Compound and photoelectric device, image sensor and electronic device including the same
A compound of Chemical Formula 1, and an organic 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.
1. A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1
Ar 1 is a substituted or unsubstituted C6 to C30 arene group or a substituted or unsubstituted C3 to C30 heteroarene group,
Ar 2 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group, a substituted or unsubstituted C6 to C30 heterocyclic group, or a fused ring thereof,
Ar 2 has at least one functional group selected from C═O, C═S, C═Se, and C═Te
X is Se, Te, SiR a R b , or GeR c R d (wherein R a , R b , R c , and R d are independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, and wherein R a , R b , R c , and R d are independently present or R a and R b or R c and R d are linked with each other to provide a spiro structure), and
R 1 to R 3 are 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 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and Re are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof.
2. The compound of claim 1 , wherein in Chemical Formula 1, R 1 is a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group.
3. The compound of claim 1 , wherein in Chemical Formula 1, Ar 1 is a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted indene, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted fluorine, or a substituted or unsubstituted acenaphthylene.
4. The compound of claim 1 , A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1, Ar 1 is a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted indole, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted carbazole, a substituted or unsubstituted phenazine, or a substituted or unsubstituted phenanthroline.
5. The compound of claim 1 , wherein in Chemical Formula 1, X is one of Se and Te.
6. The compound of claim 1 , wherein Are is a cyclic group represented by Chemical Formula 3:
[Chemical Formula 3]
wherein, in Chemical Formula 3,
Ar 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group,
Z 1 is O, S, Se, or Te, and
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group.
7. The compound of claim 1 , wherein in Chemical Formula 1, Are is a cyclic group represented by one of Chemical Formula 4A to Chemical Formula 4F:
wherein, in Chemical Formula 4A,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is 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 , R 13 , R 14 , and R 15 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl 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 a combination thereof, wherein R 11 , R 12 , R 13 , R 14 , and R 15 are independently present or at least one of R 12 and R 13 and R 14 and R 15 is linked with each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 4B,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,
Y 1 is O, S, Se, Te, or C(R a )(CN) (wherein R a is hydrogen, a cyano group (—CN), or a C1 to C10 alkyl group),
R 11 and R 12 are 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 a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 4C,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing group,
R 11 , R 12 , and R 13 are 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 a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 4D,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is 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 1 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 independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
R 11 , R 12 , and R 13 are 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 a combination thereof, wherein R 12 and R 13 are independently different and are linked with each other to provide a fused aromatic ring,
n is 0 or 1, and
* is a linking position,
wherein, in Chemical Formula 4E,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is a cyano group or a cyano-containing 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 independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
R 11 , R 12 , and R 13 are 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 a combination thereof, and
* is a linking position,
wherein, in Chemical Formula 4F,
Z 1 is O, S, Se, or Te,
Z 2 is O, S, Se, Te, or CR a R b , wherein R a and R b are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, provided that when Z 2 is CR a R b , at least one of R a and R b is 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 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 a combination thereof, and
G 3 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 independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group.
8. The compound of claim 1 , wherein the compound of Chemical Formula 1 is a compound represented by Chemical Formula 5A or 5B:
wherein, in Chemical Formula 5A,
Ar 2 , X, and R 1 to R 3 are the same as in Chemical Formula 1,
R x 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 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and R c are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof, and
m is an integer of 1 to 4,
wherein, in Chemical Formula 5B,
Ar 2 , X, and R 1 to R 3 are the same as in Chemical Formula 1,
R x and R y are 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 substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and R c are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof,
m is an integer of 1 to 4, and
n is an integer of 1 or 2.
9. The compound of claim 1 , wherein the compound of Chemical Formula 1 is a compound represented by Chemical Formula 5C or 5D:
wherein, in Chemical Formula 5C,
Ar 2 , X, and R 1 to R 3 are the same as in Chemical Formula 1, and
Y 1 to Y 4 are independently CR x R y or NR z (wherein R x , R y , and R z are 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 substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and Re are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof, provided that at least one of Y 1 to Y 4 is NR z ,
wherein, in Chemical Formula 5D,
Ar 2 , X, and R 1 to R 3 are the same as in Chemical Formula 1,
Y 1 to Y 4 are independently CR x R y or NR z (wherein R x , R y , and R z are 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 substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and R c are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group), or a combination thereof, provided that at least one of Y 1 to Y 4 is NR z , and
Y 5 and Y 6 are independently CR x R y or NR z (wherein R x , R y and R z are 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 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, —SiR a R b R c (wherein R a , R b , and R c are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group).
10. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) in a wavelength range of about 500 nm to about 600 nm in a thin film state.
11. 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 150 nm, in a thin film state.
12. The compound of claim 1 , wherein a difference between a melting point of the compound and a temperature at which 10 wt % of an initial weight is lost (deposition temperature) is greater than or equal to about 10° C.
13. 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 comprises the compound of claim 1 .
14. An image sensor comprising:
the photoelectric device of claim 13 .
15. The image sensor of claim 14 , wherein
the image sensor comprises a semiconductor substrate,
the photoelectric device is on the semiconductor substrate and selectively sensing light in a green wavelength region, and
the semiconductor substrate is integrated with a plurality of first photo-sensing devices sensing light in a blue wavelength region and a plurality of second photo-sensing devices sensing light in a red wavelength region.
16. The image sensor of claim 15 , further comprising:
a color filter layer comprising a blue filter selectively transmitting light in a blue wavelength region and a red filter selectively transmitting light in a red wavelength region.
17. The image sensor of claim 15 , wherein the first photo-sensing device and the second photo-sensing device are stacked in a vertical direction in the semiconductor substrate.
18. The image sensor of claim 14 , wherein
the photoelectric device is a green photoelectric device that is an organic photoelectric device,
the image sensor comprises a blue photoelectric device selectively absorbing light in a blue wavelength region and a red photoelectric device selectively absorbing light in a red wavelength region, and
the green photoelectric device, the blue photoelectric device, and the red photoelectric device are stacked.
19. An electronic device comprising:
the image sensor of claim 14 .