Copolymer and organic solar cell including same

Patent metadata

Field	Value
Publication number	US-11225549-B2
Application number	US-201816481656-A
Country	US
Kind code	B2
Filing date	Jun 22, 2018
Priority date	Jul 6, 2017
Publication date	Jan 18, 2022
Grant date	Jan 18, 2022

Abstract

The present specification provides a copolymer including: a repeating unit derived from a compound represented by Formula 1; a first conjugated monomer; and a second conjugated monomer different from the first conjugated monomer, and an organic solar cell including the same.

First claim

The invention claimed is:

1. A copolymer comprising:
a repeating unit derived from a compound represented by the following Formula 1-2:

in Formula 1-2,
m1, m2, m1′, and m2′ are the same as or different from each other, and are each independently an integer from 1 to 5,
when m1, m2, m1′and m2′ are each 2 or more, each of

is the same as or different from each other,
q1, q2, q1′, and q2′ are the same as or different from each other, and are each independently an integer from 1 to 5,
when q1, q2, and q1′, and q2′ are each 2 or more, each of

is the same as or different from each other,
X1, X2, X1′, X2′, Z1 to Z5, and Z1′to Z5′ are the same as or different from each other, and are each independently S, O, Se, Te, NR, CRR′, SiRR′, PR, or GeRR′,
R a , R b , R c , R, R′, R1 to R4, and R11 to R18 are the same as or different from each other, and
E1 is a first conjugated monomer,
E2 is a second conjugated monomer different from the first conjugated monomer,
R1, R4, R1′, and R4′ are the same as or different from each other, and are each independently deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide 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 amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R, R′, R11 to R18, and R11′ to R18′ are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group;
a carbonyl group; an ester group; an imide group; an amide 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 amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R51, R51′, R52, and R52′ are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group;
f is a mole fraction, and a real number of 0 <f<1,
g is a mole fraction, and a real number of 0 <g<1,
f+g=1, and
n is the number of repeating units of the unit, and an integer from 1 to 10,000.

2. The copolymer of claim 1 , wherein the first conjugated monomer and the second conjugated monomer each independently comprise one group of or a combination of two or more groups of a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted divalent heterocyclic group.

3. The copolymer of claim 1 , wherein the first conjugated monomer and the second conjugated monomer each independently comprise any one of or a combination of two or more of the following structures:

in the structures,
a, a′, b, and b′ are each an integer from 1 to 5,
when a, a′, b, and b′ are each 2 or more, each of R113, R114, R115 and R116 is the same as or different from each other,
X11 to X30 and X33 to X40 are the same as or different from each other, and are each independently S, O, Se, Te, NR d , CR d R e , SiR d R e , PR d , or GeR d R e ,
X31 and X32 are the same as or different from each other, and are each independently C, Si, or Ge, and
R101 to R124, R d , and R e are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide 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 amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

4. The copolymer of claim 1 , wherein R11 to R18 are the same as or different from each other, and are each independently hydrogen; a halogen group; or a substituted or unsubstituted alkoxy group.

5. The copolymer of claim 1 , wherein X1, X2, and Z1 to Z5 are each S.

6. The copolymer of claim 1 , wherein the first conjugated monomer and the second conjugated monomer each independently comprise any one of or a combination of two or more of the following structures:

in the structures,
X11 to X14, X19, X20, X33 to X40, X11′, and X11″ are the same as or different from each other, and are each independently S, O, Se, Te, NR d , CR d R e , SiR d R e , PR d , or GeR d R e , and
R101 to R110, R117 to R124, R101′, R101″, R102′, R102″, R d , and R e are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide 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 amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubs

Assignees

• Lg Chemical Ltd

Inventors

• Lim Bogyu
• Kim Ji Hoon
• Jang Songrim
• Choi Doowhan

Classifications

• C08G2261/3246

  containing nitrogen and sulfur as heteroatoms · CPC title

• H10K30/84

  Layers having high charge carrier mobility · CPC title

• H10K85/151

  Copolymers · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title