# US 10,312,445 B2 · Polymer and organic electronic element comprising same

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- Number: US 10,312,445 B2
- Document ID: US10312445B2
- Status: Granted
- Kind: B2
- Application number: 15/562,116
- Filed: 2016-05-24
- Published: 2018-03-22
- Granted: 2019-06-04
- Earliest claimed: 2015-06-03
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Bogyu Lim; Jaechol Lee; Doowhan Choi; Sungkyoung Kang
- Web page: https://patentgrep.com/patent/US10312445B2

## CPC

- C08G 61/123: {derived from five-membered heterocyclic compounds}
- C08G 61/124: {with a five-membered ring containing one nitrogen atom in the ring}
- 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 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/146: Side-chains containing halogens
- C08G 2261/149: Side-chains having heteroaromatic units
- 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 2261/3243: containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/344: containing heteroatoms
- C08G 2261/364: containing hetero atoms
- C08G 2261/51: Charge transport
- C08G 2261/91: Photovoltaic applications
- C08G 2261/92: TFT applications
- C08G 2261/95: Use in organic luminescent diodes
- H10K 10/484: {characterised by the channel regions}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- 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

The present specification relates to a polymer, which comprises an electron acceptor functional group on a side chain and is represented by chemical formula 1 below, and to an organic electronic element comprising the same.

## Claims

### Claim 1

A polymer comprising a unit represented by the following Chemical Formula 1:
in Chemical Formula 1,
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,
R and R′ 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,
[Push] is a structure in which one or two or more among the following structures are bonded,
in the structures,
a is an integer from 1 to 4,
b and b′ are each an integer from 1 to 3,
when a, b, and b′ are each 2 or more, two or more structures in the parenthesis are the same as or different from each other,
X10 to X22 are the same as or different from each other, and are each independently CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se, or Te,
Y10 and Y11 are the same as or different from each other, and are each independently CRc, N, SiRc, P, or GeRc,
Ra, Rb, Rc, and R100 to R113 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,
[Pull1] and [Pull2] are a group that acts as an electron acceptor, are the same as or different from each other, and are each independently represented by the following Chemical Formula 2 or the following Chemical Formula 3,
in Chemical Formulae 2 and 3,
X3 to X7 are the same as or different from each other, and are each independently CR15R16, NR15, O, SiR15R16, PR15, S, GeR15R16, Se, or Te,
Y1 to Y4 are the same as or different from each other, and are each independently CR17, N, SiR17, P, or GeR17,
n1 is an integer of 0 or 1,
n2 to n4 are each an integer from 0 to 3,
when n2 to n4 are each an integer of 2 or more, two or more structures in the parenthesis are the same as or different from each other, and
R1 to R17 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.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein X1 and X2 are S.

### Claim 3 (depends on 1)

The polymer of claim 1, wherein the [Pull1] and the [Pull2] represented by Chemical Formula 2 or Chemical Formula 3 are represented by the following Chemical Formula 2-1 or Chemical Formula 3-1:
in Chemical Formulae 2-1 and 3-1,
n1 to n4 and R1 to R14 are the same as those defined in Chemical Formula 2 and Chemical Formula 3.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein the polymer comprises a unit represented by any one of the following Chemical Formulae 1-1 to 1-4:
in Chemical Formulae 1-1 to 1-4,
a is an integer from 1 to 4,
n is a repeating number of the unit, and an integer from 1 to 1,000,
n1 and n1′ are an integer of 0 or 1,
n2 to n4 and n2′ to n4′ are each an integer from 0 to 3,
when a, n2 to n4, and n2′ to n4′ are each an integer of 2 or more, two or more structures in the parenthesis are the same as or different from each other, and
R1 to R14, R1′ to R14′, R104, R105, R112, and R113 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.

### Claim 5 (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 6 (depends on 1)

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

### Claim 7 (depends on 1)

An organic electronic device comprising:
a first electrode;
a second electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise the polymer according to claim 1.

### Claim 8 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is selected from the group consisting of an organic light emitting device; an organic solar cell; and an organic transistor.

### Claim 9 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is an organic solar cell comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, which comprises a photoactive layer disposed between the first electrode and the second electrode, and
one or more layers of the organic material layer comprise the polymer.

### Claim 10 (depends on 9)

The organic electronic device 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 polymer.

### Claim 11 (depends on 9)

The organic electronic device of claim 9, wherein the photoactive layer has a bulk heterojunction structure comprising an electron-donating material and an electron-accepting material, and the electron-donating material comprises the polymer.

### Claim 12 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is an organic transistor comprising: a source; a drain; a gate; and an organic material layer having one or more layers, and one or more layers of the organic material layer comprise the polymer.