IP Library Patent Application 18586047
Patent Application
App. No. 18/586,047

COMPOUND, PHOTOELECTRIC DEVICE, LIGHT ABSORPTION SENSOR, SENSOR EMBEDDED DISPLAY PANEL, AND ELECTRONIC DEVICE

Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US None
App. No.
18/586,047
Abstract

Provided is a compound represented by Chemical Formula 1 and having a reorganization energy of the compound of less than about 0.163 eV and a maximum absorption wavelength value calculated by density functional theory (DFT) of less than or equal to about 495 nm, and photoelectric devices, light absorption sensors, sensor-embedded display panels, and electronic devices including the same. In Chemical Formula 1, the definition of each substituent is as described in the specification.

Claims (111)

1 . A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

G 1 is a single bond, O, S, Se, Te, S(═O), S(═O) 2 , NR a , BR b , —SiR c R d —, —SiR cc R dd —, —GeR e R f —, —GeR ee R ff —, —(CR g R h ) n1 —, —(CR gg R hh )—, —(C(R i )═(C(R i ))—, or —(C(R ii )═(C(R ii ))—, wherein R a , R b , R c , R d , R e , R f , R g , R h , R i , and R j are each independently hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkoxy group, or a C6 to C20 aryl group, and each pair of R cc and R dd , R ee and R ff , R gg and R hh , or R ii and R jj is linked to each other to form a ring structure, and n1 of —(CR g R h ) n1 — is 1 or 2,

R x , R y , and R z are each independently hydrogen, deuterium, a halogen, a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkoxy group, or a C6 to C20 aryl group,

x is an integer of 0 to 4, and

y is an integer of 0 to 3, and

EWG is an acceptor moiety containing at least one electron withdrawing group,

wherein the compound has a reorganization energy of the compound that is less than about 0.163 eV, and the compound has a maximum absorption wavelength value calculated by density functional theory (DFT) that is less than or equal to about 495 nm.

2 . The compound of claim 1 , wherein

Chemical Formula 1 includes a carbazolyl ring group that includes a benzene ring, and

in Chemical Formula 1, at least one —CH═ of the benzene ring of the carbazolyl ring group is present or is replaced by —N═.

3 . The compound of claim 1 , wherein

Chemical Formula 1 includes a carbazolyl ring group, and

in Chemical Formula 1, nitrogen (N) is included at position 1 of the carbazolyl ring group.

4 . The compound of claim 1 , wherein

in Chemical Formula 1, R x , R y , and R z are each independently hydrogen or an electron donating group selected from a C1 to C10 alkyl group and a C1 to C10 alkoxy group.

5 . The compound of claim 1 , wherein

in Chemical Formula 1, the ring structure is a substituted or unsubstituted C5 to C30 hydrocarbon ring group or a substituted or unsubstituted C2 to C30 heterocyclic group.

6 . The compound of claim 1 , wherein

in Chemical Formula 1, the ring structure includes a moiety represented by Chemical Formula 2:

wherein, in Chemical Formula 2,

Ar 33 and Ar 34 are each independently a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and

* is a linking portion linked to Chemical Formula 1.

7 . The compound of claim 1 , wherein

in Chemical Formula 1, EWG is a substituted or unsubstituted C6 to C30 hydrocarbon ring group including at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═CR p R q , wherein R p and R q are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group; a substituted or unsubstituted C2 to C30 heterocyclic group including at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═CR p R q , wherein R p and R q are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group; or a fused ring thereof; or a C2 to C20 alkyl group including at least one functional group selected from C═O, C═S, C═Se, C═Te, and C═CR p R q , wherein R p and R q are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.

8 . The compound of claim 1 , wherein

in Chemical Formula 1, EWG is a cyclic group represented by Chemical Formula 4:

wherein, in Chemical Formula 4,

Ar′ is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, and

* is a linking portion linked to Chemical Formula 1.

