# US 10,312,446 B2 · Conductive polymers, the organic photovoltaic cell comprising the same, and the synthesis thereof

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- Number: US 10,312,446 B2
- Document ID: US10312446B2
- Status: Granted
- Kind: B2
- Application number: 15/637,023
- Filed: 2017-06-29
- Published: 2018-01-04
- Granted: 2019-06-04
- Earliest claimed: 2016-06-30
- Assignees: Daegu Gyeongbuk Institute of Science and Technology
- Applicants: Daegu Gyeongbuk Institute of Science and Technology
- Inventors: Youn Gu Lee; Hong Gi Kim
- Web page: https://patentgrep.com/patent/US10312446B2

## CPC

- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- H10K 85/151: {Copolymers}
- H10K 85/211: {Fullerenes, e.g. C60}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- H10K 30/152: {the wide bandgap semiconductor comprising zinc oxide, e.g. ZnO}
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 30/50: Photovoltaic [PV] devices
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to a conductive polymer, the organic photovoltaic cell comprising the same, and the synthesis method of the same. The novel polymer, according to the present invention, displays more excellent optical properties and higher photoelectric conversion efficiency than the conventional RRa (regiorandom) polymer due to its symmetrical structure of quaterthiophene and benzothiadiazole substituted with fluorine.

## Claims

### Claim 1

A method for preparing the polymer represented by formula 1, which comprises the following steps:
(a) producing the compound represented by formula 2 having a symmetrical structure by reacting a quaterthiophene derivative and a benzothiadiazole derivative with the substitution of bromine and fluorine in the presence of a palladium catalyst;
(b) producing the compound represented by formula 3 by reacting the compound represented by formula 2 with a brominating agent; and
(c) reacting the compound represented by formula 3 with a bithiophene derivative in the presence of a palladium catalyst:
wherein R is independently C1˜C30 straight or branched alkyl, C1˜C30 straight or branched alkoxy, or C6˜C30 aryl, wherein the alkyl, alkoxy, and aryl can be substituted with one or more C1˜C10 alkyl, hydroxyl, amino, or carboxy, and the alkyl, alkoxy, and aryl can independently contain one or more hetero atoms,
X is independently H or F,
N is an integer of 1˜500.

### Claim 2 (depends on 1)

The method for preparing the polymer represented by formula 1 according to claim 1, wherein the R in the formulas above is independently selected from the group consisting of ethylhexyl, butyloctyl, hexyldecyl, and octyldodecyl.

### Claim 3 (depends on 1)

The method for preparing the polymer represented by formula 1 according to claim 1, wherein the palladium catalyst is selected from the group consisting of PdCl2, Pd(OAc)2, Pd(CH3CN)2Cl2, Pd(PhCN)2Cl2, Pd2(dba)3, and Pd(PPh3)4.

### Claim 4 (depends on 1)

The method for preparing the polymer represented by formula 1 according to claim 1, wherein the quaterthiophene derivative is (3,3′″-bis(2-octyldodecyl)-[2,2′:5′,2″:5″,2″-quaterthiophene]-5,5′″-yl)bis(trimethylstannane) or (3″,4′-difluoro-3,3′″-bis(2-octyldodecyl)-[2,2′:5′,2″: 5″,2′″-quaterthiophene]-5,5′″-diyl)bis(trimethylstannane).

### Claim 5 (depends on 1)

The method for preparing the polymer represented by formula 1 according to claim 1, wherein the benzothiadiazole derivative with the substitution of bromine and fluorine is 4-bromo-5-fluoro-7-(4-(2-octyldodecyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole.

### Claim 6 (depends on 1)

The method for preparing the polymer represented by formula 1 according to claim 1, wherein the bithiophene derivative is 5,5′-bis(trimethylstannyl)-2,2′-bithiophene or (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethyl stannane).