IP Library Granted Patent US 12,349,592
Granted Patent B2
US 12,349,592 · App. 17/146,850 · Granted Jul 1, 2025

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

Inventors: Seon-Jeong Lim (Yongin-si, KR); Norihito Ishii (Yokohama, JP); Katsunori Shibata (Hwaseong-si, KR); Yong Wan Jin (Seoul, KR); Taejin Choi (Suwon-si, KR); Kyung Bae Park (Hwaseong-si, KR); Sung Jun Park (Yongin-si, KR); Jisoo Shin (Suwon-si, KR); Sung Young Yun (Suwon-si, KR)
Assignee: Samsung Electronics Co., Ltd.
H10K85/657C07D471/16C07D517/16H10K85/654H10K85/6572H01L27/14647H10K19/20H10K30/30H10K39/32
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Quick Facts
Patent No.
US 12,349,592
App. No.
17/146,850
Granted
Jul 1, 2025
Kind
B2
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.

Claims (151)

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 )═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,

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,

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,

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,

Y 1 to Y 5 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

X 3 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 —, or —CR ff R gg —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R g 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 , and R ff and R gg are linked to each other to provide a ring structure.

6. The compound of claim 5 , wherein

in Chemical Formula 2B, 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 5 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.

7. A compound represented by Chemical Formula 2C:

wherein, in Chemical Formula 2C,

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,

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,

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,

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 e ) 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,

Y 1 to Y 5 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

X 3 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 —, or —CR ff R gg —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R g 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 , and R ff and R gg are linked to each other to provide a ring structure.

8. The compound of claim 7 , wherein

in Chemical Formula 2C, 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

X 3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, or —CR f R g —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R e are independently a halogen, a C1 to C20 haloalkyl group, or a C1 to C20 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.

9. A compound represented by Chemical Formula 2D:

wherein, in Chemical Formula 2D,

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 )═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,

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,

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,

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,

Y 1 to Y 5 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

X 3 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 —, or —CR ff R gg —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R g 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 , and R ff and R gg are linked to each other to provide a ring structure.

10. The compound of claim 9 , wherein

in Chemical Formula 2D, 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 3 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.

11. A compound represented by Chemical Formula 2E:

wherein, in Chemical Formula 2E,

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,

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,

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,

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,

Y 1 to Y 5 are 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

X 3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, —GeR dd R ee —, —CR f R g —, or —CR ff R gg —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R g 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 , and R ff and R gg are linked to each other to provide a ring structure.

12. The compound of claim 11 , wherein

in Chemical Formula 2E,

X 3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, or —CR f R g —, wherein R a1 , R a2 , R b , R c , R d , R e , R f , and R g are independently a halogen, a C1 to C20 haloalkyl group, or a C1 to C20 cyanoalkyl group, or

Y 3 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.

13. The compound of claim 1 , wherein in X 2 and L of Chemical Formula 1, the ring structure is a spiro structure or a fused ring structure.

14. The compound of claim 13 , wherein the spiro structure includes a moiety represented by one of moieties (1) to (9):

X a and X b are independently —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 —, or —GeR dd R ee —, wherein R a1 , R a2 , R b , R c , R d and R e 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 , and R dd and R ee , are linked to each other to provide a ring structure, and

L a is —O—, —S—, —Se—, —Te—, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n1 —, —(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 , 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.

15. The compound of claim 13 , wherein a hydrogen of on each ring is replaced by at least one substituent selected from 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, and a substituted or unsubstituted C6 to C20 aryloxy group.

16. The compound of claim 14 , wherein one or more CH groups present in the aromatic ring of the moieties (3), (4), (5), (6), and (7) is are replaced by N.

17. The compound of claim 1 , wherein Ar 3 is a cyclic group represented by Chemical Formula 4:

wherein, in Chemical Formula 4,

Ar 3′ is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heteroaryl group,

Z 1 is O, S, Se, or Te, and

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group.

