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

Patent metadata

Field	Value
Publication number	US-11713326-B2
Application number	US-202016938031-A
Country	US
Kind code	B2
Filing date	Jul 24, 2020
Priority date	Jul 26, 2019
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

Abstract

A compound of Chemical Formula 1, and an organic 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 is a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
Ar 2 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group, a substituted or unsubstituted C6 to C30 heterocyclic group, or a fused ring thereof,
Ar 2 has at least one functional group selected from C═O, C═S, C═Se, and C═Te
X is Se, Te, SiR a R b , or GeR c R d (wherein R a , R b , R c , and R d are independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, and wherein R a , R b , R c , and R d are independently present or R a and R b or R c and R d are linked with each other to provide a spiro structure), and
R 1 to R 3 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 (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and Re are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof.

2. The compound of claim 1 , wherein in Chemical Formula 1, R 1 is a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group.

3. The compound of claim 1 , wherein in Chemical Formula 1, Ar 1 is a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted indene, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted fluorine, or a substituted or unsubstituted acenaphthylene.

4. The compound of claim 1 , A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1, Ar 1 is a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted indole, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted carbazole, a substituted or unsubstituted phenazine, or a substituted or unsubstituted phenanthroline.

5. The compound of claim 1 , wherein in Chemical Formula 1, X is one of Se and Te.

6. The compound of claim 1 , wherein Are is a cyclic group represented by Chemical Formula 3:
[Chemical Formula 3]

wherein, in Chemical Formula 3,
Ar 1 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.

7. The compound of claim 1 , wherein in Chemical Formula 1, Are is a cyclic group represented by one of Chemical Formula 4A to Chemical Formula 4F:

wherein, in Chemical Formula 4A,
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 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 (—CN), a cyano-containing group, or a combination thereof, wherein R 11 , R 12 , R 13 , R 14 , and R 15 are independently present or at least one of R 12 and R 13 and R 14 and R 15 is linked with each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,

wherein, in Chemical Formula 4B,
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,
Y 1 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, a cyano group (—CN), or a combination thereof, and
* is a linking position,

wherein, in Chemical Formula 4C,
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 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, a cyano-containing group, or a combination thereof, and
* is a linking position,

wherein, in Chemical Formula 4D,
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 independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
R 11 , R 12 , and R 13 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

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shin Jisoo
• Baik Chul
• Yun Sung Young
• Choi Taejin
• Park Kyung Bae
• Lee Gae Hwang
• Choi Yeong Suk
• Heo Chul Joon
• Hong Hye Rim

Classifications

• 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

• H10F39/12

  Image sensors · CPC title

• C07D517/04 Primary

  Ortho-condensed systems · CPC title

• H10K85/621

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title