Quinacridone derivative, and photoactive layer and photoelectric conversion device including same
A quinacridone derivative may be represented by Chemical Formula 1, and a photoactive layer may include the same. A photoelectric conversion device may include a first electrode, a second electrode spaced apart from and configured to face the first electrode, and the photoactive layer including the quinacridone derivative between the first electrode and the second electrode.
1. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O), sulfur (S), and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group, wherein at least one of R 1 and R 2 is not hydrogen,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
2. The photoelectric conversion device of claim 1 , wherein the photoactive layer includes one selected from a p layer, an i layer, an n layer, and a combination thereof.
3. The photoelectric conversion device of claim 2 , wherein
the quinacridone derivative is a p-type material, and a material with a LUMO level lower than about −5.0 eV is an n-type material, and
the quinacridone derivative is included in one selected from the p layer, the i layer, and a combination thereof, and the n-type material is included in one selected from the i layer, the n layer, and a combination thereof.
4. The photoelectric conversion device of claim 2 , wherein
the quinacridone derivative is an n-type material, and a material with a LUMO level higher than −2.0 eV is a p-type material, and
the quinacridone derivative is included in one selected from the i layer, the n layer, and a combination thereof, and the p-type material is included in one selected from the p layer, the i layer, and a combination thereof.
5. The photoelectric conversion device of claim 1 , wherein the photoelectric conversion device includes a photodiode, a solar cell, an image sensing device, a photodetector, a photosensor, or an organic light emitting diode (OLED).
6. The photoelectric conversion device of claim 1 , wherein T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN) and a halogen,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O) and sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen, wherein at least one of R 1 and R 2 is not hydrogen,
w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
7. The photoelectric conversion device of claim 1 , wherein the quinacridone derivative includes one selected from compounds according to Chemical Formulas 2-7, 2-8 and a combination thereof:
8. The photoelectric conversion device of claim 1 , wherein the quinacridone derivative is represented by Chemical Formula 2-9:
9. The photoelectric conversion device of claim 1 , wherein the quinacridone derivative has a LUMO (lowest unoccupied molecular orbital) level ranging from about −2.0 eV to about −5.0 eV.
10. The photoelectric conversion device of claim 1 , wherein the quinacridone derivative has a bandgap ranging from about 1.5 eV to about 3.5 eV.
11. The photoelectric conversion device of claim 1 , wherein the quinacridone derivative has a maximum molar absorption coefficient of about 5.0×10 2 cm −1 ·M −1 to about 1.0×10 6 cm −1 ·M −1 .
12. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O), sulfur (S), and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 2 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
13. The photoelectric conversion device of claim 12 , wherein T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN) and a halogen,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O) and sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen, w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 2 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
14. The photoelectric conversion device of claim 12 , wherein the quinacridone derivative is represented by Chemical Formula 2-10:
15. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of sulfur (S) and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
16. The photoelectric conversion device of claim 15 , wherein T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN) and a halogen,
each of X 1 and X 2 are sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen,
w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
17. The photoelectric conversion device of claim 15 , wherein the quinacridone derivative includes one selected from compounds according to Chemical Formulas 2-5, 2-6 and a combination thereof:
18. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen, sulfur (S) and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3, wherein at least one of n1 and n2 is an integer ranging from 2 to 3,
m1 is an integer ranging from 1 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
19. The photoelectric conversion device of claim 18 , wherein T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN) and a halogen,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O) and sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen,
w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
m1 is an integer ranging from 1 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
20. The photoelectric conversion device of claim 18 , wherein the quinacridone derivative is represented by Chemical Formula 2-4:
21. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen, sulfur (S) and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
22. The photoelectric conversion device of claim 21 , wherein each of T 1 to T 4 are a halogen,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O) and sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen,
w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
n1 and n2 are each independently an integer ranging from 0 to 3, wherein at least one of n1 and n2 is an integer ranging from 2 to 3,
m1 is an integer ranging from 1 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
23. The photoelectric conversion device of claim 21 , wherein the quinacridone derivative is represented by Chemical Formula 2-9:
24. A photoelectric conversion device, comprising:
a first electrode;
a second electrode spaced apart from and configured to face the first electrode; and
a photoactive layer between the first electrode and the second electrode, the photoactive layer including a quinacridone derivative represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen, sulfur (S) and C(CN) 2 ,
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a cyano group (CN), a halogen, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 2 to C 30 heteroaryl group,
w1 and w2 are each independently an integer ranging from 0 to 5,
k1 and k2 are each independently an integer ranging from 1 to 4,
n1 and n2 are each independently an integer ranging from 0 to 3,
m1 is an integer ranging from 1 to 5, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of a substituted or unsubstituted C 2 to C 30 alkyl group, and a substituted or unsubstituted C 3 to C 30 cycloalkyl group.
25. The photoelectric conversion device of claim 24 , wherein T 1 to T 4 are one of same and different, and each of T 1 to T 4 are independently one of a cyano group (CN) and a halogen,
X 1 and X 2 are one of same and different, and each of X 1 and X 2 are independently one of oxygen (O) and sulfur (S),
R 1 to R 10 are one of same and different, and each of R 1 to R 10 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a cyano group (CN), and a halogen, wherein at least one of R 1 and R 2 is not a cyano group (CN),
w1 and w2 are each independently an integer of 0 or 1,
k1 and k2 are each independently an integer of 1 or 2,
n1 and n2 are each independently an integer ranging from 0 to 3, wherein at least one of n1 and n2 is an integer ranging from 2 to 3,
m1 is an integer ranging from 1 to 3, and
R 11 and R 12 are one of same and different, and each of R 11 and R 12 are independently one of a substituted or unsubstituted C 2 to C 10 alkyl group, and a substituted or unsubstituted C 3 to C 10 cycloalkyl group.
26. The photoelectric conversion device of claim 24 , wherein the quinacridone derivative is represented by Chemical Formula 2-3: