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

Patent metadata

Field	Value
Publication number	US-10326083-B2
Application number	US-201715591259-A
Country	US
Kind code	B2
Filing date	May 10, 2017
Priority date	May 10, 2016
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

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

First claim

What is claimed is:

1. A compound comprising:
a structure 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, or a combination thereof in a condensed ring,
X is one of Se, Te, O, S(═O), S(═O) 2 , NR a , and SiR b R c (wherein each of R a , R b , and R c are independently one of hydrogen or a substituted or unsubstituted C1 to C10 alkyl group),
each of R 1 to R 3 are independently one of hydrogen, 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 halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof,
each of Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, and
G is one of a direct bond, —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —GeR i R j —, or —(C(R m )═C(R n ))— (wherein each of R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and R m and R n are linked to each other to provide a fused ring or R m and R n are not linked together to provide a fused ring, and n is an integer of 1, or 2).

2. The compound of claim 1 , wherein in Chemical Formula 1, at least one of Ar 1 and Ar 2 include a heteroatom at 1 position, and the heteroatom is one of nitrogen (N), sulfur (S), or selenium (Se).

3. The compound of claim 1 , wherein the structure is represented by at least one of Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 2-3, Chemical Formula 2-4, or Chemical Formula 2-5:

wherein, in Chemical Formula 2-1 to Chemical Formula 2-5,
R 4a to R 4d and R 5a to R 5d 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, or a combination thereof,
two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 4a to R 4d are not linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and
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 or two adjacent groups of R 5a to R 5d are not linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

4. The compound of claim 3 , wherein the structure is represented by Chemical Formula 2-2.

5. The compound of claim 3 , wherein the structure is represented by Chemical Formula 2-3.

6. The compound of claim 3 , wherein the structure is represented by at least one of Chemical Formula 2-4 or Chemical Formula 2-5.

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

wherein, in Chemical Formula 3,
Ar′ is one of a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, or a combination thereof in a condensed ring, and
Z 1 is one of O or 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, or a cyano-containing group, provided that at least one of R b and R c is a cyano group or a cyano-containing group.

8. The compound of claim 1 , wherein in Chemical Formula 1, a ring group represented by Ar and bound to a methine group is represented by one of Chemical Formula 4-1, Chemical Formula 4-2, Chemical Formula 4-3, or Chemical Formula 4-4:

wherein, in Chemical Formula 4-1,
Z 1 is O or 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, or 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 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, or a combination thereof, or R 12 and R 13 are independently linked with each other to provide an aromatic ring or R 14 and R 15 are independently linked with each other to provide an aromatic ring,
m1 is 0 or 1,
n1 is O or 1, and
indicates a linking position with a methine group,

wherein, in Chemical Formula 4-2,
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), or a C1 to C10 alkyl group),
R 16 and R 17 are independently one of hydrogen, 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
indicates a linking position with a methine group,

wherein, in Chemical Formula 4-3,
R 18 to R 20 are independently one of hydrogen, 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), a cyano-containing group, or a combination thereof, and
indicates a linking position with a methine group,

wherein, in Chemical Formula 4-4,
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), or a C1 to C10 alkyl group),
Y 3 is one of O, S, Se, and Te,
Y 4 is one of N or NR f ,
Y 5 is one of CR g , C═O, C═S, C═(CR h )(CN), and a group represented by Chemical Formula 4-4′,
when Y 2 is not O, Y 5 is C═O and when Y 5 is not C═O, Y 2 is O,
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 C1 to C30 alkoxy group, a substituted or unsub

Assignees

• Samsung Electronics Co Ltd

Inventors

• Yagi Tadao
• Bulliard Xavier
• Choi Hyesung
• Sakurai Rie
• Shibuya Hiromasa
• Lim Youn Hee
• Yun Sung Young
• Lee Gae Hwang
• Lee Kwang Hee
• Leem Dong-Seok

Classifications

• C07D421/14

  containing three or more hetero rings · CPC title

• H01L51/0053

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0062

  Electricity · mapped topic