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

Patent metadata

Field	Value
Publication number	US-11401289-B2
Application number	US-202016910838-A
Country	US
Kind code	B2
Filing date	Jun 24, 2020
Priority date	Jun 25, 2019
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

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, the definition of each substituent is as described in the detailed description.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar is a substituted or unsubstituted C2 to C30 hydrocarbon cyclic group, a substituted or unsubstituted C6 to C30 heterocyclic group, or a fused ring thereof,
Ar has at least one functional group selected from C═O, C═S, C═Se, and C═Te,
X is O, S, Se, Te, S(═O), S(═O) 2 , SiR a R b , GeR c R d , or CR e R f (wherein R a , R b , R c , R d , R e , and R f are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and wherein R a , R b , R c , R d , R e , and R f are independently present and R a and R b , R c and R d , or R e and R f are linked to each other to provide a spiro structure),
Y 1 and Y 2 are independently O, S, Se, or Te, and
R 1 to R 4 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, a pentafluorosulfanyl group (—SF 5 ), a hydroxyl 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 independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof, or
adjacent two groups of R 1 to R 4 are linked to each other to provide a substituted or unsubstituted C5 to C30 hydrocarbon cyclic group or a substituted or unsubstituted C2 to C30 heterocyclic group.

2. The compound of claim 1 , wherein in Chemical Formula 1, Y 1 and Y 2 are the same or different.

3. The compound of claim 1 , wherein in Chemical Formula 1, X is the same as or different from Y 1 and Y 2 .

4. The compound of claim 1 , wherein
in Chemical Formula 1,
X is one of S, Se, and Te, and
Y 1 and Y 2 are independently one of S, Se, and Te.

5. The compound of claim 1 , wherein
in Chemical Formula 1, X is one of SiR a R b , GeR c R d , and CR e R f ,
Y 1 and Y 2 are independently one of O, S, Se, and Te.

6. The compound of claim 1 , wherein Ar is represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
Ar′ 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, Ar is a cyclic group represented by one of Chemical Formulae 4A to 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, a halogen, a cyano group, a cyano-containing group, or a combination thereof, wherein R 12 and R 13 are independently different and are linked with each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Baik Chul
• Choi Taejin
• Shin Ji Soo
• Yun Sung Young
• Park Kyung Bae
• Lee Gae Hwang
• Choi Yeong Suk
• Heo Chul Joon

Classifications

• H10K30/86

  Layers having high hole mobility, e.g. hole-transporting layers or electron-blocking layers · CPC title

• H10K30/85

  Layers having high electron mobility, e.g. electron-transporting layers or hole-blocking layers · CPC title

• H10K30/30

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

• C07F11/00 Primary

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

• H10F39/12

  Image sensors · CPC title