# US 2021/0242406 A1 · Unsymmetrical benzothiadiazole-based random copolymers

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2021/0242406 A1
- Document ID: US20210242406A1
- Status: Published application
- Kind: A1
- Application number: 17/238,415
- Filed: 2021-04-23
- Published: 2021-08-05
- Earliest claimed: 2017-07-07
- Assignees: Phillips 66 Company
- Applicants: Phillips 66 Company
- Inventors: Hualong Pan; Kathy Woody; Brian Worfolk; Taeshik Earmme
- Web page: https://patentgrep.com/patent/US20210242406A1

## CPC

- C08G 61/123: {derived from five-membered heterocyclic compounds}
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/151: {Copolymers}
- C08G 2261/122: statistical
- C08G 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/1424: containing ether groups, including alkoxy
- C08G 2261/146: Side-chains containing halogens
- C08G 2261/149: Side-chains having heteroaromatic units
- C08G 2261/314: Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/3243: containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/414: Stille reactions
- C08G 2261/91: Photovoltaic applications
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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.

## Claims

### Claim 1

A random copolymer comprising monomer units A, B and C:
wherein A comprises
B comprises
and C comprises an aryl group
wherein:
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; and
X1 and X2 are identical and selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.

### Claim 2 (depends on 1)

The random copolymer of claim 1, wherein the molecular weight ranges from 1,000 to 100,000 kDa.

### Claim 3 (depends on 1)

The random copolymer of claim 1, wherein the aryl group of C is selected from the group consisting of:

### Claim 4 (depends on 1)

The random copolymer of claim 1, wherein C is 3,3′-difluoro-2,2′-bithiophene.

### Claim 5 (depends on 1)

The random copolymer of claim 1, wherein the molecular complex is used as photovoltaic material in one or more photovoltaic devices.

### Claim 6 (depends on 5)

The random copolymer of claim 5, wherein the one or more photovoltaic devices are polymer solar cell devices or photodetector devices.

### Claim 7 (depends on 1)

The random copolymer of claim 1, wherein the molecular complex is used as an active layer material in one or more electronic devices.

### Claim 8 (depends on 4)

The random copolymer of claim 4, wherein the one or more electronic devices are field effect transistors, light emitting devices and sensors, electrochromic devices and capacitors.

### Claim 9 (depends on 1)

The random copolymer of claim 1, wherein when used as a photovoltaic polymer produces a power conversion efficiency greater than 7.0%.

### Claim 10 (depends on 1)

The random copolymer of claim 1, wherein when used as a photovoltaic polymer produces a fill factor greater than 69%.

### Claim 11 (depends on 1)

The random copolymer of claim 1, wherein R1 and R2 are not identical.

### Claim 12 (depends on 1)

The random copolymer of claim 1 wherein A comprises
B comprises
and C comprises
wherein R3 and R3′ or R4 and R4′ are not equal.

### Claim 13 (depends on 1)

The random copolymer of claim 1, wherein the copolymer contains a unit ABC.

### Claim 14 (depends on 1)

The random copolymer of claim 1 wherein the copolymer contains a unit ACB.

### Claim 15 (depends on 1)

The random copolymer of claim 1, wherein the copolymer contains a unit BAC.

### Claim 16 (depends on 1)

The random copolymer of claim 1, wherein the copolymer contains a unit BCA.

### Claim 17 (depends on 1)

The random copolymer of claim 1, wherein the copolymer contains a unit CAB.

### Claim 18 (depends on 1)

The random copolymer of claim 1, wherein the copolymer contains a unit CBA.

### Claim 19

A random copolymer comprising monomer units A, B and C:
wherein A comprises
B comprises
and C comprises an aryl group
wherein:
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; and
X1 and X2 are F.