Compound, sensor, sensor embedded display panel, and electronic device

Patent metadata

Field	Value
Publication number	US-12439810-B2
Application number	US-202217979967-A
Country	US
Kind code	B2
Filing date	Nov 3, 2022
Priority date	Mar 24, 2022
Publication date	Oct 7, 2025
Grant date	Oct 7, 2025

Abstract

Disclosed are a compound represented by Chemical Formula 1, a sensor including the compound, a sensor-embedded display panel, and an electronic device.In Chemical Formula 1, X1, A, and R1 to R5 are as described 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 ,
A is a cyclic group comprising C═Z 1 , a halogen, 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 k R l , wherein R k and R l are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R k and R l are each independently present or linked to each other to form a ring,
R 1 to R 5 and R a to R h are each independently hydrogen, deuterium, 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
at least one of R 4 or R 5 is hydrogen, deuterium, a C1 to C5 alkyl group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C1 to C5 alkylthio group, or any combination thereof.

2. The compound of claim 1 , wherein R 4 and R 5 are each independently hydrogen, deuterium, a C1 to C5 alkyl group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C1 to C5 alkylthio group, or any combination thereof.

3. The compound of claim 2 , wherein R 4 and R 5 are each independently hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group.

4. The compound of claim 1 , wherein
one of R 4 or R 5 is hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group, and
another one of R 4 or R 5 is a substituted or unsubstituted phenyl group.

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

wherein, in Chemical Formulas 1A to 1E,
Z 1 to Z 3 are each independently O, S, Se, Te, or CR k R l , wherein R k and R l are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R k and R l are each independently present or linked to each other to form a ring,
Y is O, S, Se, or Te,
Ar 1 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,
R 10 to R 15 are each independently hydrogen, deuterium, 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 and 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.

6. The compound of claim 5 , wherein the cyclic group represented by Chemical Formula 1E is a cyclic group represented by one of Chemical Formulas 1EA to 1ED:

wherein, in Chemical Formulas 1EA to 1ED,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR k R l , wherein R k and R l are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R k and R l 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, deuterium, 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 ranging from 0 to 2, and
* is a linking point with Chemical Formula 1.

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 ,
Z 1 to Z 3 are each independently O, S, Se, Te, or CR k R l , wherein R k and R l are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R k and R l are each independently present or linked to each other to from a ring,
Y is O, S, Se, or Te,
Ar 1 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,
R 1 to R 5 , R 10 to R 15 and R a to R h are each independently hydrogen, deuterium, 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
at least one of R 4 or R 5 is hydrogen, deuterium, a C1 to C5 alkyl group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C1 to C5 alkylthio group, or any combination thereof.

8. A sensor, comprising
a first electrode,
a second electrode, and
a photoelectric conversion layer between the first electrode and the second electrode, the photoelectric conversion layer comprising the compound of claim 1 .

9. The sensor of claim 8 , wherein
one of the first electrode or the second electrode is a light-transmitting electrode,
another one of the first electrode or the second electrode is a reflective electrode,
the compound is a p-type semiconductor, and
the photoelectric conversion layer further comprises an n-type semiconductor forming a pn junction with the compound, the n-type semiconductor being a transparent semiconductor that does not substantially absorb light in a visible light wavelength spectrum.

10. An electronic device comprising the sensor of claim 8 .

11. A sensor-embedded display panel, comprising:
a substrate,
a light emitting element on the

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Tae Jin
• Hong Hyerim
• Park Kyung Bae
• Fang Feifei
• Yun Sungyoung
• Heo Chul Joon

Classifications

• H10K85/654

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

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K30/00

  Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation (integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20) · CPC title

• C07D421/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• H10K59/35

  comprising red-green-blue [RGB] subpixels · CPC title