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

Patent metadata

Field	Value
Publication number	US-11145822-B2
Application number	US-201816165005-A
Country	US
Kind code	B2
Filing date	Oct 19, 2018
Priority date	Oct 20, 2017
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

A compound of 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 3 is a cyclic group represented by Chemical Formula 2A:

wherein, in Chemical Formula 2A,
Y 1 is one of N or CR a ,
wherein R a is one of hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,
R 11 , R 12 , R 13 , R 14 , and R 15 are one of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or R 12 and R 13 and R 14 and R 15 are independently link with each other to provide an aromatic ring,
m1 is 0 or 1,
n in Chemical Formula 2A is 0 or 1, and
* is a linking point,
R 1 to R 3 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 (—CN), a cyano-containing group, or a combination thereof,
R 1 and R 2 independently are present or linked with each other to provide a ring,
Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a combination thereof in a condensed ring, and
G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj , —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond, wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and
n in —(CR d R e ) n — is 1 or 2.

2. The compound of claim 1 , wherein in Chemical Formula 1,
at least one of Ar 1 and Ar 2 includes a heteroatom at No. 1 position, and
the heteroatom is one of nitrogen (N), sulfur (S), or selenium (Se).

3. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4A:

wherein, in Chemical Formula 4A,
G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond, wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in —(CR d R e ) n — is 1 or 2, and
R 4a to R 4d and R 5a to R 5d 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 (—CN), a cyano-containing group, or a combination thereof, or
two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5a to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

4. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4B:

wherein, in Chemical Formula 4B,
G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))— or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in —(CR d R e ) n — is 1 or 2, and
R 4a to R 4d and R 5b to R 5d 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 (—CN), a cyano-containing group, or a combination thereof, or
two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5b to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

5. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4C:

wherein, in Chemical Formula 4C,
G is one of —(CR d R e ) n , —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))— or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in —(CR d R e ) n — is 1 or 2, and
R 4b to R 4d and R 5b to R 5d 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 (—CN), a cyano-containing group, or a combination thereof, or
two adjacent groups of R 4b to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5b to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shin Jisoo
• Choi Yeong Suk
• Shibata Katsunori
• Choi Taejin
• Yun Sungyoung
• Kwon Ohkyu
• Kim Sangmo
• Shibuya Hiromasa
• Lee Gae Hwang
• Jin Yong Wan
• Choi Hyesung
• Baik Chul
• Hong Hyerim

Classifications

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D409/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07F11/00

  Compounds containing elements of Groups 6 or 16 of the Periodic Table · CPC title

• C07F7/30

  Germanium compounds · CPC title

• C07D421/04

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