Conductive polymer, conductive polymer composition, conductive polymer organic film, and organic photoelectric device including the same

Patent metadata

Field	Value
Publication number	US-8932493-B2
Application number	US-201113169492-A
Country	US
Kind code	B2
Filing date	Jun 27, 2011
Priority date	Dec 26, 2008
Publication date	Jan 13, 2015
Grant date	Jan 13, 2015

Abstract

A conductive polymer, a conductive polymer composition, a conductive polymer organic film, and an organic photoelectric device including the same, the conductive polymer including repeating units represented by the following Chemical Formula 1, repeating units represented by the following Chemical Formula 2, and repeating units represented by the following Chemical Formula 3:

First claim

What is claimed is:

1. A conductive polymer comprising repeating units represented by the following Chemical Formula 1, repeating units represented by the following Chemical Formula 2, and repeating units represented by the following Chemical Formula 3:

wherein in the above Chemical Formulae 1 to 3,
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently one of hydrogen; a substituted or unsubstituted alkyl; a substituted or unsubstituted heteroalkyl; a substituted or unsubstituted alkoxy; a substituted or unsubstituted heteroalkoxy; a substituted or unsubstituted aryl; a substituted or unsubstituted arylalkyl; a substituted or unsubstituted aryloxy; a substituted or unsubstituted heteroaryl; a substituted or unsubstituted heteroarylalkyl; a substituted or unsubstituted heteroaryloxy; a substituted or unsubstituted cycloalkyl; a substituted or unsubstituted heterocycloalkyl; a substituted or unsubstituted alkylester; a substituted or unsubstituted heteroalkylester; a substituted or unsubstituted arylester; a substituted or unsubstituted heteroarylester, and a halogen,
A is one of a single bond; a substituted or unsubstituted alkylene; a substituted or unsubstituted heteroalkylene; a substituted or unsubstituted alkoxylene; a substituted or unsubstituted heteroalkoxylene; a substituted or unsubstituted arylene; a substituted or unsubstituted arylalkylene; a substituted or unsubstituted aryloxylene; a substituted or unsubstituted heteroarylene; a substituted or unsubstituted heteroarylalkylene; a substituted or unsubstituted heteroaryloxylene; a substituted or unsubstituted cycloalkylene; a substituted or unsubstituted heterocycloalkylene; a substituted or unsubstituted alkylene ester; a substituted or unsubstituted heteroalkylene ester; a substituted or unsubstituted arylene ester; and a substituted or unsubstituted heteroarylene ester,
B is an ion-pair of a cation and an anion, the cation being selected from the group of H + , a metal ion selected from the group of Na + , K + , Li + , Mg 2+ , Zn 2+ , and Al 3+ , NR 3 + where R is H or a substituted or unsubstituted alkyl, and an organic ion of CH 3 (—CH 2 —) p O + where p ranges from 1 to 50, and the anion being selected from the group of PO 3 2− , SO 3 − , COO − , I − , and CH 3 COO − ,
C is one of a single bond; —O—; —S—; —NH—; a substituted or unsubstituted alkylene; a substituted or unsubstituted heteroalkylene; a substituted or unsubstituted arylene; a substituted or unsubstituted oxyalkylene; a substituted or unsubstituted hetero-oxyalkylene; a substituted or unsubstituted arylalkylene; a substituted or unsubstituted aryloxylene; a substituted or unsubstituted aryleneamine; a substituted or unsubstituted pyrrolene; a substituted or unsubstituted thiophenylene; a substituted or unsubstituted heteroarylene; a substituted or unsubstituted heteroarylalkylene; a substituted or unsubstituted heteroaryloxylene; a substituted or unsubstituted cycloalkylene; a substituted or unsubstituted heterocycloalkylene; a substituted or unsubstituted alkylene ester; a substituted or unsubstituted heteroalkylene ester; a substituted or unsubstituted arylene ester; and a substituted or unsubstituted heteroarylene ester,
D is one of a substituted or unsubstituted polyphenylene, a substituted or unsubstituted polyphenylenevinylene, a polyaniline or a derivative thereof represented by the following Chemical Formula 4, a polypyrrole or a derivative thereof represented by the following Chemical Formula 5, a substituted or unsubstituted polythiophene or a derivative thereof, and a polymer of a cyclic monomer represented by the following Chemical Formula 6, and
E is a halogen-substituted carbon compound group that is unsubstituted or substituted with a heteroatom of nitrogen, phosphorus, sulfur, silicon, or oxygen,
wherein:
a number average molecular weight Mn of the polyaniline or derivative thereof represented by the following Chemical Formula 4 is about 2,000 to about 100,000, and a weight average molecular weight Mw of the polyaniline or derivative thereof represented by the following Chemical Formula 4 is about 3,000 to about 200,000,
a Mn of the polypyrrole or derivative thereof represented by the following Chemical Formula 5 is about 2,000 to about 100,000, and a Mw of the polypyrrole or a derivative thereof represented by the following Chemical Formula 5 is about 3,000 to about 200,000, and
a Mn of the polymer of a cyclic monomer represented by the following Chemical Formula 6 is about 2,000 to about 100,000, and a Mw of the polymer of a cyclic monomer represented by the following Chemical Formula 6 is about 3,000 to about 200,000,

