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

Patent metadata

Field	Value
Publication number	US-9960362-B2
Application number	US-201715609125-A
Country	US
Kind code	B2
Filing date	May 31, 2017
Priority date	May 31, 2016
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

A compound is represented by Chemical Formula 1, and an organic photoelectric device, an image sensor, and an electronic device include the compound.

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 is one of a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, and a combination thereof in a condensed ring,
X is one of O and NR a (wherein R a is one of hydrogen and a substituted or unsubstituted C1 to C10 alkyl group),
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, and
each of R 1 , R 2 , and R 3 are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof.

2. The compound of claim 1 , wherein at least one of Ar 1 and Ar 2 is independently one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzotriazinyl group, a substituted or unsubstituted pyridopyrazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, and a substituted or unsubstituted pyridopyridazinyl group.

3. The compound of claim 1 , wherein, in Chemical Formula 1, a ring group represented by Ar bound to a methine group is represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
Ar′ is one of a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, and a combination thereof in a condensed ring, and
Z 1 is one of O and CR b R c , wherein R b and R c are independently one of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, and a cyano-containing group, provided that at least one of R b and R c is a cyano group or a cyano-containing group.

4. The compound of claim 1 , wherein, in Chemical Formula 1, a ring group represented by Ar bound to a methine group is represented by Chemical Formula 3-1:

wherein, in Chemical Formula 3-1,
Z 1 is one of O and CR b R c (wherein R b and R c are independently one of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, and a cyano-containing group, provided that at least one of R b and R c is a cyano group or a cyano-containing group),
Y 1 is one of N and CR d (wherein R d is one of hydrogen and a substituted or unsubstituted C1 to C10 alkyl group),
each of R 1 , R 12 , R 13 , R 14 , and R 15 are independently one of hydrogen, 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, and a combination thereof, or R 12 and R 13 and R 14 and R 15 are independently linked with each other to form an aromatic ring,
m1 is 0 or 1, and
n is 0 or 1.

5. The compound of claim 1 , wherein, in Chemical Formula 1, a ring group represented by Ar bound to a methine group is represented by Chemical Formula 3-2:

wherein, in Chemical Formula 3-2,
Y 2 is one of O, S, Se, Te, and C(R e )(CN) (wherein R e is one of hydrogen, a cyano group (—CN), and a C1 to C10 alkyl group), and
each of R 16 and R 17 are independently one of hydrogen, 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), and a combination thereof.

6. The compound of claim 1 , wherein, in Chemical Formula 1, a ring group represented by Ar bound to a methine group is represented by Chemical Formula 3-3:

wherein, in Chemical Formula 3-3,
each of R 18 to R 20 are independently one of hydrogen, 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, and a combination thereof.

7. The compound of claim 1 , wherein, in Chemical Formula 1, a ring group represented by Ar bound to a methine group is a ring group represented by Chemical Formula 3-4:

wherein, in Chemical Formula 3-4,
Y 3 is one of O, S, Se, and Te,
Y 4 is one of N and NR f ,
Y 5 is one of CR 9 and C═(CR h )(CN), and
each of R f , R g , and R h are independently one of hydrogen, 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, and a combination thereof.

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

wherein, in Chemical Formula 4-1,
Z 1 is one of O and CR b R c (wherein each of R b and R c are independently one of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, and a cyano-containing group, provided that at least one of R b and R c is a cyano group or a cyano-containing group),
Y 1 is one of N and CR d (wherein R d is one of hydrogen and a substituted or unsubstituted C1 to C10 alkyl group),
each of R 11 , R 12 , R 13 , R 14 , and R 15 are independently one of hydrogen, 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, and a combination thereof or R 12 and R 13 and R 14 and R 15 are independently linked with each other to form an aromatic ring,
m1 is 0 or 1,
n is 0 or 1,
each of R 21 and R 22 are independently one of hydrogen, a halogen, a cyano group (—CN), a cyano-containing group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C1 to C6 alkoxy group, and a combination thereof,
p is an integer ranging from 0 to 3, and
q is an integer ranging from 0 to 4.

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

Assignees

• Samsung Electronics Co Ltd

Inventors

• Bulliard Xavier
• Yagi Tadao
• Sakurai Rie
• Shibuya Hiromasa
• Lee Kwang Hee
• Leem Dong-Seok
• Choi Hyesung

Classifications

• H01L51/0046

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/0065

  Electricity · mapped topic

• H01L51/0053

  Electricity · mapped topic

• H01L51/0061 Primary

  Electricity · mapped topic