Compound for organic photoelectric device and organic photoelectric device image sensor, and electronic device including the same
A compound for an organic photoelectric device includes at least one of a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2 and a combination thereof.
1. A compound for an organic photoelectric device comprising at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2:
wherein, in Chemical Formulae 1 and 2,
each of R 11 to R 14 are independently one of a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of R 21 , R 22 , R 31 , and R 32 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 30 alkyl group, and a combination thereof or are optionally linked to provide a Spiro structure with a fluorene ring,
each of R 23 , R 24 , R 33 , and R 34 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of Ar 1 , and Ar 2 are independently one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group that does not include a substituted or unsubstituted thiophene group, and a combination thereof,
Ar 3 is one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group, and a combination thereof,
each of p, p1, p2, q, q1, and q2 are independently an integer ranging from 0 to 3, and
each of m1 and m2 are 1.
2. The compound of claim 1 , wherein in Chemical Formula 1 or 2, at least one of R 11 to R 14 is a cyano group (—CN).
3. The compound of claim 1 , wherein in Chemical Formula 1 or 2, each of R 21 , R 22 , R 31 , and R 32 are independently one of a C 1 to C 30 alkyl group substituted with an aryl group and a C 1 to C 30 alkyl group substituted with a cycloalkyl group.
4. The compound of claim 1 , wherein in Chemical Formula 1 or 2, each of R 21 , R 22 , R 31 , and R 32 are independently a C 1 to C 30 alkyl group where a methylene group (—(CH 2 )—) that is not adjacent to a fluorene group is replaced by one of an arylene group and a cycloalkylene group.
5. The compound of claim 1 , wherein in Chemical Formula 1 or 2, at least two to four of R 11 to R 14 are a cyano group (—CN).
6. The compound of claim 1 , wherein in Chemical Formulae 1 and 2, each of Ar 1 , and Ar 2 is one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted thienothiophene group, and a combination thereof,
and Ar 3 is one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted thienothiophene group, and a combination thereof.
7. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 is a compound represented by one of Chemical Formulae 1-1 to 1-3:
wherein, in Chemical Formulae 1-1 to 1-3,
each of R 11 to R 14 are independently one of a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of R 21 and R 22 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 30 alkyl group, and a combination thereof or are optionally linked to provide a Spiro structure with a fluorene ring,
each of R 23 , R 24 , R 41 , and R 42 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of p and q are integers ranging from 0 to 3,
each of k1 and k2 correspond to the number of hydrogen in each aromatic ring, and
each of X 1 and X 2 are independently 0.
8. The compound of claim 7 , wherein in Chemical Formulae 1-1 to 1-3, at least one of R 11 to R 14 is a cyano group (—CN).
9. The compound of claim 7 , wherein in Chemical Formulae 1-1 to 1-3, at least two to four of R 11 to R 14 are a cyano group (—CN).
10. The compound of claim 1 , wherein the compound has a maximum absorption peak (λ max ) in a wavelength region in a thin film state of about 300 nm to about 720 nm.
11. The compound of claim 1 , wherein the compound shows a light absorption curve having a full width at half maximum (FWHM) in a thin film state of about 50 nm to about 150 nm.
12. The compound of claim 1 , wherein the compound is one of a p-type semiconductor compound and an n-type semiconductor compound.
13. The compound of claim 1 , wherein the compound has a bandgap of about 2.0 eV to about 4.0 eV.
14. The compound of claim 1 , wherein the compound has a LUMO level of about 2.0 eV to about 4.2 eV.
15. An organic 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, the active layer including the compound of claim 1 .
16. The organic photoelectric device of claim 15 , wherein in Chemical Formula 1 or 2, at least one of R 11 to R 14 is a cyano group (—CN).
17. The organic photoelectric device of claim 15 , wherein in Chemical Formula 1 or 2, at least two to four of R 11 to R 14 are a cyano group (—CN).
18. An image sensor comprising the organic photoelectric device of claim 15 .
19. The image sensor of claim 18 , further comprising:
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,
wherein the organic photoelectric device is on the semiconductor substrate and is configured to selectively absorb light in a green wavelength region.
20. The image sensor of claim 19 , further comprising:
a color filter layer between the semiconductor substrate and the organic photoelectric device, the color filter layer including a blue filter configured to selectively transmit light in a blue wavelength region and a red filter configured to selectively transmit light in a red wavelength region.
