Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film

Patent metadata

Field	Value
Publication number	US-9537102-B2
Application number	US-201313910246-A
Country	US
Kind code	B2
Filing date	Jun 5, 2013
Priority date	Jun 5, 2012
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

A low-molecular-weight fused polycyclic heteroaromatic compound may have a compact planar structure in which seven or more rings are fused together, and thereby exhibits high charge mobility, and furthermore, enables the use of a deposition process or a room-temperature solution process when applied to devices, therefore realizing improved processibility. An organic thin film and electronic device may include the fused polycyclic heteroaromatic compound.

First claim

What is claimed is:

1. A fused polycyclic heteroaromatic compound comprising a structural unit represented by the following Chemical Formula 1:

wherein, in the above Chemical Formula 1,
Ar is one of a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, and a substituted or unsubstituted anthracene,
each of X 1 to X 4 are independently one of O, S, Se, Te, N—R a , and CR b , wherein each of R a and R b are independently one of hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, —OR 11 , wherein R 11 is a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 4 to C 30 cycloalkyl group, —OR 12 , wherein R 12 is a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, —C(═O)R 13 , wherein R 13 is a substituted or unsubstituted C 1 to C 30 alkyl group, —S(═O) 2 R 14 , wherein R 14 is a substituted or unsubstituted C 1 to C 30 alkyl group, and —NHC(═O)OR 15 , wherein R 15 is a substituted or unsubstituted C 1 to C 30 alkyl group,
at least one of X 1 and X 2 is selected from O, S, Se, and Te,
at least one of X 3 and X 4 is selected from O, S, Se, and Te,
each of X 5 and X 6 are independently one of O, S, Se, Te, and CR b R c wherein each of R b to R c are independently one of hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, —OR 11 , wherein R 11 is a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 4 to C 30 cycloalkyl group, —OR 12 , wherein R 12 is a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, —C(═O)R 13 , wherein R 13 is a substituted or unsubstituted C 1 to C 30 alkyl group, —S(═O) 2 R 14 , wherein R 14 is a substituted or unsubstituted C 1 to C 30 alkyl group, and —NHC(═O)OR 15 , wherein R 15 is a substituted or unsubstituted C 1 to C 30 alkyl group, and
each of R 1 to R 6 are independently one of hydrogen, —F, —Cl, —Br, —I, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkenyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group.

2. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound is represented by the following Chemical Formula 1A:

wherein, in the above Chemical Formula 1A,
each of X 1 to X 4 are independently one of O, S, Se, Te, N—R a , and CR b , wherein each of R a and R b are independently one of hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, —OR 11 , wherein R 11 is a substituted or unsubstituted C 6 to C 30 aryl group), a substituted or unsubstituted C 4 to C 30 cycloalkyl group, —OR 12 , wherein R 12 is a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, —C(═O)R 13 , wherein R 13 is a substituted or unsubstituted C 1 to C 30 alkyl group, —S(═O) 2 R 14 , wherein R 14 is a substituted or unsubstituted C 1 to C 30 alkyl group, and —NHC(═O)OR 15 , wherein R 15 is a substituted or unsubstituted C 1 to C 30 alkyl group,
at least one of X 1 and X 2 is selected from O, S, Se, and Te,
at least one of X 3 and X 4 is selected from O, S, Se, and Te,
each of X 5 and X 6 are independently one of O, S, Se, Te, and CR b R c wherein each of R b to R c are independently one of hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, —OR 11 , wherein R 11 is a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 4 to C 30 cycloalkyl group, —OR 12 , wherein R 12 is a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, —C(═O)R 13 , wherein R 13 is a substituted or unsubstituted C 1 to C 30 alkyl group, —S(═O) 2 R 14 , wherein R 14 is a substituted or unsubstituted C 1 to C 30 alkyl group, and —NHC(═O)OR 15 , wherein R 15 is a substituted or unsubstituted C 1 to C 30 alkyl group,
each of R 1 to R 6 are independently one of hydrogen, —F, —Cl, —Br, —I, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkenyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
R 100 is hydrogen, —F, —Cl, —Br, —I, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkenyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, or a substituted or unsubstituted C 2 to C 30 heteroaryl group, and
x is an integer of 1 or 2.

3. The fused polycyclic heteroaromatic compound of claim 2 , wherein, in Chemical Formula 1A, each of R 1 to R 6 are independently one of a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkenyl group, a substituted or unsubstituted linear or branched C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloa

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Jeong Il
• Lee Bang Lin
• Chung Jong Won
• Jung Ji Young

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/0545

  Electricity · mapped topic

• H01L51/005 Primary

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic