Near-infrared absorbers, near-infrared absorbing/blocking films and photoelectric devices and organic sensors and electronic devices

Patent metadata

Field	Value
Publication number	US-11849595-B2
Application number	US-202016944873-A
Country	US
Kind code	B2
Filing date	Jul 31, 2020
Priority date	Aug 2, 2019
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

A near-infrared absorber includes a compound represented by Chemical Formula 1. A near-infrared absorbing/blocking film, a photoelectric device, an organic sensor, and an electronic device may include the near-infrared absorber.In Chemical Formula 1, Ar1, Ar2, X1, L1, L2, R1, R2, R3, and R4 are the same as defined in the detailed description.

First claim

What is claimed is:

1. A near-infrared absorber, comprising:
a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar 1 is a first moiety represented by Chemical Formula A-1, the first moiety including a first aromatic ring and left and right linking groups:

wherein, in Chemical Formula A-1,
separate adjacent pairs of *'s inside the first aromatic ring are linking portions with separate, respective ones of an N—X 1 —N-containing pentagonal ring of Chemical Formula 1 and an N-containing hexagonal ring of Chemical Formula 1, and
*'s of the left and right linking groups are portions linked to separate, respective ones of L 1 and L 2 of Chemical Formula 1,

Ar 2 is a second moiety represented by Chemical Formula B-3b, the second moiety including a second aromatic ring:

wherein, in Chemical Formula B-3b,
Ar 3 and Ar 4 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group, and
*'s inside the second aromatic ring are linking portions with the N-containing hexagonal ring of Chemical Formula 1,

X 1 is O, S, Se, Te, S(═O), S(═O 2 ), NR a , CR b R c , or SiR d R e , wherein R a , R b , R c , and R d are independently hydrogen, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
L 1 and L 2 are same or different and are each represented by Chemical Formula C-1:

wherein, in Chemical Formula C-1,
Y 1 is O, S, Se, Te, S(═O), S(═O) 2 , NR a , or SiR b R c , wherein R a , R b , and R c are independently hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
R b and R c are independently present or linked to each other to form a ring, and
each * is a linking point with Chemical Formula 1,

R 1 , R 2 , R 3 , and R 4 are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted silyl group, a halogen, or a combination thereof, and
R 1 and R 2 are independently present or linked to each other to form a ring, and R 3 and R 4 are independently present or linked to each other to form a separate ring.

2. The near-infrared absorber of claim 1 , wherein
the second moiety represented by Chemical Formula B-3b is represented by Chemical Formula B-3bb, each moiety including at least one aromatic ring:

wherein, in Chemical Formula B-3bb,
hydrogen of each aromatic ring is present or is replaced by a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, a C6 to C20 aryl group, or a C3 to C20 heteroaryl group,
*'s inside the at least one aromatic ring are linking portions with an N-containing hexagonal ring of Chemical Formula 1, and
X a and X b are independently —O—, —S—, —Se—, —Te—, —NR a —, —SiR b R c —, or —GeR d R e —, wherein R a , R b , R c , R d , and R e are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group.

3. The near-infrared absorber of claim 1 , wherein in Chemical Formula 1, *—N(R 1 )(R 2 ) and *—N(R 3 )(R 4 ) are independently represented by Chemical Formula D-1 or Chemical Formula D-2:

wherein, in Chemical Formula D-1,
Ar 5 and Ar 6 are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, and
* is a linking point with Chemical Formula 1,

wherein, in Chemical Formula D-2,
Ar 7 and Ar 8 are independently a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NR a —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n —, or —(C(R h )═C(R i ))—, wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R b and R c , R d and R e , R f and R g , or R h and R i are independently present or are linked to each other to form a ring, and n of —(CR f R g ) n — is an integer of 1 or 2, and
* is a linking point with Chemical Formula 1.

4. The near-infrared absorber of claim 3 , wherein Chemical Formula D-1 is represented by Chemical Formula D-1a or D-1b:

wherein, in Chemical Formula D-1a,
Z 1 to Z 10 are independently N or CR a , wherein R a is hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z 1 to Z 10 are CR x , R x 's are independently present or two adjacent groups of Z 1 to Z 10 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula 1,

wherein, in Chemical Formula D-1b,
X a and X b are independently —O—, —S—, —Se—, —Te—, —NR a —, —SiR b R c —, or —GeR d R e —, wherein R a , R b , R c , R d , and R e are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z 1 to Z 6 are independently N or CR x , wherein R x is hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z 1 to Z 6 are CR x , R x 's are independently present or two adjacent groups of Z 1 to Z 6 are linked to each other to form a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula 1.

5. The near-infrared absorber of claim 3 , wherein Chemical Formula D-2 is represented by Chemical Formula D-2a, Chemical Formula D-2b, or Chemical Formula D-2c:

wherein, in Chemical Formula D-2a,
G is a single bond, —O—, —S—, —Se—, —Te—, —N═, —NR a —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n —, or —(C(R h )═C(R i ))—, wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R b and R c , R d

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Hwang Suk
• Kwon Ohkyu
• Park Bum Woo
• Lee Kwang Hee
• Leem Dong-Seok
• Choi Hyesung
• Lee Dongseon

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

• H10K30/30

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

• H10K30/20 Primary

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H10F39/12

  Image sensors · CPC title

• H10K85/655 Primary

  comprising only sulfur as heteroatom · CPC title