Compound, organic photoelectronic device and image sensor

Patent metadata

Field	Value
Publication number	US-9911920-B2
Application number	US-201514597050-A
Country	US
Kind code	B2
Filing date	Jan 14, 2015
Priority date	Jul 21, 2014
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

A compound is represented by Chemical Formula 1:

X 1 -T-X 2
wherein T is a substituted or unsubstituted fused thiophene moiety, and each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group.

First claim

What is claimed is:

1. A compound represented by the following Chemical Formula 1:
X 1 -T-X 2   [Chemical Formula 1]

wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:

wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, a heterocyclic group including at least one of a nitrogen atom (N) and a sulfur atom (S), or a combination thereof, and
B is a substituted or unsubstituted C 6 to C 30 aryl group.

2. The compound of claim 1 , wherein
the alkenylene group links the substituted or unsubstituted fused thiophene moiety with the electron withdrawing group.

3. The compound of claim 1 , wherein the electron withdrawing group is selected from the following Group 1:

wherein each of R 11 to R 26 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.

4. The compound of claim 1 , wherein the compound is represented by one of the following Chemical Formulae 1a to 1c:

wherein, in the above Chemical Formulae 1a to 1c,
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group, and
each of R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.

5. A compound for selectively absorbing light in a green wavelength region and represented by the following Chemical Formula 1:
X 1 -T-X 2   [Chemical Formula 1]

wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:

wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, or a heterocylic group including at least one of a nitrogen atom (N) and a sulfur atom (S), and
B is a substituted or unsubstituted C 6 to C 30 aryl group.

6. The compound of claim 5 , wherein the compound has a maximum absorption wavelength (λ max ) of about 470 nm to about 580 nm.

7. An organic photoelectronic device comprising:
an anode and a cathode facing each other; and
an active layer between the anode and the cathode, the active layer including a compound represented by the following Chemical Formula 1:
X 1 -T-X 2   [Chemical Formula 1]

wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:

wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, a heterocyclic group including at least one of a nitrogen atom (N) and a sulfur atom (S), or a combination thereof, and
B is a substituted or unsubstituted C 6 to C 30 aryl group.

8. The organic photoelectronic device of claim 7 , wherein
the alkenylene group links the substituted or unsubstituted fused thiophene moiety with the electron withdrawing group.

9. The organic photoelectronic device of claim 7 , wherein the electron withdrawing group is selected from the following Group 1:

wherein each of R 11 to R 26 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.

10. The organic photoelectronic device of claim 7 , wherein the compound is represented by one of the following Chemical Formulae 1a to 1c:

wherein, in the above Chemical Formulae 1a to 1c,
each of X 1 and X 2 are independently an orga

Assignees

• Samsung Electronics Co Ltd
• Samsung Electronics Co Ltd

Inventors

• Bulliard Xavier
• Yagi Tadao
• Sakurai Rie
• Lee Kwang Hee
• Leem Dong Seok
• Choi Hyesung
• Lim Seon Jeong
• Jin Yong Wan

Classifications

• H01L27/307

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic

• H01L51/424

  Electricity · mapped topic

• H01L51/0058 Primary

  Electricity · mapped topic

• H01L51/0069

  Electricity · mapped topic