Organic compound, light absorption sensor, sensor-embedded display panel, and electronic device
An organic compound is represented by Chemical Formula 1A or Chemical Formula 1B. In Chemical Formulas 1A and 1B, Ar 1 , Ar 2 , R 1 , R 2 , n, and m are each the same as in the detailed description.
1 . An organic compound represented by Chemical Formula 1A or Chemical Formula 1B:
wherein, in Chemical Formulas 1A and 1B,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C20 heteroaryl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, or any combination thereof, and
n and m are each independently an integer of 0 to 3.
2 . The organic compound of claim 1 , wherein
in Chemical Formula 1A, Ar 1 and Ar 2 are each independently afunctional group represented by one of Chemical Formulas 2A to 2K:
wherein, in Chemical Formulas 2A to 2K,
X 1 is O, S, Se, Te, S(═O), S(═O) 2 , NR a , SiR b R c , or GeR d R e , wherein R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, or any combination thereof,
Z 1 to Z 4 are each independently CR x or N, wherein R x is hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, or any combination thereof, provided that in Chemical Formula 2A, one of Z 1 to Z 4 is CR x wherein R x is a single bond, and in Chemical Formula 2I, one of Z 1 and Z 2 is CR x wherein R x is a single bond,
Ar 11 and Ar 12 are each independently a substituted or unsubstituted C6 to C20 arene group or a substituted or unsubstituted C2 to C20 heteroarene group,
at least one hydrogen of each aromatic ring or heteroaromatic ring is independently present or is replaced by deuterium, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C6 to C10 aryl group, a C6 to C10 aryloxy group, or any combination thereof, and
* is a linking point with Chemical Formula 1A.
3 . The organic compound of claim 2 , wherein
in Chemical Formula 1A, Ar 1 and Ar 2 are each independently afunctional group represented by one of Chemical Formulas 3A to 3I:
wherein, in Chemical Formulas 3A to 3I,
R a , R b , R b1 , R b2 , R c , R d , R e , and R f are each independently hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, or any combination thereof,
a is an integer from 0 to 3,
b, b1, and b2 are each independently an integer of 0 to 4,
c is an integer from 0 to 2, and
* is a linking point with Chemical Formula 1A.
4 . The organic compound of claim 1 , wherein
In Chemical Formula 1A, Ar 1 and Ar 2 are each independently a functional group represented by one of Chemical Formulas 3J to 3Y:
wherein, in Chemical Formulas 3J to 3Y,
X 1 and X 2 are each independently O, S, Se, Te, S(═O), S(═O) 2 , NR a , SiR b R c , or GeR d R e , wherein R a , R b , R c , R d , and R e are each independently hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, or any combination thereof,
Z 1 to Z 10 are each independently CR x or N, wherein R x is hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C14 aryl group, a C3 to C12 heteroaryl group, or any combination thereof, provided that when in Chemical Formula 3O, one of Z 1 to Z 6 is a linking point with Chemical Formula 1A, one of Z 1 to Z 6 is CR x wherein R x is a single bond; when in Chemical Formulas 3P, 3O, and 3S, one of Z 1 to Z 4 is a linking point with Chemical Formula 1A, one of Z 1 to Z 4 is CR x wherein R x is a single bond; when in Chemical Formula 3R, one of Z 5 to Z 6 is a linking point with Chemical Formula 1A, one of Z 5 and Z 6 is CR x wherein R x is a single bond; when in Chemical Formula 3T, one of Z 9 and Z 10 is a linking point with Chemical Formula 1A, one of Z 9 and Z 10 is CR x wherein R x is a single bond; when in Chemical Formula 3X and 3Y, Z 3 is a linking point with Chemical Formula 1A, Z 3 is CR x wherein R x is a single bond,
at least one hydrogen of each aromatic ring or heteroaromatic ring is independently present or is replaced by deuterium, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a C6 to C10 aryl group, a C6 to C10 aryloxy group, or any combination thereof, and
* is a linking point with Chemical Formula 1A.
5 . The organic compound of claim 1 , wherein
in Chemical Formula 1A, Ar 1 and Ar 2 are each independently a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenanthroyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzthiazolyl group, or a substituted or unsubstituted carbazolyl group.
6 . The organic compound of claim 1 , wherein
in Chemical Formula 1A, Ar 1 and Ar 2 are each independently a C10 to C30 aryl group substituted with an electron donating group or a C2 to C30 heteroaryl group substituted with an electron donating group.
7 . The organic compound of claim 1 , wherein
in Chemical Formulas 1A and 1B, R 1 and R 2 are each independently a functional group represented by Chemical Formula 4A or 4B:
wherein, in Chemical Formulas 4A and 4B,
a, b, and c are each independently an integer from 0 to 5 and d is 0 or 1,
R e in Chemical Formula 4B is a C1 to C10 alkyl group and e is an integer from 0 to 4, and
at least two methylene (—CH 2 —) groups that are not adjacent to each other are each independently present or are replaced by oxygen (—O—), sulfur (—S—), carbonyl (—C(═O)—), thionyl (—S(═O)—), or any combination thereof.
8 . The organic compound of claim 1 , wherein
the organic compound has a LUMO energy level of about 2.5 eV to about 4.5 eV.
9 . A light absorption sensor, comprising
a first electrode,
a second electrode, and
a photoelectric conversion layer between the first electrode and the second electrode, the photoelectric conversion layer comprising the organic compound of claim 1 .