21. The image sensor of claim 19 , wherein at least two photo-sensing devices of the plurality of first photo-sensing devices and the plurality of second photo-sensing devices are stacked in a vertical direction on the semiconductor substrate.
22. The image sensor of claim 18 , wherein
the organic photoelectric device is a green photoelectric device, and
the green photoelectric device configured to selectively absorb light in a green wavelength region, 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 are stacked.
23. An electronic device comprising the image sensor of claim 18 .
24. A compound for an organic photoelectric device comprising at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2:
wherein, in Chemical Formulae 1 and 2,
each of R 11 to R 14 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof, provided that both R 11 and R 12 are not hydrogen and both R 13 and R 14 are not hydrogen,
each of R 21 , R 22 , R 31 , and R 32 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 30 alkyl group, and a combination thereof or are optionally linked to provide a spiro structure with a fluorene ring,
each of R 23 , R 24 , R 33 , and R 34 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of Ar 1 , and Ar 2 are independently one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group that does not include a substituted or unsubstituted thiophene group, and a combination thereof,
Ar 3 is one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group, and a combination thereof,
each of p, p1, p2, q, q1, and q2 are independently an integer ranging from 0 to 3,
each of m1 and m2 are 1, wherein
the compound represented by Chemical Formula 2 is a compound represented by Chemical Formulae 2-1 or Chemical Formula 2-2,
wherein, in Chemical Formulae 2-1 and 2-2,
each of R 11 to R 14 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof, provided that both R 11 and R 12 are not hydrogen and both R 13 and R 14 are not hydrogen,
each of R 21 , R 22 , R 31 , and R 32 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 30 alkyl group, and a combination thereof or are optionally linked to provide a Spiro structure with a fluorene ring,
each of R 23 , R 24 , R 33 , R 34 , and R 41 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of p1, p2, q1, and q2 are integers ranging from 0 to 3,
k1 corresponds to the number of hydrogen in each aromatic ring, and
each of X 1 and X 2 are independently one of S and 0.
25. The compound of claim 24 , wherein in Chemical Formulae 2-1 and 2-2, at least one of R 11 to R 14 is a cyano group (—CN).
26. The compound of claim 24 , wherein in Chemical Formulae 2-1 and 2-2, at least two to four of R 11 to R 14 are a cyano group (—CN).
27. An image sensor comprising:
an organic photoelectric device including a compound for the organic photoelectric device, the compound for the organic photoelectric device including at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2,
wherein, in Chemical Formulae 1 and 2,
each of R 11 to R 14 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof, provided that both R 11 and R 12 are not hydrogen and both R 13 and R 14 are not hydrogen,
each of R 21 , R 22 , R 31 , and R 32 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 30 alkyl group, and a combination thereof or are optionally linked to provide a spiro structure with a fluorene ring,
each of R 23 , R 24 , R 33 , and R 34 are independently one of hydrogen, a chloro group (—Cl), a bromo group (—Br), a substituted or unsubstituted C 1 to C 10 alkyl group, a cyano group (—CN), and a combination thereof,
each of Ar 1 , and Ar 2 are independently one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group that does not include a substituted or unsubstituted thiophene group, and a combination thereof,
Ar 3 is one of a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 3 to C 30 heteroarylene group, and a combination thereof,
each of p, p1, p2, q, q1, and q2 are independently an integer ranging from 0 to 3,
each of m1 and m2 are 1;
a semiconductor substrate integrated with a plurality of first photo-sensing devices configured to sense light in a blue wavelength region, a plurality of second photo-sensing devices configured to sense light in a red wavelength region, and a plurality of third photo-sensing devices configured to sense light in a green wavelength region,
wherein the organic photoelectric device is on the semiconductor substrate and is configured to selectively absorb light in a green wavelength region.
28. The image sensor of claim 27 , further comprising:
a color filter layer between the semiconductor substrate and the organic photoelectric device, the color filter including a blue filter configured to selectively transmit light in a blue wavelength region and a red filter configured to selectively transmit light in a red wavelength region.
29. The image sensor of claim 27 , wherein at least two photo-sensing devices selected from the first photo-sensing devices, the second photo-sensing devices and the third photo-sensing devices are stacked in a vertical direction on the semiconductor substrate.