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

Patent metadata

Field	Value
Publication number	US-10276802-B2
Application number	US-201715461914-A
Country	US
Kind code	B2
Filing date	Mar 17, 2017
Priority date	Apr 6, 2016
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

Example embodiments provide a compound of Chemical Formula 1, and an organic photoelectric device, an image sensor, and an electronic device including the same.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar is selected from a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, and a condensed ring of two or more of the foregoing rings,
X 1 is Se,
each of R 1 to R 3 are independently selected from hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof, and
each of Ar 1 and Ar 2 are independently selected from a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 3 to C 30 heteroaryl group, provided that at least one of Ar 1 and Ar 2 is a heteroaryl group including at least one nitrogen (N) at an ortho position with respect to a bond with the nitrogen (N) of Chemical Formula 1.

2. The compound of claim 1 , wherein, in Chemical Formula 1, at least one of Ar 1 and Ar 2 is selected from a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted prazolyl group, a substituted or unsubstituted midazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl 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 indolyl 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, a substituted or unsubstituted pyridopyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted selenophenyl group, and a substituted or unsubstituted benzoselenophenyl group, and the functional groups may include at least one nitrogen (N) at an ortho position with respect to a bond with the nitrogen (N).

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

wherein, in Chemical Formula 2,
Ar is selected from a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, and a condensed ring of two or more of the foregoing rings,
X 1 is Se,
each of R 1 to R 3 are independently selected from hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof,
each of R 4a to R 4e are independently selected from hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof, or optionally two adjacent groups of R 4a to R 4e are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring,
a is an integer of 0 or 1,
X 2 is nitrogen (N), and
Ar′ 1 is heteroaryl group including at least one nitrogen (N) at an ortho position with respect to a bond with the nitrogen (N).

4. The compound of claim 3 , wherein, in Chemical Formula 2, Ar′ 1 is selected from a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl 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 indolyl 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, a substituted or unsubstituted pyridopyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted selenophenyl group, and a substituted or unsubstituted benzoselenophenyl group.

5. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formulae 3-1 to 3-6:

wherein, in Chemical Formulae 3-1 to 3-6,
Ar is selected from a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, and a condensed ring of two or more of the foregoing rings,
X 1 is Se,
each of R 1 to R 3 are independently selected from hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof,
each of R 4a to R 4e or R 5a to R 5d are independently selected from hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, and a combination thereof, or optionally two adjacent groups of R 4a to R 4e are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring and optionally two adjacent groups of R 5a to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and
each of a and b are independently an integer of 0 or 1.

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

wherein, in Chemical Formula 4,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shibuya Hiromasa
• IMASE Tatsuya
• Sakurai Rie
• Bulliard Xavier
• Choi Hyesung
• Yagi Tadao
• Yun Sung Young
• Lee Gae Hwang
• Lee Kwang Hee
• Leem Dong-Seok
• Choi Yeong Suk

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D421/14

  containing three or more hetero rings · CPC title

• C07F11/005

  compounds without a metal-carbon linkage · CPC title

• C07D421/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• H05B33/14 Primary

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title