10 . The light absorption sensor of claim 9 , wherein
the organic compound is an n-type semiconductor,
the photoelectric conversion layer further includes a p-type semiconductor forming a pn junction with the organic compound, and
the p-type semiconductor is a compound that is represented by Chemical Formula 5:
wherein, in Chemical Formula 5,
X 3 is O, S, Se, Te, S(═O), S(═O) 2 , SiR a R b , GeR c R d , or CR e R f , wherein R a , R b , R c , R d , R e , and R f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, wherein R a , R b , R c , R d , R e , and R f are each independently present or each pair of R a and R b , R c and R d , or R e and R f are linked to each other to form a spiro structure,
Ar 3a and Ar 3b are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, wherein the substituted or unsubstituted C6 to C30 aryl group or the substituted or unsubstituted C3 to C30 heteroaryl group are each independently present or are linked to each other to form a fused ring,
Ar 4 is a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a fused ring of a substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group,
R 3a , R 3b , and R 3c are each 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 halogen, a cyano group, or any combination thereof, wherein R 3b and R 3c are each independently present or two adjacent groups are linked to each other to form a ring, and
Ar 3b and R 3b are independently present or are linked to each other to provide a fused ring.
11 . An electronic device comprising the light absorption sensor of claim 9 .
12 . A sensor-embedded display panel, comprising:
a substrate,
a light emitting element on the substrate, the light emitting element including a light emitting layer, and
alight absorption sensor on the substrate, the light absorption sensor including a photoelectric conversion layer,
wherein the light emitting element and the light absorption sensor are arranged in parallel along an in-plane direction of the substrate such that the photoelectric conversion layer and the light emitting layer at least partially overlap in the in-plane direction, and
wherein the photoelectric conversion layer includes the organic compound of claim 1 .
13 . The sensor-embedded display panel of claim 12 , wherein
the organic compound is an n-type semiconductor,
the photoelectric conversion layer further includes a p-type semiconductor forming a pn junction with the organic compound, and
the p-type semiconductor is a compound that is represented by Chemical Formula 5:
wherein, in Chemical Formula 5,
X 3 is O, S, Se, Te, S(═O), S(═O) 2 , SiR a R b , GeR c R d , or CR e R f , wherein R a , R b , R c , R d , R e , and R f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, wherein R a , R b , R c , R d , R e , and R f are each independently present or each pair of R a and R b , R c and R d , or R e and R f are linked to each other to form a spiro structure,
Ar 3a and Ar 3b are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, wherein the substituted or unsubstituted C6 to C30 aryl group or the substituted or unsubstituted C3 to C30 heteroaryl group are each independently present or are linked to each other to form a fused ring,
Ar 4 is a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a fused ring of a substituted or unsubstituted C6 to C30 arene group and a substituted or unsubstituted C3 to C30 heteroarene group,
R 3a , R 3b , and R 3c are each 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 halogen, a cyano group, or any combination thereof, wherein R 3b and R 3c are each independently present or two adjacent groups are linked to each other to form a ring, and
Ar 3b and R 3b are independently present or are linked to each other to provide a fused ring.
14 . The sensor-embedded display panel of claim 12 , wherein the light emitting element includes a first light emitting element, a second light emitting element, and a third light emitting element, wherein the first light emitting element, the second light emitting element, and the third light emitting element are configured to emit light of different wavelength spectra, and
the light absorption sensor is configured to absorb light emitted from at least one of the first light emitting element, the second light emitting element, or the third light emitting element and reflected by a recognition target to the light absorption sensor and convert the absorbed light into an electrical signal.
15 . The sensor-embedded display panel of claim 12 , wherein
the sensor-embedded display panel further includes a first common auxiliary layer that is a single piece of material that extends continuously between the light emitting element and the substrate and between the light absorption sensor and the substrate.
16 . The sensor-embedded display panel of claim 12 , wherein the light emitting element and the light absorption sensor each include a separate portion of a common electrode configured to apply a common voltage to the light emitting element and the light absorption sensor, respectively, and
the sensor-embedded display panel further includes a second common auxiliary layer that is a single piece of material that extends continuously between the light emitting layer and the common electrode and between the photoelectric conversion layer and the common electrode.
17 . The sensor-embedded display panel of claim 16 , wherein a difference between a LUMO energy level of the second common auxiliary layer and a LUMO energy level of the organic compound is about 0 eV to about 1.2 eV.
18 . The sensor-embedded display panel of claim 12 , wherein
the sensor-embedded display panel includes
a display area configured to display a color, and
a non-display area excluding the display area, and
the light absorption sensor is in the non-display area.
19 . The sensor-embedded display panel of claim 18 , wherein
the light emitting element includes a first light emitting element configured to emit light of a red wavelength spectrum, a second light emitting element configured to emit light of a green wavelength spectrum, and a third light emitting element configured to emit light of a blue wavelength spectrum,
the display area includes
a plurality of first subpixels configured to display light of the red wavelength spectrum and comprise the first light emitting element,
a plurality of second subpixels configured to display light of the green wavelength spectrum and comprise the second light emitting element, and
a plurality of third subpixels configured to display light of the blue wavelength spectrum and comprise the third light emitting element, and
the light absorption sensor is between at least two subpixels selected from a first subpixel of the plurality of first subpixels, a second subpixel of the plurality of second subpixels, and a third subpixel of the plurality of third subpixels.
20 . An electronic device comprising the sensor-embedded display panel of claim 12 .