Compound for organic photoelectric device and organic photoelectric device image sensor, and electronic device including the same

Patent metadata

Field	Value
Publication number	US-10290812-B2
Application number	US-201514951718-A
Country	US
Kind code	B2
Filing date	Nov 25, 2015
Priority date	Nov 25, 2014
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

A compound for an organic photoelectric device is represented by Chemical Formula 1, and an organic photoelectric device, an image sensor and an electronic device include the same.

First claim

What is claimed is:

1. A compound for an organic photoelectric device represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings,
X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein each of R a and R b are independently one of hydrogen and a substituted or unsubstituted C 1 to C 10 alkyl group,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group, and
each of R 1 to R 3 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 halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof
wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength region of greater than about 530 nm and less than or equal to about 575 nm.

2. The compound of claim 1 , wherein the compound has 4 to 7 aromatic rings.

3. The compound of claim 1 , wherein at least one of the Ar 1 and Ar 2 groups is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted phenanthrenyl group.

4. The compound of claim 1 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
Ar′ is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings, and
Z 1 is one of O and CR c R d , wherein each of R c and R d are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c and R d is one of a cyano group and a cyano-containing group.

5. The compound of claim 1 , wherein in Chemical Formula 1, a cyclic group represented by Ar and bound to a methine group is a cyclic group represented by one of Chemical Formulae 3-1 to 3-3:

wherein, in Chemical Formulae 3-1 to 3-3,
Z 1 is one of O and CR c R d , wherein each of R c and R d are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c and R d is one of a cyano group and a cyano-containing group,
Y 1 is one of N and CR e , wherein R e is one of hydrogen and a substituted or unsubstituted C 1 to C 10 alkyl group,
Y 3 is one of O, S, Se, and Te,
Y 4 is one of N and NR 18 ,
Y 5 is one of CR 19 and C═C(R 20 )(CN),
each of R 11 , R 12 and R 15 to R 20 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 4 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group and a combination thereof,
m1 is 0 or 1,
m2 is an integer ranging from 0 to 4, and
n is 0 or 1.

6. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 4-1 to 4-3:

wherein, in Chemical Formulae 4-1 to 4-3,
X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b wherein each of R a and R b are independently one of hydrogen and a substituted or unsubstituted C 1 to C 10 alkyl group,
Z 1 is one of O and CR c R d wherein R c and R d are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group, and a cyano-containing group, provided at least one of R c and R d is one of a cyano group and a cyano-containing group,
Y 1 is one of N and CR e wherein R e is one of hydrogen and a substituted or unsubstituted C 1 to C 10 alkyl group,
Y 3 is one of O, S, Se, and Te,
Y 4 is one of N and NR 18 ,
Y 5 is one of CR 19 and C═C(R 20 )(CN),
each of R 1 to R 3 , R 11 , R 12 and R 15 to R 20 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 4 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group and combination thereof,
m1 is 0 or 1,
m2 is an integer ranging from 0 to 4,
n is 0 or 1,
each of R 21 to R 23 are independently one of hydrogen, a halogen, a cyano group (—CN), a cyano-containing group, a substituted or unsubstituted C 1 to C 6 alkyl group, a substituted or unsubstituted C 1 to C 6 alkoxy group, and a combination thereof, and
p is an integer ranging from 0 to 3, q is an integer ranging from 0 to 4, and r is an integer ranging from 0 to 5.

7. The compound of claim 1 , wherein the compound shows a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 110 nm in a thin film state.

8. The compound of claim 1 , wherein the compound has a thermal decomposition of greater than or equal to about 280° C.

9. An organic photoelectric device comprising:
a first electrode and a second electrode facing each other; and
an active layer between the first electrode and the second electrode, the active layer including a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar is one of a substituted or unsubstituted 5-membered ring, a substituted or unsubstituted 6-membered ring, and a condensed ring of two or more of the foregoing rings,
X is one of Se, Te, S(═O), S(═O) 2 , and SiR a R b , wherein R a and R b are independently one of hydrogen and a substituted or unsubstituted C 1 to C 10 alkyl group,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group, and
each of R 1 to R 3 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 halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof,
wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength region of greater than about 530 nm and less than or equal to about 575 nm.

10. The organic photoelectric device of claim 9 , wherein the compound has 4 to 7 aromatic rings.

11. The organic photoelectric device of claim 9 , wherein at least one of the Ar 1 and Ar 2 groups is one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted phenanthrenyl group.

12. The organi

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lim Seon-Jeong
• Ro Takkyun
• Yagi Tadao
• Park Kyung Bae
• Yun Sung Young
• Jin Yong Wan
• Heo Chul-Joon

Classifications

• H01L51/0062

  Electricity · mapped topic

• H01L27/307

  Electricity · mapped topic

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C09B23/04

  one >CH- group, e.g. cyanines, isocyanines, pseudocyanines · CPC title

• H01L51/0061

  Electricity · mapped topic