# US 2018/0026200 A1 · Heterocyclic compound and organic solar cell comprising same

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- Number: US 2018/0026200 A1
- Document ID: US20180026200A1
- Status: Published application
- Kind: A1
- Application number: 15/547,310
- Filed: 2016-02-17
- Published: 2018-01-25
- Earliest claimed: 2015-02-17
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Junghyun PARK; Hang Ken LEE; Donggu LEE; Jaesoon BAE; Jaechol LEE
- Web page: https://patentgrep.com/patent/US20180026200A1

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D 409/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 495/04: Ortho-condensed systems
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- 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 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

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

## Claims

### Claim 1

A heterocyclic compound represented by the following Chemical Formula 1:
in Chemical Formula 1,
m1, m2, n1, and n2 are each an integer from 1 to 3,
when m1, m2, n1, and n2 are each 2 or more, two or more structures in the square bracket are the same as or different from each other,
L1, L2, and L3 are the same as or different from each other, and are each independently a direct bond; or a divalent linking group,
X1 to X10 are the same as or different from each other, and are each independently CRR′, NR, O, SiRR′, PR, S, GeRR′, Se, or Te,
R, R′, R1 to R12, and R21 to R28 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group comprising one or more of N, O, and S atoms, and
A1 and A2 are the same as or different from each other, and are each independently a structure which acts as an electron acceptor.

### Claim 2 (depends on 1)

The heterocyclic compound of claim 1, wherein L1, L2, and L3 are the same as or different from each other, and each independently comprise one or more selected from the group consisting of a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; and a substituted or unsubstituted divalent heterocyclic group comprising one or more of N, O, S, Si, and Ge.

### Claim 3 (depends on 1)

The heterocyclic compound of claim 1, wherein L1 is selected from a direct bond; or the following structures:
in the structures,
U1 is NR111, S, or O,
U2 and U3 are the same as or different from each other, and are each independently N or CH,
R101 to R111 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group comprising one or more of N, O, and S atoms,
r101, r106, and r110 are each 1 or 2,
r103 is an integer from 1 to 4,
r108 and r109 are each an integer from 1 to 3,
n110 is an integer of 1 or more, and
when r101, r103, r106, r108, r109, r110, and n110 are each present in a plural number, a plurality of structures in the parenthesis is the same as or different from each other.

### Claim 4 (depends on 1)

The heterocyclic compound of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently any one of the following structures:
in the structures,
a is an integer from 1 to 7,
b and c are each an integer from 1 to 4,
when a is 2 or more, two or more R15's are the same as or different from each other,
when b is 2 or more, two or more R16's are the same as or different from each other,
when c is 2 or more, two or more R17's are the same as or different from each other, and
R14 to R20 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group comprising one or more of N, O, and S atoms.

### Claim 5 (depends on 1)

The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by the following Chemical Formula 1-1:
in Chemical Formula 1-1,
the definitions of m1, m2, n1, n2, L1, L2, L3, R1 to R12, R21 to R28, A1, and A2 are the same as those of Chemical Formula 1.

### Claim 6 (depends on 1)

The heterocyclic compound of claim 1, wherein R1 to R12 and R21 to R28 are the same as or different from each other, and are each independently hydrogen;
or a substituted or unsubstituted alkyl group.

### Claim 7 (depends on 1)

The heterocyclic compound of claim 1, wherein A1 and A2 are the same as or different from each other, and are each independently
and
R14 is a substituted or unsubstituted alkyl group.

### Claim 8 (depends on 1)

The heterocyclic compound of claim 1, wherein Chemical Formula 1 is represented by any one of the following Compounds 1-1 to 1-13:
in Compounds 1-2, 1-4 to 1-9, 1-11, and 1-12,
n110 is an integer of 1 or more, and
R201 to R217 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group comprising one or more of N, O, and S atoms.

### Claim 9 (depends on 1)

An organic solar cell comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode and comprising a photoactive layer,
wherein one or more layers of the organic material layer comprise the heterocyclic compound according claim 1.

### Claim 10 (depends on 9)

The organic solar cell of claim 9, wherein the organic material layer comprises a hole transporting layer, a hole injection layer, or a layer which simultaneously transports and injects holes, and
the hole transporting layer, the hole injection layer, or the layer which simultaneously transports and injects holes comprises the heterocyclic compound.

### Claim 11 (depends on 9)

The organic solar cell of claim 9, wherein the organic material layer comprises an electron injection layer, an electron transporting layer, or a layer which simultaneously injects and transports electrons, and
the electron injection layer, the electron transporting layer, or the layer which simultaneously injects and transports electrons comprises the heterocyclic compound.

### Claim 12 (depends on 9)

The organic solar cell of claim 9, wherein the photoactive layer comprises one or two or more selected from the group consisting of an electron donor and an electron acceptor, and the electron donor comprises the heterocyclic compound.

### Claim 13 (depends on 12)

The organic solar cell of claim 12, wherein the electron donor and the electron acceptor constitute a bulk heterojunction (BHJ).

### Claim 14 (depends on 9)

The organic solar cell of claim 9, 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 the p-type organic material layer comprises the heterocyclic compound.