Conductive organic semiconductor compound, method for preparing the same and organic thin-film transistor including the same

Patent metadata

Field	Value
Publication number	US-9941476-B2
Application number	US-201514659809-A
Country	US
Kind code	B2
Filing date	Mar 17, 2015
Priority date	Nov 21, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The present disclosure provides an organic semiconductor compound, which has superior charge mobility, low band gap, wide light absorption area and adequate molecular energy level. The conductive organic semiconductor compound of the present disclosure can be used as a material for various organic optoelectric devices such as an organic photodiode (OPD), an organic light-emitting diode (OLED), an organic thin-film transistor (OTFT), an organic solar cell, etc. In addition, it can be prepared into a thin film via a solution process, can be advantageously used to fabricate large-area devices and can reduce the cost of device fabrication.

First claim

What is claimed is:

1. A conductive organic semiconductor compound represented by [Chemical Formula I] or [Chemical Formula II]:

wherein Ar is selected from [Structural Formula 1] and n is an integer from 5 to 100,000:

wherein
each of R 1 and R 2 , which are identical or different, is independently selected from a group consisting of hydrogen, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amide group, an ester group, a ketone group, a thioester group, a silyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group containing at least one of S, N, O, P and Si, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 5 -C 50 aryl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 50 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylamino group, a substituted or unsubstituted C 6 -C 30 arylamino group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group and a substituted or unsubstituted C 5 -C 50 arylsilyl group.

2. The conductive organic semiconductor compound according to claim 1 , wherein [Chemical Formula II] is represented by [Chemical Formula III] or [Chemical Formula IV]:

wherein
each of R 3 and R 4 , which are identical or different, is independently selected from a group consisting of hydrogen, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amide group, an ester group, a ketone group, a thioester group, a silyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group containing at least one of S, N, O, P and Si, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 5 -C 50 aryl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 50 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylamino group, a substituted or unsubstituted C 6 -C 30 arylamino group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group and a substituted or unsubstituted C 5 -C 50 arylsilyl group, and
n is an integer from 5 to 100,000.

3. The conductive organic semiconductor compound according to claim 2 , wherein [Chemical Formula III] is represented by [Chemical Formula V]:

wherein n is an integer from 5 to 100,000.

4. The conductive organic semiconductor compound according to claim 2 , wherein [Chemical Formula IV] is represented by [Chemical Formula VI]:

wherein n is an integer from 5 to 100,000.

5. The conductive organic semiconductor compound according to claim 1 , wherein the conductive organic semiconductor compound has an electron mobility of 1×10 −6 cm 2 /N·s or higher.

6. The conductive organic semiconductor compound according to claim 1 , wherein the conductive organic semiconductor compound has a band gap of 1.0-3.0 eV.

7. An organic semiconductor thin film comprising one or more conductive organic semiconductor compound,
wherein the conductive organic semiconductor compound is represented by [Chemical Formula I] or [Chemical Formula II]:

wherein Ar is selected from [Structural Formula 1] and n is an integer from 5 to 100,000:

wherein
each of R 1 and R 2 , which are identical or different, is independently selected from a group consisting of hydrogen, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amide group, an ester group, a ketone group, a thioester group, a silyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group containing at least one of S, N, O, P and Si, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 5 -C 50 aryl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 50 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkylamino group, a substituted or unsubstituted C 6 -C 30 arylamino group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group and a substituted or unsubstituted C 5 -C 50 arylsilyl group.

8. An organic thin-film transistor, comprising:
a substrate;
a gate electrode formed on the substrate;
an insulating layer formed on the gate electrode;
an organic semiconductor thin film formed on the insulating layer; and
a source electrode layer and a drain electrode layer formed on the organic semiconductor thin film,
wherein the organic semiconductor thin film includes one or more conductive organic semiconductor compound,
wherein the conductive organic semiconductor compound is
represented by [Chemical Formula I] or [Chemical Formula II]:

wherein Ar is selected from [Structural Formula 1] and n is an integer from 5 to 100,000:

wherein
each of R 1 and R 2 , which are identical or different, is independently selected from a group consisting of hydrogen, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amide group, an ester group, a ketone group, a thioester group, a silyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C

Assignees

• Korea Inst Sci & Tech

Inventors

• Son Hae Jung
• Ko Min Jae
• Kim Bong Soo
• Lee Doh-Kwon
• Kim Jin Young
• Kim Hong Gon
• Park Sungmin

Classifications

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title

• C08G2261/146

  Side-chains containing halogens · CPC title

• C08G2261/364

  containing hetero atoms · CPC title

• C08G61/123 Primary

  derived from five-membered heterocyclic compounds · CPC title

• C08G2261/18

  conjugated · CPC title