IP Library Granted Patent US 11,569,451
Granted Patent B2
US 11,569,451 · App. 17/475,688 · Granted Jan 31, 2023

Compound and photoelectric device, image sensor, and electronic device including the same

Inventors: Jisoo Shin (Seoul, KR); Yeong Suk Choi (Suwon-si, KR); Katsunori Shibata (Hwaseong-si, KR); Taejin Choi (Suwon-si, KR); Sungyoung Yun (Suwon-si, KR); Ohkyu Kwon (Seoul, KR); Sangmo Kim (Hwaseong-si, KR); Hiromasa Shibuya (Seongnam-si, KR); Gae Hwang Lee (Seongnam-si, KR); Yong Wan Jin (Seoul, KR); Hyesung Choi (Seoul, KR); Chul Baik (Suwon-si, KR); Hyerim Hong (Suwon-si, KR)
Assignee: Samsung Electronics Co., Ltd.
H01L51/0071C07D409/06C07D421/04C07D421/06C07D421/14C07F7/0816C07F7/30C07F11/00H01L27/307H01L51/0052H01L51/0061H01L51/0062H01L51/0077H01L51/0094H01L51/4253H01L51/0067H01L51/0068
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Quick Facts
Patent No.
US 11,569,451
App. No.
17/475,688
Granted
Jan 31, 2023
Kind
B2
Abstract

A compound of Chemical Formula 1, and a photoelectric device, an image sensor, and an electronic device including the same are disclosed: In Chemical Formula 1, each substituent is the same as defined in the detailed description.

Claims (63)

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 to R 3 are independently one of 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 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof,

R 1 and R 2 independently are present or linked with each other to provide a ring,

Ar 1 and Ar 2 are independently one of a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a combination thereof in a condensed ring,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond, wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2, and

Ar 3 is a cyclic group represented by Chemical Formula 2B,

wherein, in Chemical Formula 2B,

Y 2 is one of O, S, Se, Te, or C(R a )(CN), wherein R a is one of hydrogen, a cyano group (—CN), or a C1 to C10 alkyl group),

R 11 and R 12 are independently one of 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 a combination thereof, and

* is a linking point.

2. The compound of claim 1 , wherein in Chemical Formula 1, at least one of Ar 1 and Ar 2 includes a heteroatom at No. 1 position, and the heteroatom is one of nitrogen (N), sulfur (S), or selenium (Se).

3. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4A:

wherein, in Chemical Formula 4A,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond, wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R jj and R ii , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2, and

R 4a to R 4d and R 5a to R 5d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or

two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5a to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

4. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4B:

wherein, in Chemical Formula 4B,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2), and R 4a to R 4d and R 5b to R 5d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or

two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5b to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

5. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4C:

wherein, in Chemical Formula 4C,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2), and

R 4b b to R 4d and R 5b to R 5d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or

two adjacent groups of R 4b to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5b to R 5d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

6. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4D:

wherein, in Chemical Formula 4D,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one pair of R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2), and

R 4a to R 4d and R 5b and R 5d are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or

two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

7. The compound of claim 1 , wherein an electron donor moiety of the N-containing hetero aromatic ring in Chemical Formula 1 is represented by Chemical Formula 4E:

wherein, in Chemical Formula 4E,

G is one of —(CR d R e ) n —, —O—, —S—, —Se—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are independently one of hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, wherein R gg , R hh , R ii , R jj , R mm , and R nn are independently one of a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, and at least one of pair R gg and R hh , R ii and R jj , or R mm and R nn are linked with each other to provide a ring structure, and n in—(CR d R e ) n — is 1 or 2), and

R 4a to R 4d and R 5b and R 5e are independently one of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, or

two adjacent groups of R 4a to R 4d are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, or two adjacent groups of R 5b and R 5e are linked with each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring.

8. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength region of greater than or equal to about 5000 nm and less than or equal to about 600 nm.

9. The compound of claim 1 , wherein the compound exhibits a light absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 120 nm, in a thin film state.

10. The compound of claim 1 , wherein a difference between a melting point of the compound and a deposition temperature at which 10 wt % of an initial weight of the compound is lost is greater than or equal to about 3° C.

11. A photoelectric device, comprising

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

an active layer between the first electrode and the second electrode, wherein

the active layer includes the compound of claim 1 .

12. An image sensor comprising:

the photoelectric device of claim 11 .

13. The image sensor of claim 12 , wherein

the image sensor includes a semiconductor substrate and a photoelectric device on the semiconductor substrate,

the semiconductor substrate is 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 configured to selectively sense light in a green wavelength region, and

the photoelectric device is the photoelectric device of claim 11 .

14. The image sensor of claim 13 , further comprising:

a color filter layer on the semiconductor substrate, wherein

the color filter layer includes a blue filter and a red filter,

the blue filter is configured to selectively transmit light in a blue wavelength region, and

the red filter is configured to selectively transmit light in a red wavelength region.

15. The image sensor of claim 13 , wherein the first photo-sensing devices and the second photo-sensing devices are stacked in a vertical direction in the semiconductor substrate.

16. The image sensor of claim 12 , wherein

the photoelectric device is a green photoelectric device,

the image sensor includes a blue photoelectric device configured to selectively absorb light in a blue wavelength region,

the image sensor includes a red photoelectric device configured to selectively absorb light in a red wavelength region, and

the green photoelectric device, the blue photoelectric device, and the red photoelectric device are stacked.

17. An electronic device comprising:

the image sensor of claim 12 .

Priority Claims (2)
KR 10-2017-0136882 · Oct 20, 2017 · national
KR 10-2018-0125469 · Oct 19, 2018 · national
Continuity (2)
Division 16165005 · Oct 19, 2018
Related Publication 20220006025A1 · Jan 6, 2022
Cited By (1)
US 12,559,498