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

Patent metadata

Field	Value
Publication number	US-10461256-B2
Application number	US-201715611901-A
Country	US
Kind code	B2
Filing date	Jun 2, 2017
Priority date	Jun 3, 2016
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

A compound represented by Chemical Formula 1, and a photoelectric device, an image sensor, and an electronic device including the same are disclosed.

In Chemical Formula 1, each substituent is the same as defined in the detailed description.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar 1 to Ar 3 are independently one of a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heterocyclic group, and a combination thereof in a condensed ring,
R 3 is one of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, and a combination thereof,
G is one of a single bond, —O—, —S—, —Se—, —N═, —(CR f R g ) k —, —NR h —, —SiR i R j —, —GeR k R l , —(C(R m )═C(R n ))—, and SnR o R p wherein R f , R g , R h , R i , R j , R k , R l , R m , R n , R o and R p are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C6 to C12 aryl group, and R i and R j , R k and R l , R m and R n , and R o and R p are independently present or linked with each other to provide a ring, and k is one of 1 and 2,
Z 1 is one of O or CR b R c , wherein R b and R c are independently one of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, and a cyano-containing group, provided that at least one of R b and R c is a cyano group or a cyano-containing group, and
L 1 is one of linking groups of Group 1,

wherein, in Group 1,
X 1 is one of —Se—, —Te—, —O—, —S(═O)—, —S(═O) 2 —, —NR a —, —SiR b R c —, and —GeR d R e —,
X 2 and X 3 are independently one of —S—, —Se—, —Te—, —O—, —S(═O)—, —S(═O) 2 —, —NR a —, —SiR b R c —, and —GeR d R e —,
R a to R e are independently one of hydrogen and a substituted or unsubstituted C1l to C10 alkyl group,
R 1 , R 2 , R 4 , and R 5 are independently one of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, and a combination thereof, and
* is a linking point.

2. The compound of claim 1 , wherein R 3 is one of hydrogen, deuterium, and a methyl group.

3. The compound of claim 1 , wherein
at least one of Ar 1 and Ar 2 is a substituted or unsubstituted C3 to C30 heterocyclic group including at least one hetero atom selected from nitrogen (N), sulfur (S), selenium (Se), and a combination thereof.

4. The compound of claim 3 , wherein R 3 is one of hydrogen, deuterium, and a methyl group.

5. The compound of claim 1 , wherein Ar 3 is a condensed ring of a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 arene group, and a substituted or unsubstituted C3 to C30 heterocyclic group.

6. The compound of claim 5 , wherein Ar 3 is a condensed ring of a substituted or unsubstituted phenylene group and a substituted or unsubstituted heterocyclic group including one of S, Se, Ge, and Te.

7. The compound of claim 6 , wherein R 3 is one of hydrogen, deuterium, and a methyl group.

8. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 1-A to 1-D4:

wherein in Chemical Formulae 1-D1 to 1-D4,
G 11 and G 12 are independently one of —S—, —Se—, —Te—, —GeR x R y —, and —CR z R w —, wherein R x , R y , R z , and R w are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, and a substituted or unsubstituted C6 to C10 aryl group,
wherein, in Chemical Formulae 1-A to 1-D4,
R 6a to R 6d and R 7a to R 7d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, and a combination thereof,
R 6a to R 6d are independently present or two adjacent groups thereof are linked with each other to provide a fused cycle, and R 7a to R 7d are independently present or two adjacent groups thereof are linked with each other to provide a fused cycle.

9. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 1-E to 1-G:

wherein, in Chemical Formulae 1-E to 1-0,
Y 1 to Y 5 are independently one of N and CR d , wherein R d is one of hydrogen and a substituted or unsubstituted C1 to C10 alkyl group,
R 11 to R 13 are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, and a combination thereof,
n is 0 or 1, and
G 21 and G 22 are independently one of —S—, —Se—, —GeR x R y —, and —Te—, wherein R x and R y are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, and a substituted or unsubstituted C6 to C10 aryl group.

10. The compound of claim 9 , wherein at least one of Y 1 to Y 4 is N.

11. The compound of claim 9 , wherein at least one of Ar 1 and Ar 2 is a C3 to C30 heteroarylene group including at least one hetero atom selected from nitrogen (N), sulfur (S), selenium (Se), and a combination thereof.

12. The compound of claim 9 , wherein R 3 is one of hydrogen, deuterium, and a methyl group.

13. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 1-H to 1-S4:

wherein, in Chemical Formulae 1-H to 1-S4,
G 11 and G 12 are independently one of —S—, —Se—, —Te—, —GeR x R y —, and —CR z R w —, wherein R x , R y , R z , and R w are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, and a substituted or unsubstituted C6 to C10 aryl group,
R 6a to R 6d and R 7a to R 7d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Yeong Suk
• Kwon Ohkyu
• Lim Youn Hee
• Choi Hyesung
• Han Moon Gyu
• Shibuya Hiromasa
• Jin Yong Wan
• Shibata Katsunori

Classifications

• H04N23/54

  Mounting of pick-up tubes, electronic image sensors, deviation or focusing coils · CPC title

• C07D513/14

  Ortho-condensed systems · CPC title

• C07B59/002

  Heterocyclic compounds · CPC title

• C07D421/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D421/14 Primary

  containing three or more hetero rings · CPC title