻吩-2,8-二基-2-乙基-1-（噻吩并[3,4-b]噻吩-2-基）己烷-1 - 酮-4,6-二基和聚{5,11-双（5-（2-乙基己基）硒吩-2-基）蒽[2,3-b：6,7-b']二噻吩-2,8 - 二基-2-乙基-1-（噻吩并[3,4-b]噻吩-2-基）己-1-酮-4,6-二基}。 此外，讨论了由衍生的蒽[2,3-b：6,7-b']二噻吩（ADT）基聚合物构成的有机太阳能电池。

公开(公告)号：US11091585B2

公开(公告)日：2021-08-17

申请号：US16511798

申请日：2019-07-15

Applicant: PHILLIPS 66 COMPANY

Inventor： Kathy Woody ,  Laura Nielsen ,  Hualong Pan

IPC: C08G61/12 ,  H01L51/00 ,  C08L65/00 ,  H01L51/42

Abstract: A novel AB-type copolymer for use in organic photovoltaics. The AB-type copolymer comprises
a 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：US20210249605A1

公开(公告)日：2021-08-12

申请号：US17238450

申请日：2021-04-23

Applicant: PHILLIPS 66 COMPANY

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

IPC: H01L51/00 ,  C08G61/12

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：US20210238344A1

公开(公告)日：2021-08-05

申请号：US17238533

申请日：2021-04-23

Applicant: PHILLIPS 66 COMPANY

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

IPC: C08G61/12

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

公开(公告)号：US20210066608A1

公开(公告)日：2021-03-04

申请号：US17003007

申请日：2020-08-26

Applicant: PHILLIPS 66 COMPANY

Inventor： Hualong Pan ,  Kathy Woody

IPC: H01L51/00

Abstract: A polymer comprising: 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. 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. Additionally, R2 and R3 are independently selected from F, Cl, Br and I. 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 and wherein h+j is between 0.2 to 0.6 and i+k is between 0.4 and 0.8

公开(公告)号：US10787537B2

公开(公告)日：2020-09-29

申请号：US16253992

申请日：2019-01-22

Applicant: PHILLIPS 66 COMPANY

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

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

Abstract: A method of coupling and 5,5-Y-3,3′-difluoro-2,2′-bithiophene to produce wherein X can be any known compound capable of coupling with the Y-difluorothiophene and Y is selected from the group consisting of Br, a stannyl group, a boronic ester and a H.