Composition for photoelectric device, and photoelectric device, image sensor and electronic device including the same

Patent metadata

Field	Value
Publication number	US-12448397-B2
Application number	US-202217688051-A
Country	US
Kind code	B2
Filing date	Mar 7, 2022
Priority date	Mar 5, 2021
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

A composition for a photoelectric device includes a compound represented by Chemical Formula 1, and an image sensor and an electronic device including the same:

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

First claim

What is claimed is:

1. A composition for a photoelectric device, the composition comprising:
a p-type semiconductor compound represented by Chemical Formula 1 and an n-type semiconductor compound:

wherein, in Chemical Formula 1,
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 each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, each pair of R bb and R cc , R dd and R ee , R ff and R gg , or R mm and R nn are linked to each other to form a ring structure, and n1 of —(CR f R g ) n1 — is 1 or 2, or L is linked to Y 1 or Y 4 to provide a ring structure,
Y 1 to Y 6 are each independently N or CR k , wherein R k is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, 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, a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof,
X 1 is —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 each independently hydrogen, deuterium, a halogen, a cyano group, 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, a substituted or unsubstituted C6 to C20 aryloxy group, or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of R bb and R cc , R dd and R ee , or R ff and R gg are linked to each other to provide a ring structure,
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 each independently hydrogen, deuterium, a halogen, a cyano group, 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, a substituted or unsubstituted C6 to C20 aryloxy group or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of R bb and R cc , R dd and R ee , R ff and R gg , or R mm and R nn is linked to 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, 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 each 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 (—CN), 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, —SiR a R b R c , wherein R a , R b , and R c are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, or any combination thereof.

2. The composition of claim 1 , wherein the p-type semiconductor compound of Chemical Formula 1 is represented by Chemical Formula 2A:

wherein, in Chemical Formula 2A,
X 1 , X 2 , Ar 3 , R 1 , R 2 , Y 1 to Y 3 , Y 5 , and Y 6 are the same as X 1 , X 2 , Ar 3 , R 1 , R 2 , Y 1 to Y 3 , Y 5 , and Y 6 , respectively, in Chemical Formula 1,
L 1 is N, B, Si, Ge, or C, 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, a substituted or unsubstituted C5 to C30 heterocycloalkene group, or a condensed ring thereof.

3. The composition of claim 1 , wherein the p-type semiconductor compound of Chemical Formula 1 is represented by Chemical Formula 2B:

wherein, in Chemical Formula 2B,
X 1 , X 2 , Ar 3 , R 1 , R 2 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are the same as X 1 , X 2 , Ar 3 , R 1 , R 2 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 , respectively, in Chemical Formula 1, 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, a substituted or unsubstituted C5 to C30 heterocycloalkene group, or a condensed ring thereof.

4. The composition of claim 1 , wherein
X 1 is —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 each independently a halogen, a cyano group, a C1 to C20 alkyl group substituted with a halogen or a cyano group, a C1 to C20 alkoxy group substituted with a halogen or a cyano group, a C6 to C20 aryl group substituted with a halogen or a cyano group, a C6 to C20 aryloxy group substituted with a halogen or a cyano group, or a C3 to C20 heteroaryl group substituted with a halogen or a cyano group.

5. The composition of claim 1 , wherein the ring structures in X 1 , X 2 , and L of Chemical Formula 1 are each a spiro structure or a fused ring structure.

6. The composition of claim 1 , wherein the ring structures in X 1 , X 2 , and L of Chemical Formula 1 are each a fused ring structure or a moiety represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
X a and X b are each 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 each independently hydrogen, deuterium, a halogen, a cyano group, 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, a substituted or unsubstituted C6 to C20 aryloxy group, or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of R bb and R cc or R dd and R ee is linked to each other to provide a ring structure,
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 each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Jeong Il
• Ham Cheol
• Kim Hyeongju
• Fang Feifei
• Yun Sung Young
• Lim Youn Hee
• Hong Hye Rim

Classifications

• H10K30/80

  Constructional details · CPC title

• H10K30/84

  Layers having high charge carrier mobility · CPC title

• H10K30/20 Primary

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H10K30/40

  comprising a p-i-n structure, e.g. having a perovskite absorber between p-type and n-type charge transport layers · CPC title

• H10K85/6572

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