Compound and sensor and sensor embedded display panel and electronic device

Patent metadata

Field	Value
Publication number	US-12358930-B2
Application number	US-202217839751-A
Country	US
Kind code	B2
Filing date	Jun 14, 2022
Priority date	Dec 20, 2021
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

A compound represented by Chemical Formula 1, a sensor including the compound, a sensor-embedded display panel including the compound, and an electronic device including the compound.

In Chemical Formula 1, X 1 , X 2 , X 3 , Ar 1 , L 1 , A, R 1 , and R 2 are the same as in the specification.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
Ar 1 is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a fused ring thereof,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
L 1 is (CR 3 R 4 ) n or R 5 C═CR 6 , wherein n is an integer of 1 to 3,
A is a cyclic group including C═Z 1 , a halogen, a C1 to C30 haloalkyl group, a cyano group, a dicyanovinyl group, or any combination thereof, wherein Z 1 is O, S, Se, Te, or CR q R r , R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
R 1 to R 6 and R a to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof, and
R 1 to R 6 and R a to R p are each independently present or adjacent two of R 1 to R 6 and R a to R p are linked to each other to form a ring.

2. The compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted 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 furan, a substituted or unsubstituted thiophene, a substituted or unsubstituted selenophene, a substituted or unsubstituted tellurophene, or a fused ring of two or more therefrom.

3. The compound of claim 1 , wherein
at least one of X 2 or X 3 is CR k R l , SiR m R n , or GeR o R p , and
R k to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof.

4. The compound of claim 1 , wherein A is a cyclic group represented by any one of Chemical Formulas 1A to 1E:

wherein, in Chemical Formulas 1A to 1E,
Ar 2 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a fused ring thereof,
Z 1 to Z 3 are each independently O, S, Se, Te, or CR q R r , wherein R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
Y is O, S, Se, or Te,
R 10 to R 15 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R 10 to R 15 are each independently present or adjacent two of R 10 to R 15 are linked to each other to form a ring, and
* is a linking point with Chemical Formula 1.

5. The compound of claim 4 , wherein the cyclic group represented by Chemical Formula 1A is represented by any one of Chemical Formulas 1AA to 1AD:

wherein, in Chemical Formulas 1AA to 1AD,
Z 1 and Z 2 are each independently O, S, Se, Te or CR q R r , wherein R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
G 1 and G 2 are each independently O, S, Se, or Te,
G 3 to G 6 are each independently N or CR 20 ,
R 16 to R 20 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R 16 to R 20 are each independently present or adjacent two of R 16 to R 20 are linked to each other to form a ring,
m is an integer of 0 to 2, and
* is a linking point with Chemical Formula 1.

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

wherein, in Chemical Formula 2 or 3,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
A is a cyclic group including C═Z 1 , a halogen, a C1 to C30 haloalkyl group, a cyano group, a dicyanovinyl group, or any combination thereof, wherein Z 1 is O, S, Se, Te, or CR q R r , R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof, and
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are each independently present or adjacent two of R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are linked to each other to form a ring.

7. The compound of claim 1 , wherein the compound is represented by any one of Chemical Formulas 1-1 to 1-5:

wherein, in Chemical Formulas 1-1 to 1-5,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
Ar 2 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsub

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lim Youn Hee
• Choi Taejin
• Fang Feifei
• Yi Jeoungin
• Park Kyung Bae
• Yun Sung Young

Classifications

• H10K85/621

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• H10K85/656

  comprising two or more different heteroatoms per ring (H10K85/652 takes precedence) · CPC title

• H10K85/654

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

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D471/06

  Peri-condensed systems · CPC title