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

Patent metadata

Field	Value
Publication number	US-12349592-B2
Application number	US-202117146850-A
Country	US
Kind code	B2
Filing date	Jan 12, 2021
Priority date	Jan 13, 2020
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

A compound of Chemical Formula 1, and an organic photoelectric device, an image sensor, and/or 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 and Ar 2 are independently a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof,
X 1 is —Se—, —Te—, or —NR a1 —, wherein R a1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
X 2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —SiR bb R cc —, —GeR d R e —, —GeR dd R ee —, —(CR f R g ) n1 —, —(CR ff R gg )—, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or —(C(R p )═N))—, wherein R a1 , R a2 , R b , R c , R d , R e , R f , R g , R m , R n , and R p are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and R bb and R cc , R dd and R ee , R ff and R gg , and R mm and R nn are linked with each other to provide a ring structure, and n1 of —(CR f R g ) n1 — is 1 or 2,
L is —O—, —S—, —Se—, —Te—, —NR a1 —, —BR a2 —, —SiR b R c —, —SiR bb R cc —, —GeR d R e —, —GeR dd R ee —, —(CR f R g ) n1 —, —(CR ff R gg )—, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, —(C(R p )═N))—, or a single bond, wherein R a1 , R a2 , R b , R c , R d , R e , R f , R g , R m , R n , and R p are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and R bb and R cc , R dd and R ee , R ff and R gg , and R mm and R nn are linked with each other to provide a ring structure, and n1 of —(CR f R g ) n1 — is 1 or 2,
when L is —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n1 —, —(C(R m )═C(R n ))—, or —(C(R p )═N))—, L is optionally linked with Ar 1 or Ar 2 to provide a ring structure,
Ar 3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof, and
R 1 and R 2 are independently 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 substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF 5 ), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiR a R b R c , wherein R a , R b , and R c are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group.

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

wherein, in Chemical Formula 2A,
X 1 , X 2 , L, Ar 3 , R 1 , and R 2 are the same as in Chemical Formula 1, and
Y 1 to Y 7 are independently N or CR k , wherein R k is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent R k 's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof.

3. The compound of claim 2 , wherein
in Chemical Formula 2A, Y 4 is N or CR k , wherein R k is a halogen, a cyano group, a C1 to C10 haloalkyl group, or a C1 to C10 cyanoalkyl group, or
Y 7 is N or CR k , wherein R k is a halogen, a cyano group, a C1 to C10 haloalkyl group, or a C1 to C10 cyanoalkyl group, and
X 2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n1 —, —(C(R m )═C(R n ))—, or —(C(R p )═N))—, wherein R a1 , R a2 , R b , R c , R d , R e , R f , R g , R m , R n , and R p are independently a halogen, a C1 to C20 haloalkyl group, or a C1 to C20 cyanoalkyl group.

4. The compound of claim 1 , wherein the compound is represented by Chemical Formula 2A-1 or Chemical Formula 2A-2:

wherein, in Chemical Formula 2A-1,
X 1 , X 2 , Ar 3 , R 1 , and R 2 are the same as in Chemical Formula 1,
L 1 is N, B, Si, Ge, or C,
Y 1 to Y 4 , Y 6 , and Y 7 are independently N or CR k , wherein R k is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent R k 's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
Cy is a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, a substituted or unsubstituted C5 to C30 cycloalkene group, or a substituted or unsubstituted C5 to C30 heterocycloalkene group, or a condensed ring thereof,

wherein, in Chemical Formula 2A-2,
X 1 , X 2 , Ar 3 , R 1 , and R 2 are the same as in Chemical Formula 1,
L 1 is N, B, Si, Ge, or C,
Y 2 to Y 7 are independently N or CR k , wherein R k is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent R k 's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
Cy is a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, a substituted or unsubstituted C5 to C30 cycloalkene group, or a substituted or unsubstituted C5 to C30 heterocycloalkene group, or a condensed ring thereof.

5. A compound represented by Chemical Formula 2B:

wherein, in Chemical Formula 2B,
X 1 is —Se—, —Te—, or —NR a1 —, wherein R a1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
X 2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —SiR bb R cc —, —GeR d R e —, —GeR dd R ee —, —(CR f R e ) n1 —, —(CR ff R gg )—, —(C(R m )

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lim Seon-Jeong
• Ishii Norihito
• Shibata Katsunori
• Jin Yong Wan
• Choi Taejin
• Park Kyung Bae
• Park Sung Jun
• Shin Jisoo
• Yun Sung Young

Classifications

• H10F39/1825

  Multicolour image sensors having stacked structure, e.g. NPN, NPNPN or multiple quantum well [MQW] structures · CPC title

• H10K39/32

  Organic image sensors · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K19/20

  comprising components having an active region that includes an inorganic semiconductor · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title