18. The compound of claim 1 , wherein in Chemical Formula 1, Ar 3 is a cyclic group represented by one of Chemical Formula 5A to Chemical Formula 5F:

wherein, in Chemical Formula 5A,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

Z 3 is N or CR c , wherein R c is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,

R 11 , R 12 , R 13 , R 14 , and R 15 are the same or different and are independently 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, or a cyano-containing group, or a combination thereof, wherein R 12 , R 13 , R 14 , and R 15 are independently present or are adjacently linked to each other to provide a fused aromatic ring,

n is 0 or 1, and

* is a linking point,

wherein, in Chemical Formula 5B,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

Z 3 is O, S, Se, Te, or C(R a )(CN), wherein R a is hydrogen, a cyano group (CN), or a C1 to C10 alkyl group,

R 11 and R 12 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 C4 to C30 heteroaryl group, a halogen, or a cyano group (CN), or a combination thereof, and

* is a linking point,

wherein, in Chemical Formula 5C,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

R 11 , R 12 , and R 13 are the same or different and 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 C4 to C30 heteroaryl group, a halogen, or a cyano group (CN), or a combination thereof, and

* is a linking point,

wherein, in Chemical Formula 5D,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

Z 3 is N or CR c , wherein R c is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,

G 1 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are the same or different and are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R 11 , R 12 , and R 13 are the same or different and 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 C4 to C30 heteroaryl group, a halogen, a cyano group, or a cyano-containing group, or a combination thereof, wherein R 12 and R 13 are independently present or are linked to each other to provide a fused aromatic ring,

n is 0 or 1, and

* is a linking point,

wherein, in Chemical Formula 5E,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

Z 3 is N or CR c , wherein R c is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,

G 2 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are the same or different and are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R 11 , R 12 , and R 13 are the same or different and 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 C4 to C30 heteroaryl group, a halogen, a cyano group, or a cyano-containing group, or a combination thereof, and

n is 0 or 1, and

* is a linking point,

wherein, in Chemical Formula 5F,

Z 1 is O, S, Se, or Te,

Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,

R 11 is 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), or a cyano-containing group, or a combination thereof, and

G 3 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are the same or different and are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

19. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength range of greater than or equal to about 500 nm and less than or equal to about 600 nm in a thin film state.

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

21. A 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,

wherein the active layer comprises the compound of claim 1 .

22. An image sensor comprising:

the photoelectric device of claim 21 .

23. The image sensor of claim 22 , further comprising:

a semiconductor substrate integrated with a plurality of first photo-sensing devices configured to sense light in a blue wavelength region and a plurality of second photo-sensing devices configured to sense light in a red wavelength region, wherein

the photoelectric device is on the semiconductor substrate and configured to selectively sense light in a green wavelength region.

24. The image sensor of claim 23 , further comprising:

a color filter layer, wherein

the color filter layer includes a blue filter configured to selectively transmit light in a blue wavelength region and a red filter configured to selectively transmit light in a red wavelength region.

25. The image sensor of claim 23 , wherein the plurality of first photo-sensing devices and the plurality of second photo-sensing devices are stacked in a vertical direction in on the semiconductor substrate.

26. The image sensor of claim 22 , further comprising:

an organic photoelectric device including the photoelectric device;

a blue photoelectric device configured to selectively absorb light in a blue wavelength region;

a red photoelectric device configured to selectively absorb light in a red wavelength region, wherein

the organic photoelectric device is a green photoelectric device, and

the organic photoelectric device, the blue photoelectric device, and the red photoelectric device are stacked.

27. An electronic device comprising:

the image sensor of claim 22 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2021
From: LIM, SEON-JEONG; ISHII, NORIHITO; SHIBATA, KATSUNORI; JIN, YONG WAN; CHOI, TAEJIN; PARK, KYUNG BAE; PARK, SUNG JUN; SHIN, JISOO; YUN, SUNG YOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 054933/0222 →
Priority Claims (1)
KR 10-2020-0004232 · Jan 13, 2020 · national
Continuity (1)
Related Publication 20210234103A1 · Jul 29, 2021
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