wherein in the above Chemical Formula 4,
R a , R b , R c , and R d are each independently one of hydrogen; a substituted or unsubstituted C1-C30 alkyl; a substituted or unsubstituted C1-C30 heteroalkyl; a substituted or unsubstituted C1-C30 alkoxy; a substituted or unsubstituted C1-C30 heteroalkoxy; a substituted or unsubstituted C6-C30 aryl; a substituted or unsubstituted C6-C30 arylalkyl; a substituted or unsubstituted C6-C30 aryloxy; a substituted or unsubstituted C6-C30 arylamine; a substituted or unsubstituted C6-C30 pyrrole; a substituted or unsubstituted C6-C30 thiophene; a substituted or unsubstituted C2-C30 heteroaryl; a substituted or unsubstituted C2-C30 heteroarylalkyl; a substituted or unsubstituted C2-C30 heteroaryloxy; a substituted or unsubstituted C5-C20 cycloalkyl;
a substituted or unsubstituted C2-C30 heterocycloalkyl; a substituted or unsubstituted C2-C30 alkylester; a substituted or unsubstituted C1-C30 heteroalkylester; a substituted or unsubstituted C6-C30 arylester; and a substituted or unsubstituted C2-C30 heteroarylester,

wherein in the above Chemical Formula 5,
X is one of —NH—, —NR—; —PH, —PR—; —O—; and —S—, where R is a C1-C20 alkyl or a C6-C20 aryl, and
R e and R f are each independently one of —NH 2 , —NRR′; —PH 2 , —PRR′; —OH, —OR; —SH, —SR, wherein R and R′ are each independently hydrogen, a C1-C20 alkyl, or a C6-C20 aryl; a C1-C30 alkyl; a C6-C30 aryl; a C1-C30 alkoxy; a C1-C30 heteroalkyl; a C1-C30 heteroalkoxy; a C6-C30 arylalkyl; a C6-C30 aryloxy; a C6-C30 arylamine; a C6-C30 pyrrole; a C6-C30 thiophene; a C2-C30 heteroaryl; a C2-C30 heteroarylalkyl; a C2-C30 heteroaryloxy; a C5-C20 cycloalkyl; a C2-C30 heterocycloalkyl; a C2-C30 alkylester; a C1-C30 heteroalkylester; a C6-C30 arylester; a C2-C30 heteroarylester, or a combination thereof,

wherein in the above Chemical Formula 6,
X and Y are each independently one of —NH—, —NR—; —PH—, —PR—; —O—; and —S—, where R is a C1-C20 alkyl or a C6-C20 aryl,
Z is —(CR 1 R 2 ) x —CR 3 R 4 —(CR 5 R 6 ) y — wherein R 1 to R 6 are each independently one of —H, a C1-C20 alkyl, a C6-C14 aryl, and —CH 2 —ORi wherein Ri is —H, a C1-C6 alkyl acid group, a C2-C6 alkylester group, a C1-C6 heteroalkyl acid group, or a C1-C6 alkylsulfonic acid group, and
x and y are each independently integers of 0 to 5, and
wherein, in the above Chemical Formulae 4 to 6, one of the “*”is a portion bound with the C of Chemical Formula 2 and another “*” is —H or a substituted or unsubstituted C1-C30 alkyl.

2. The conductive polymer as claimed in claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently one of a substituted or unsubstituted C1-C30 alkyl; a substitute

Assignees

• Huh Dal-Ho
• Lee Jeong-Woo
• Min Soo-Hyun
• Chae Mi-Young
• Lee Tae-Woo
• Cheil Ind Inc

Inventors

• Huh Dal-Ho
• Lee Jeong-Woo
• Min Soo-Hyun
• Chae Mi-Young
• Lee Tae-Woo

Classifications

• C08G61/10

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C08L65/02

  Polyphenylenes · CPC title

• C08F212/32

  containing two or more rings · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• H01L51/004

  Electricity · mapped topic