# US 2019/0378987 A1 · Polymer and organic solar cell comprising same

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

- Number: US 2019/0378987 A1
- Document ID: US20190378987A1
- Status: Published application
- Kind: A1
- Application number: 16/339,665
- Filed: 2017-12-13
- Published: 2019-12-12
- Earliest claimed: 2017-03-06
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Ji Hoon KIM; Doowhan CHOI; Songrim JANG; Bogyu LIM
- Web page: https://patentgrep.com/patent/US20190378987A1

## 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 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- 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 2261/18: conjugated
- C08G 2261/228: Polymers, i.e. more than 10 repeat units
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/364: containing hetero atoms
- C08G 2261/414: Stille reactions
- C08G 2261/91: Photovoltaic applications
- H10K 30/152: {the wide bandgap semiconductor comprising zinc oxide, e.g. ZnO}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 85/215: {comprising substituents, e.g. PCBM}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- 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
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present specification relates to a polymer and an organic solar cell including the same.

## Claims

### Claim 1

A polymer comprising:
a first unit of Chemical Formula 1; and
a second unit of Chemical Formula 2:
wherein:
d1, d2, x, and x′ are each 1 or 2;
when d1, d2, x, and x′ are each 2, structures in the parenthesis are the same as or different from each other;
X1 and X2 are the same as or different from each other, and are each independently CRR, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
Y1 to Y4 are the same as or different from each other, and are each independently CR″, N, SiR″, P, or GeR″;
X and X′ are the same as or different from each other, and are each independently S or Se;
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted straight or branched alkyl group;
R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted branched alkyl group;
G1 and G2 are the same as or different from each other, and are each independently hydrogen, or fluorine;
R, R′, and R″ are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
D1 and D2 are the same as or different from each other, and are each independently any one selected from the following structures,
wherein:
X″, X′″, and X″″ are the same as or different from each other, and are each independently S or Se;
Y and Y′ are the same as or different from each other, and are each independently CR′″, N, SiR′″, P, or Ge R′″;
G11 to G18, G101, and G102 are the same as or different from each other, and are each independently hydrogen, or fluorine;
R′″ is hydrogen, deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
g is 0 or 1.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein Chemical Formula 1 is Chemical Formula 1-1:
wherein Ar1, Ar2, and D1 are the same as those defined in Chemical Formula 1.

### Claim 3 (depends on 1)

The polymer of claim 1, wherein Chemical Formula 2 is Chemical Formula 2-1:
wherein R1, R2, G1, G2, and D2 are the same as those defined in Chemical Formula 2.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein Chemical Formula 1 is any one of Chemical Formulae 1-2 to 1-5:
wherein:
Ar1 and Ar2 are the same as those defined in Chemical Formula 1;
G11 to G18, G101, and G102 are the same as or different from each other, and are each independently hydrogen, or fluorine; and
R′″ is hydrogen, deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

### Claim 5 (depends on 1)

The polymer of claim 1, wherein Chemical Formula 2 is any one of Chemical Formulae 2-2 to 2-5:
wherein:
R1, R2, G1, and G2 are the same as those defined in Chemical Formula 2;
G11 to G18, G101, and G102 are the same as or different from each other, and are each independently hydrogen, or fluorine; and
R′″ is hydrogen, deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

### Claim 6 (depends on 1)

The polymer of claim 1, wherein the polymer comprises a unit of Chemical Formula 4 or 5:
wherein:
A is Chemical Formula 1;
B is Chemical Formula 2;
l is a mole fraction and 0<l<1;
m is a mole fraction and 0<m<1;
l+m=1; and
n is a repeating number of the unit, and is an integer of from 1 to 10,000.

### Claim 7 (depends on 1)

The polymer of claim 1, wherein the polymer comprises a unit of any one of Chemical Formulae 4-1 to 4-16 and 5-1 to 5-16:
wherein:
Ar1 and Ar2 are the same as those defined in Chemical Formula 12;
R1, R2, G1, and G2 are the same as those defined in Chemical Formula 2;
G11 to G18, G101, and G102 are the same as or different from each other, and are each independently hydrogen, or fluorine;
R′″ is hydrogen, deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
l is a mole fraction and 0<l<1;
m is a mole fraction and 0<m<1;
l+m=1; and
n is a repeating number of the unit, and is an integer of from 1 to 10,000.

### Claim 8 (depends on 1)

The polymer of claim 1, wherein the polymer comprises a unit of any one of Chemical Formulae 5-1-1, 5-5-1, 5-11-1, and 5-16-1:
wherein:
l is a mole fraction and 0<l<1;
m is a mole fraction and 0<m<1;
l+m=1; and
n is a repeating number of the unit, and is an integer of from 1 to 10,000.

### Claim 9 (depends on 1)

The polymer of claim 1, wherein the polymer has a HOMO energy level of 5 eV to 5.9 eV.

### Claim 10 (depends on 1)

The polymer of claim 1, wherein the polymer has a number average molecular weight of 5,000 g/mol to 1,000,000 g/mol.

### Claim 11 (depends on 1)

The polymer of claim 1, wherein the polymer has a molecular weight distribution of 1 to 10.

### Claim 12 (depends on 1)

An organic solar cell comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic material layer between the first electrode and the second electrode, the organic material layer comprising one or more layers and comprising a photoactive layer,
wherein the one or more layers of the organic material layer comprise the polymer of claim 1.

### Claim 13 (depends on 1, 12)

The organic solar cell of claim 12, wherein the photoactive layer comprises one or more selected from the group consisting of an electron donor and an electron acceptor, and
wherein the electron donor comprises the polymer of claim 1.

### Claim 14 (depends on 13)

The organic solar cell of claim 13, wherein the electron donor and the electron acceptor are both present and constitute a bulk heterojunction (BHJ).

### Claim 15 (depends on 13)

The organic solar cell of claim 13, wherein the photoactive layer further comprises an additive.

### Claim 16 (depends on 1, 12)

The organic solar cell of claim 12, wherein the photoactive layer has a bilayer thin film structure comprising an n-type organic material layer and a p-type organic material layer, and
wherein the p-type organic material layer comprises the polymer of claim 1.

### Claim 17 (depends on 15)

The organic solar cell of claim 15, wherein the additive comprises one or two additives selected from the group consisting of 1,8-diiodooctane (DIO), 1-chloronaphthalene (1-CN), diphenylether (DPE), octane dithiol, and tetrabromothiophene.

### Claim 18 (depends on 15)

The organic solar cell of claim 15, wherein the additive comprises an organic material having a boiling point of 30° C. to 300° C.

### Claim 19 (depends on 1)

The polymer of claim 1, wherein the polymer has a number average molecular weight of 100,000 g/mol or less.

### Claim 20 (depends on 1)

The polymer of claim 1, wherein the polymer has a molecular weight distribution of 1 to 3.