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

Patent metadata

Field	Value
Publication number	US-12501830-B2
Application number	US-202217857709-A
Country	US
Kind code	B2
Filing date	Jul 5, 2022
Priority date	Jul 29, 2021
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

A compound that may be applied to a sensor to improve electrical properties thereof is represented by Chemical Formula 1:

In Chemical Formula 1, each substituent is the same as defined in the detailed description.

First claim

What is claimed is:

1 . A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
X 1 and X 2 are different from each other and are each independently CR a R b , SiR c R d or NR e ,
R 2 to R 5 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, —NR f R g , or any combination thereof,
R a to R g are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R a and R b are each independently present or are linked to each other to form a ring,
R c and R d are each independently present or are linked to each other to form a ring,
R f and R g are each independently present or are linked to each other to form a ring, and
R 1 and R 6 are each —NR f R g , wherein R f and R g are each a substituted or unsubstituted C6 to C20 aryl group, and R f and R g are linked to each other through a single bond, a substituted or unsubstituted C1 to C5 alkylene group, a substituted or unsubstituted C2 to C5 alkenylene group, a substituted or unsubstituted C6 to C20 arylene group, O, S, Se, Te, CR h R i , SiR j R k , or GeR l R m to form a ring, wherein R h to R m are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof.

2 . The compound of claim 1 , wherein
X 1 is CR a R b or SiR c R d , wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and X 2 is NR e , wherein Re is a substituted or unsubstituted C6 to C20 aryl group.

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

wherein, in Chemical Formula 1A,
R a and R b are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

R e is a substituted or unsubstituted C6 to C20 aryl group, and
R 1 and R 6 are each one group of a set of groups listed in Group 1,

wherein, in Group 1,
Y 1 is O, S, Se, Te, CR h R i , SiR j R k or GeR l R m ,
R h to R q are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof,
n is an integer of 0 to 2, and
* is a linking point with Chemical Formula 1A.

4 . The compound of claim 1 , wherein
a glass transition temperature of the compound is about 170° C. to about 400° C., and a LUMO energy level of the compound is about 2.00 eV to about 2.80 eV.

5 . A sensor, the sensor comprising:
a first electrode and a second electrode; a photoelectric conversion layer between the first electrode and the second electrode; and a buffer layer between the first electrode and the photoelectric conversion layer, wherein the buffer layer includes a compound represented by Chemical Formula

wherein, in Chemical Formula 1,
X 1 and X 2 are different from each other and are each CR a R b , SiR c R d , or NR e ,
R 2 to R 5 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, —NR f R g , or any combination thereof,
R a to R g are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R a and R b are each independently present or are linked to each other to form a ring,
R c and R d are each independently present or are linked to each other to form a ring,
R f and R g are each independently present or are linked to each other to form a ring, and
R 1 and R 6 are each —NR f R g , wherein R f and R g are each a substituted or unsubstituted C6 to C20 aryl group, R f and R e are linked to each other through a single bond, a substituted or unsubstituted C1 to C5 alkylene group, a substituted or unsubstituted C2 to C5 alkenylene group, a substituted or unsubstituted C6 to C20 arylene group, O, S, Se, Te, CR h R i , SiR j R k , or GeR l R m to form a ring, wherein R h to R m are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof.

6 . The sensor of claim 5 , wherein
X 1 is CR a R b or SiR c R d , wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and X 2 is NR e , wherein R e is a substituted or unsubstituted C6 to C20 aryl group.

7 . The sensor of claim 5 , wherein the compound is represented by Chemical Formula 1A:

wherein, in Chemical Formula 1A,
R a and R b are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R e is a substituted or unsubstituted C6 to C20 aryl group, and
R 1 and R 6 are each one group of a set of groups listed in Group 1,

wherein, in Group 1,
Y 1 is O, S, Se, Te, CR h R i , SiR j R k , or GeR l R m ,
R h to R q are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a halogen, a cyano group, or any combination thereof,
n is an integer of 0 to 2, and
* is a linking point with Chemical Formula 1A.

8 . The sensor of claim 5 , further comprising:
a semiconductor substrate, wherein the semiconductor substrate includes circuitry that is electrically connected to the first electrode or the second electrode.

9 . A sensor-embedded display panel, comprising:
a substrate; a light emitting element on the substrate; and a sensor on the substrate, the sensor being in parallel with the light emitting element along an in-plane direction of the substrate such that the sensor and the light emitting element at least partially overlap in the in-plane direction, wherein the sensor includes
a first electrode and a second electrode,
a photoelectric conversion layer between the first electrode

Assignees

• Samsung Electronics Co Ltd
• Samsung Display Co Ltd

Inventors

• Hong Hye Rim
• Lim Seon-Jeong
• Heo Chul Joon
• Park Kyung Bae
• Yun Sung Young
• Choi Taejin

Classifications

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H10K65/00

  Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element and at least one organic radiation-sensitive element, e.g. organic opto-couplers (organic image sensors integrated with organic light-emitting devices H10K39/34; OLED displays integrated with photosensors H10K59/13) · CPC title

• H10K30/20

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

• H10K39/32

  Organic image sensors · 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