N-type semiconductor, and organic photoelectric device, image sensor, and electronic device including the same

Patent metadata

Field	Value
Publication number	US-11737359-B2
Application number	US-202017092399-A
Country	US
Kind code	B2
Filing date	Nov 9, 2020
Priority date	Nov 7, 2019
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

Disclosed are an n-type semiconductor including compound represented by Chemical Formula 1 or Chemical Formula 2, an image sensor, and an electronic device.In Chemical Formula 1 and Chemical Formula 2, each substituent is as defined in the detailed description.

First claim

What is claimed is:

1. An n-type semiconductor comprising a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 , X 2 , and X 3 are CR a or N, wherein R a is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
L 1 , L 2 , and L 3 are independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, or a substituted or unsubstituted C2 to C30 alkynylene group that includes at least one linker selected from —NR b —, —C(═O)—, —S(═O)—, —OC(═O)—, —C(═O)O—, —S(═O) 2 —, —Si(R e R d ) 2 —, and —C(═O)NR e —, wherein, R b , R e , R d , and R e are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group, and
Ar 1 , Ar 2 , and Ar 3 are independently C2 to C30 N-containing heteroaryl group, a C6 to C30 aryl group having at least one electron withdrawing functional group (EWG), or a C2 to C30 heteroaryl group having at least one electron withdrawing functional group.

2. The n-type semiconductor of claim 1 , wherein L 1 , L 2 , and L 3 are independently a C1 to C30 alkylene group substituted with an electron withdrawing functional group, a C2 to C30 alkenylene group substituted with an electron withdrawing functional group, or a C2 to C30 alkynylene group substituted with an electron withdrawing functional group.

3. The n-type semiconductor of claim 1 , wherein the electron withdrawing functional group is a halogen, a C1 to C10 haloalkyl group, a cyano group (—CN), a cyano-containing group, a nitro group (—NO 2 ), a C1 to C10 carboxyl group, a C2 to C30 N-containing heteroaryl group, or a carbonyl group (—C(═O)R, wherein R is a C1 to C10 alkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group).

4. The n-type semiconductor of claim 1 , wherein the compound represented by Chemical Formula 1 is a compound represented by Chemical Formula 1-1:

wherein, in Chemical Formula 1-1,
X 1 , X 2 , and X 3 are CR a or N, wherein R a is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
L 1 , L 2 , and L 3 are independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, or a substituted or unsubstituted C2 to C30 alkynylene group that includes at least one linker selected from —NR b —, —C(═O)—, —S(═O)—, —OC(═O)—, —C(═O)O—, —S(═O) 2 —, —Si(R e R d ) 2 —, and —C(═O)NR e —,wherein, R b , R e , R d , and R e are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group,
EWG 1 , EWG 2 , and EWG 3 are an electron withdrawing functional group,
R 1 , R 2 , and R 3 are hydrogen, deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group,
a1, b1, and c1 are independently an integer of 1 to 3, and
a1+a2, b1+b2, and c1+c2 are independently an integer of less than or equal to 5.

5. The n-type semiconductor of claim 4 , wherein L 1 , L 2 , and L 3 are independently a C1 to C30 alkylene group substituted with an electron withdrawing functional group, a C2 to C30 alkenylene group substituted with an electron withdrawing functional group, or a C2 to C30 alkynylene group substituted with an electron withdrawing functional group.

6. The n-type semiconductor of claim 4 , wherein the electron withdrawing functional group is a halogen, a C1 to C10 haloalkyl group, a cyano group (—CN), a cyano-containing group, a nitro group (—NO 2 ), a C1 to C10 carboxyl group, a C2 to C30 N-containing heteroaryl group, or a carbonyl group (—C(═O)R, wherein R is a C1 to C10 alkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group.

7. The n-type semiconductor of claim 1 , wherein the compound represented by Chemical Formula 1 is a compound represented by Chemical Formula 1-2:

wherein in Chemical Formula 1-2,
X 1 , X 2 , and X 3 are CR a or N, wherein R a is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
L 1 , L 2 , and L 3 are independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, or a substituted or unsubstituted C2 to C30 alkynylene group that includes at least one linker selected from —NR b —, —C(═O)—, —S(═O)—, —OC(═O)—, —C(═O)O—, —S(═O) 2 —, —Si(R e R d ) 2 —, and —C(═O)NR e —,wherein, R b , R e , R d , and R e are independently hydrogen, deuterium, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group,
Y 11 , Y 12 , and Y 13 are independently CR f or N, wherein R f is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
R 1 is hydrogen, deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group, a is an integer of 0 to 2,
Y 21 , Y 22 , and Y 23 are independently CR g or N, wherein R g is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
R 2 is hydrogen, deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group, b is an integer of 0 to 2,
Y 31 , Y 32 , and Y 33 are independently CR h or N, wherein R h is hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C10 aryl group, or a C2 to C10 heteroaryl group,
R 3 is hydrogen, deuterium, a halogen, a cyano group, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C2 to C10 heteroalkyl group, a C6 to C14 aryl group, or a C2 to C10 heteroaryl group, c is an integer of 0 to 2, and
at least one of Y 11 , Y 12 , and Y 13 , Y 21 , Y 22 , and Y 23 , Y 31 , Y 32 and Y 33 is N.

8. The n-type semiconductor of claim 7 , wherein L 1 , L 2 , and L 3 are independently a C1 to C30 alkylene group substituted with an electron withdrawing functional group, a C2 to C30 alkenylene group substituted with an electron withdrawing functional group, or a C

Assignees

• Samsung Electronics Co Ltd
• Seoul Nat Univ R&Db Foundation

Inventors

• Choi Yeong Suk
• Park Soo Young
• Yun Sung Young
• Kim Hyeong-Ju
• Jung Seyoung
• Min Dong Joo
• Kwon Ji Eon

Classifications

• H10K30/451

  comprising a metal-semiconductor-metal [m-s-m] structure · CPC title

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07D213/57 Primary

  Nitriles · CPC title

• H10K85/211

  Fullerenes, e.g. C60 · CPC title

• H10K30/30

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