Infrared absorbing polymer, infrared absorbing/blocking film, photoelectric device, organic sensor, and electronic device

Patent metadata

Field	Value
Publication number	US-11820859-B2
Application number	US-202117242724-A
Country	US
Kind code	B2
Filing date	Apr 28, 2021
Priority date	Apr 29, 2020
Publication date	Nov 21, 2023
Grant date	Nov 21, 2023

Abstract

An infrared absorbing polymer includes a first structural unit represented by Chemical Formula 1 and a second structural unit including at least one of Chemical Formula 2A to Chemical Formula 2. The infrared absorbing polymer may be included in an infrared absorbing/blocking film, a photoelectric device, a sensor, and an electronic device.

First claim

What is claimed is:

1. An infrared absorbing polymer, comprising:
a first structural unit represented by Chemical Formula 1 and a second structural unit including at least one of Chemical Formula 2A to Chemical Formula 2I:

wherein, in Chemical Formula 1,
Ar is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C3 to C30 heteroaromatic ring, or a combination thereof,
X is O, S, Se, Te, S(═O), S(═O 2 ), NR a , CR b R c , SiR d R e , GeR f R g , CR h ═CR i , or CR hh ═CR ii , wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, deuterium, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof, and R hh and R ii are linked to each other to form an aromatic ring, and
R 1 and R 2 are a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, or R 1 and R 2 are linked to each other to form a substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group,

wherein, in Chemical Formula 2A,
X 1 is Se, Te, S(═O), S(═O) 2 , NR a , SiR d R e , or GeR f R g , wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, deuterium, a C1 to C20 alkyl group, a C1 to C20 haloalkyl group, a C6 to C20 aryl group, a C3 to C20 heteroaryl group, a halogen, a cyano group, or a combination thereof,
in Chemical Formulas 2B to 2I,
X 1 to X 3 are independently S, Se, Te, S(═O), S(═O) 2 , NR a , SiR d R e , or GeR f R g , wherein R a , R b , R c , R d , R e , R f , R g , R h , and R i are independently hydrogen, deuterium, a C1 to C20 alkyl group, a C1 to C20 haloalkyl group, a C6 to C20 aryl group, a C3 to C20 heteroaryl group, a halogen, a cyano group, or a combination thereof, provided that at least one of X 1 and X 2 is not S in Chemical Formulas 2B, 2C, 2F, and 2G, and
X 2 is not SiR d R e or GeR f R g in Chemical Formula 2D,
Z 1 and Z 2 are independently N or CR x , wherein R x is hydrogen, deuterium, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH 3 group, a C1 to C10 alkylsilyl group, a —NH 2 group, 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,
Y 1 and Y 2 are independently O, S, Se, or Te,
in Chemical Formula 2H, n is 1,
in Chemical Formula 2I, n is 0 or 1, and
at least one hydrogen of each aromatic ring is optionally replaced by deuterium, a halogen, a cyano group, a C1 to C30 alkyl group, a C1 to C30 alkoxy group, a C1 to C30 haloalkyl group, a C6 to C30 aryl group, a C6 to C30 aryloxy group, a —SiH 3 group, or a C1 to C30 alkylsilyl group, wherein
the infrared absorbing polymer comprises about 20 mol % to about 50 mol % of the first structural unit and about 50 mol % to 80 mol % of the second structural unit.

2. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, Ar is benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted tetracene, a substituted or unsubstituted pyrene, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, or a substituted or unsubstituted phenanthroline.

3. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, Ar is one of the moieties represented by Chemical Formula A-1:

wherein, in Chemical Formula A-1,
at least one hydrogen of each aromatic ring is optionally replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH 3 group, or a C1 to C10 alkylsilyl group, and
* inside the aromatic ring is a portion that is bound to the N—X—N-containing ring and the pyrazine ring of Chemical Formula 1.

4. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, Ar is one of the moieties represented by Chemical Formula A-2:

wherein, in Chemical Formula A-2,
at least one hydrogen of each aromatic ring is optionally replaced by deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a —SiH 3 group, or a C1 to C10 alkylsilyl group, and
* inside the aromatic ring is a portion that is bound to the N—X—N-containing ring and the pyrazine ring of Chemical Formula 1.

5. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, the substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group formed by linking R 1 and R 2 to each other is a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted acenaphthene, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted tetracene or a substituted or unsubstituted pyrene; or a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted phenanthroline, a substituted or unsubstituted pyrimidine, or a substituted or unsubstituted benzodithiophene.

6. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, the substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group formed by linking R 1 and R 2 to each other is one of the moieties represented by Chemical Formula B-1 and Chemical Formula B-2:

wherein, in Chemical Formula B-1,
at least one hydrogen of each aromatic ring is optionally replaced by a halogen, a cyano group, a C1 to C30 alkyl group, a C1 to C30 alkoxy group, a C1 to C30 haloalkyl group, a —SiH 3 group, a C1 to C30 alkylsilyl group, a C6 to C30 aryl group, or a C3 to C30 heteroaryl group, and
* inside the aromatic ring is a portion that is bound to the pyrazine ring of Chemical Formula 1,

wherein, in Chemical Formula B-2,
at least one hydrogen of each aromatic ring is optionally replaced by a halogen, a cyano group, a C1 to C30 alkyl group, a C1 to C30 alkoxy group, a C1 to C30 haloalkyl group, a —SiH 3 group, a C1 to C30 alkylsilyl group, a C6 to C30 aryl group, a C6 to C30 aryloxy group, or a C3 to C30 heteroaryl group, and
* inside the aromatic ring is a portion that is bound to the pyrazine ring of Chemical Formula 1.

7. The infrared absorbing polymer of claim 1 , wherein in Chemical Formula 1, the substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group formed by linking R 1 and R 2 to each other is one of moieties represented by Chemical Formula B-3-1 or Chemical Formula B-3-2:

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jae Jun
• Kwon Ohkyu
• Kim Rae Sung
• Kim Hwang Suk
• Park In Sun
• Leem Dong-Seok

Classifications

• H10K30/30

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

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• C08G61/126 Primary

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• G02B5/208

  for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation · CPC title

• G02B5/223

  containing organic substances, e.g. dyes, inks or pigments · CPC title