Compound, organic photoelectronic device and image sensor
A compound is represented by Chemical Formula 1: X 1 -T-X 2 wherein T is a substituted or unsubstituted fused thiophene moiety, and each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group.
1. A compound represented by the following Chemical Formula 1:
X 1 -T-X 2 [Chemical Formula 1]
wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:
wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is 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 substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, a heterocyclic group including at least one of a nitrogen atom (N) and a sulfur atom (S), or a combination thereof, and
B is a substituted or unsubstituted C 6 to C 30 aryl group.
2. The compound of claim 1 , wherein
the alkenylene group links the substituted or unsubstituted fused thiophene moiety with the electron withdrawing group.
3. The compound of claim 1 , wherein the electron withdrawing group is selected from the following Group 1:
wherein each of R 11 to R 26 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.
4. The compound of claim 1 , wherein the compound is represented by one of the following Chemical Formulae 1a to 1c:
wherein, in the above Chemical Formulae 1a to 1c,
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group, and
each of R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.
5. A compound for selectively absorbing light in a green wavelength region and represented by the following Chemical Formula 1:
X 1 -T-X 2 [Chemical Formula 1]
wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:
wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is 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 substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, or a heterocylic group including at least one of a nitrogen atom (N) and a sulfur atom (S), and
B is a substituted or unsubstituted C 6 to C 30 aryl group.
6. The compound of claim 5 , wherein the compound has a maximum absorption wavelength (λ max ) of about 470 nm to about 580 nm.
7. An organic photoelectronic device comprising:
an anode and a cathode facing each other; and
an active layer between the anode and the cathode, the active layer including a compound represented by the following Chemical Formula 1:
X 1 -T-X 2 [Chemical Formula 1]
wherein, in the above Chemical Formula 1,
T is a substituted or unsubstituted fused thiophene moiety, and
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group,
wherein the fused thiophene moiety includes 3 to 7 thiophene rings, and
wherein the electron withdrawing group is an organic group represented by one of the following Chemical Formulae 2a to 2d:
wherein, in the above Chemical Formulae 2a to 2d,
each of R 11 to R 15 is independently one of hydrogen, a substituted or unsubstituted organic group, or a combination thereof,
Y is one of a sulfur atom (S) and an oxygen atom (O),
Z is 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 substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heterocyclic group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a cyano group, and a combination thereof,
A is a sulfur atom (S), an oxygen atom (O), a cyano group (CN)-containing group, a heterocyclic group including at least one of a nitrogen atom (N) and a sulfur atom (S), or a combination thereof, and
B is a substituted or unsubstituted C 6 to C 30 aryl group.
8. The organic photoelectronic device of claim 7 , wherein
the alkenylene group links the substituted or unsubstituted fused thiophene moiety with the electron withdrawing group.
9. The organic photoelectronic device of claim 7 , wherein the electron withdrawing group is selected from the following Group 1:
wherein each of R 11 to R 26 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.
10. The organic photoelectronic device of claim 7 , wherein the compound is represented by one of the following Chemical Formulae 1a to 1c:
wherein, in the above Chemical Formulae 1a to 1c,
each of X 1 and X 2 are independently an organic group including an alkenylene group and an electron withdrawing group, and
each of R 1 and R 2 are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, and a combination thereof.
11. The organic photoelectronic device of claim 7 , wherein the compound selectively absorbs light in a green wavelength region.
12. The organic photoelectronic device of claim 11 , wherein the green wavelength region has a maximum absorption wavelength (λ max ) of about 470 nm to about 580 nm.
13. The organic photoelectronic device of claim 7 , wherein the active layer further includes one of N,N′-dimethylquinacridone (DMQA), N,N′-dimethyl-2,9-dimethylquinacridone (DMMQA), a compound represented by the following Chemical Formula 3, and a combination thereof:
wherein, in the above Chemical Formula 3,
each of R a to R l are independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, and a combination thereof, and
X is an anion.
14. An image sensor comprising the organic photoelectronic device of claim 7 .
15. The image sensor of claim 14 , further comprising:
a semiconductor substrate integrated with a plurality of first photo-sensing device sensing light in a blue wavelength region and a plurality of second photo-sensing device sensing light in a red wavelength region;
a color filter layer on the semiconductor substrate, wherein the color filter layer includes a blue filter selectively absorbing light in a blue wavelength region and a red filter selectively absorbing light in a red wavelength region; and
the organic photoelectronic device on the color filter layer.