9 . The compound of claim 1 , wherein

in Chemical Formula 1, EWG is a cyclic group represented by any one of Chemical Formula 5A to Chemical Formula 5H:

wherein, in Chemical Formula 5A,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

Z 3 is N or CR C , wherein R C is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,

R 11 , R 12 , and R 13 are each independently hydrogen, deuterium, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or any combination thereof, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5B,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

Z 3 is O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

R 11 and R 12 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or any combination thereof, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5C,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

R 11 , R 12 , and R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or any combination thereof, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5D,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

Z 3 is N or CR C , wherein R c is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,

G 2 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R 11 , R 12 , and R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or any combination thereof,

n is 0 or 1, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5E,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

Z 3 is N or CR C , wherein R C is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,

G 2 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R 11 , R 12 , and R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or any combination thereof,

n is 0 or 1, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5F,

Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

R 11 is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or any combination thereof,

G 2 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5G,

Z 1 is O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

R 11 , R 12 , and R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or any combination thereof, and

* is a linking portion linked to Chemical Formula 1,

wherein, in Chemical Formula 5H,

R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,

Z 1 to Z 4 are each independently O, S, Se, Te, or CR C R d , wherein R c and R d are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, and

* is a linking portion linked to Chemical Formula 1.

10 . The compound of claim 1 , wherein

the compound has a polarizability of less than or equal to about 500 bhor 3 .

11 . The compound of claim 1 , wherein

the compound has an oscillator strength value of greater than or equal to about 0.8.

12 . The compound of claim 1 , wherein

a dipole moment of the compound is greater than or equal to about 3 Debye.

13 . The compound of claim 1 , wherein

the compound has a maximum absorption wavelength (Amax) in a wavelength range of about 500 nm to about 540 nm in a thin film state.

14 . A photoelectric device, comprising:

a first electrode and a second electrode facing each other, and

a light absorbing layer between the first electrode and the second electrode,

wherein the light absorbing layer includes the compound of claim 1 .

15 . The photoelectric device of claim 14 , wherein

the light absorbing layer includes a p-type semiconductor and an n-type semiconductor,

the p-type semiconductor includes the compound represented by Chemical Formula 1, and

the n-type semiconductor includes fullerene, fullerene derivative, sub-phthalocyanine or a sub-phthalocyanine derivative, thiophene or a thiophene derivative, a compound represented by Chemical Formula 6, or any combination thereof:

wherein, in Chemical Formula 6,

X 5 and X 6 are each independently O or NR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, or a cyano group, and

R 81 to R 84 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy 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.

16 . A light absorption sensor comprising the photoelectric device of claim 14 .

17 . The light absorption sensor of claim 16 , wherein

the photoelectric device is a green photoelectric device configured to sense light in a green wavelength region,

the light absorption sensor further includes a semiconductor substrate integrated with a plurality of first photo-sensing devices configured to sense light in a blue wavelength region and a plurality of second photo-sensing devices configured to sense light in a red wavelength region, and

the photoelectric device is on the semiconductor substrate.

18 . The light absorption sensor of claim 16 , wherein

the photoelectric device is a green photoelectric device configured to sense light in a green wavelength region, and

the light absorption sensor includes a stack of

the green photoelectric device,

a blue photoelectric device configured to selectively absorb light in a blue wavelength region, and

a red photoelectric device configured to selectively absorb light in a red wavelength region.

19 . A sensor-embedded display panel, comprising:

a substrate,

a light emitting element on the substrate and including a light emitting layer, and

a light absorption sensor including a light absorbing layer on the substrate and arranged in parallel with the light emitting layer along an in-plane direction of the substrate such that the light absorption sensor and the light emitting layer at least partially overlap in the in-plane direction,

wherein the light absorbing layer is configured to absorb light of a red wavelength spectrum, a green wavelength spectrum, a blue wavelength spectrum, an infrared wavelength spectrum, or any combination thereof, and

wherein the light absorbing layer includes the compound according to claim 1 .

20 . An electronic device comprising the photoelectric device of claim 14 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2025
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 072342/0519 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2024
From: KIM, HYEONG-JU; PARK, KYUNG BAE; FANG, FEIFEI; YUN, SUNGYOUNG; YI, JEOUNG IN; LIM, YOUNHEE; CHOI, TAE JIN; HEO, CHUL JOON
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 066565/0796 →