Compound for organic photoelectric device and organic photoelectric device, image sensor, and electronic device including the same
A compound is selected from the compound represented by Chemical Formula 1A, the compound represented by Chemical Formula 1B, and a mixture thereof.
1. A compound for an organic photoelectric device represented by the following Chemical Formula 1A or 1B:
wherein, in Chemical Formulae 1A and 1B,
each of R 1 to R 3 are independently one of hydrogen and a monovalent organic group,
a is an integer of 0 to 4, and
X is represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
R 4 is one of hydrogen and a monovalent organic group, and
R 5 and R 6 form a heteroatom-containing ring having electron withdrawing properties.
2. The compound of claim 1 , wherein the heteroatom-containing ring is one of substituents represented by the following Chemical Formulae 1a to 1e:
where * indicates a position bound to a methine group of Chemical Formula 2,
each of R a , R b , and R c are independently one of hydrogen and a monovalent organic group,
each of X 1 to X 10 are independently one of O and S,
each of Y 1 and Y 2 are independently one of S and CRR′ wherein each of R and R′ are independently one of hydrogen, CN, and a C 1 to C 10 alkyl group,
m is an integer of 1 to 3, and
n is an integer of 0 or 1.
3. The compound of claim 2 , wherein in Chemical Formulae 1A, 1B, and 1a to 1e, the monovalent organic group is one of a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, an amine group, a substituted or unsubstituted C 1 to C 30 alkylamine group, a substituted or unsubstituted C 6 to C 30 arylamine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C 6 to C 30 aryloxy group, a thiol group, a substituted or unsubstituted C 1 to C 30 alkylthio group, a substituted or unsubstituted C 6 to C 30 arylthio group, a cyano group, a cyano-containing group, a halogen, a halogen-containing group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted aminosulfonyl group, a substituted or unsubstituted arylsulfonyl group, and a combination thereof.
4. The compound of claim 2 , wherein in Chemical Formulae 1a to 1e, the monovalent organic group is one of a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 4 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, an amine group, a substituted or unsubstituted C 1 to C 30 alkylamine group, a substituted or unsubstituted C 6 to C 30 arylamine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C 6 to C 30 aryloxy group, a thiol group, a substituted or unsubstituted C 1 to C 30 alkylthio group, a substituted or unsubstituted C 6 to C 30 arylthio group, a cyano group, a cyano-containing group, a halogen, a halogen-containing group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted aminosulfonyl group, a substituted or unsubstituted arylsulfonyl group, and a combination thereof.
5. The compound of claim 1 , wherein the compound is represented by the following Chemical Formula 3A or Chemical Formula 3B:
wherein, in Chemical Formulae 3A and 3B,
each of R 1 to R 3 are independently one of hydrogen and a monovalent organic group,
a is an integer of 0 to 4,
each of R a , R b , and R c are independently one of hydrogen and a monovalent organic group,
m is an integer of 1 to 3, and
n is an integer of 0 or 1.
6. The compound of claim 1 , wherein the compound has a maximum absorption wavelength (λ max ) at about 500 nm to about 600 nm.
7. 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 100 nm.
8. The compound of claim 1 , wherein the compound is a p-type semiconductor compound.
9. The compound of claim 1 , wherein the compound has a higher melting point by about 50° C. or greater than a deposition temperature.
10. 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, wherein the active layer includes the compound of claim 1 .
11. The organic photoelectric device of claim 10 , wherein the active layer further comprises a n-type semiconductor compound.
12. The organic photoelectric device of claim 11 , wherein the n-type semiconductor compound is one of a sub-phthalocyanine, fullerene or a fullerene derivative, thiophene or a thiophene derivative, and a combination thereof.
13. The organic photoelectric device of claim 11 , wherein the active layer comprises the compound represented by Chemical Formula 1A, the compound represented by Chemical Formula 1B, or a mixture thereof.
14. The organic photoelectric device of claim 11 , wherein the active layer further comprises at least one of a p-type layer on one side of an intrinsic layer and a n-type layer on the other side of the intrinsic layer.
15. The organic photoelectric device of claim 11 , wherein the compound represented by Chemical Formula 1A or 1B is a first p-type semiconductor compound, and the active layer further comprises a second p-type semiconductor compound selectively absorbing green light.
16. An image sensor comprising the organic photoelectric device of claim 10 .
17. The image sensor of claim 16 , further comprising:
a semiconductor substrate 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, and
the organic photoelectric device on the semiconductor substrate is configured to selectively absorb light in a green wavelength region.
18. The image sensor of claim 17 , wherein the first photo-sensing devices and the second photo-sensing devices are stacked in a vertical direction on the semiconductor substrate.
19. The image sensor of claim 17 , further comprising:
a color filter layer between the semiconductor substrate and the organic photoelectric device, wherein the color filter layer includes a blue filter configured to selectively absorb light in a blue wavelength region and a red filter configured to selectively light in a red wavelength region.
20. The image sensor of claim 16 , wherein
the organic photoelectric device is a green photoelectric device, and
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 are stacked.
21. An electronic device comprising the image sensor of claim 16 .