Compound and sensor and sensor embedded display panel and electronic device
A compound represented by Chemical Formula 1, a sensor including the compound, a sensor-embedded display panel including the compound, and an electronic device including the compound. In Chemical Formula 1, X 1 , X 2 , X 3 , Ar 1 , L 1 , A, R 1 , and R 2 are the same as in the specification.
1. A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
Ar 1 is a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaromatic ring, or a fused ring thereof,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
L 1 is (CR 3 R 4 ) n or R 5 C═CR 6 , wherein n is an integer of 1 to 3,
A is a cyclic group including C═Z 1 , a halogen, a C1 to C30 haloalkyl group, a cyano group, a dicyanovinyl group, or any combination thereof, wherein Z 1 is O, S, Se, Te, or CR q R r , R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
R 1 to R 6 and R a to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof, and
R 1 to R 6 and R a to R p are each independently present or adjacent two of R 1 to R 6 and R a to R p are linked to each other to form a ring.
2. The compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted tetracene, a substituted or unsubstituted furan, a substituted or unsubstituted thiophene, a substituted or unsubstituted selenophene, a substituted or unsubstituted tellurophene, or a fused ring of two or more therefrom.
3. The compound of claim 1 , wherein
at least one of X 2 or X 3 is CR k R l , SiR m R n , or GeR o R p , and
R k to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof.
4. The compound of claim 1 , wherein A is a cyclic group represented by any one of Chemical Formulas 1A to 1E:
wherein, in Chemical Formulas 1A to 1E,
Ar 2 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a fused ring thereof,
Z 1 to Z 3 are each independently O, S, Se, Te, or CR q R r , wherein R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
Y is O, S, Se, or Te,
R 10 to R 15 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R 10 to R 15 are each independently present or adjacent two of R 10 to R 15 are linked to each other to form a ring, and
* is a linking point with Chemical Formula 1.
5. The compound of claim 4 , wherein the cyclic group represented by Chemical Formula 1A is represented by any one of Chemical Formulas 1AA to 1AD:
wherein, in Chemical Formulas 1AA to 1AD,
Z 1 and Z 2 are each independently O, S, Se, Te or CR q R r , wherein R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
G 1 and G 2 are each independently O, S, Se, or Te,
G 3 to G 6 are each independently N or CR 20 ,
R 16 to R 20 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof,
R 16 to R 20 are each independently present or adjacent two of R 16 to R 20 are linked to each other to form a ring,
m is an integer of 0 to 2, and
* is a linking point with Chemical Formula 1.
6. The compound of claim 1 , wherein the compound is represented by Chemical Formula 2 or 3:
wherein, in Chemical Formula 2 or 3,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
A is a cyclic group including C═Z 1 , a halogen, a C1 to C30 haloalkyl group, a cyano group, a dicyanovinyl group, or any combination thereof, wherein Z 1 is O, S, Se, Te, or CR q R r , R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof, and
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are each independently present or adjacent two of R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 to R 9 , and R a to R p are linked to each other to form a ring.
7. The compound of claim 1 , wherein the compound is represented by any one of Chemical Formulas 1-1 to 1-5:
wherein, in Chemical Formulas 1-1 to 1-5,
X 1 is Se, Te, SO, SO 2 , NR a , BR b , CR c R d , SiR e R f , or GeR g R h ,
X 2 and X 3 are each independently O, S, Se, Te, SO, SO 2 , NR i , BR j , CR k R l , SiR m R n , or GeR o R p ,
Ar 2 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a fused ring thereof,
Z 1 to Z 3 are each independently O, S, Se, Te or CR q R r , wherein R q and R r are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a carbonyl group, a cyano group, a dicyanovinyl group, or any combination thereof, and R q and R r are each independently present or linked to each other to form a ring,
Y is O, S, Se, or Te,
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 7 to R 15 , and R a to R p are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, or any combination thereof, and
R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 7 to R 15 , and R a to R p are each independently present or adjacent two of R 1 , R 2 , R 3a , R 3b , R 4a , R 4b , R 7 to R 15 , and R a to R p are linked to each other to form a ring.
8. A 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 including the compound according to claim 1 .
9. The sensor of claim 8 , wherein
the compound is a p-type semiconductor, and
the photoelectric conversion layer further comprises an n-type semiconductor forming a pn junction with the compound.
10. 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
a light 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 light absorption sensor and the light emitting element at least partially overlap in the in-plane direction, and
the photoelectric conversion layer includes the compound of claim 1 .
11. The sensor-embedded display panel of claim 10 , wherein
the light emitting element comprises first, second, and third light emitting elements, the first, second, and third light emitting elements configured to emit light of different wavelength spectrum in relation to each other, and
the light absorption sensor is configured to absorb light that is emitted from at least one of the first, second, or third light emitting elements and then reflected by a recognition target, and convert the light into an electrical signal.
12. The sensor-embedded display panel of claim 10 , wherein
the compound is a p-type semiconductor,
the photoelectric conversion layer further comprises an n-type semiconductor forming a pn junction with the compound, and
a difference between sublimation temperatures of the p-type semiconductor and the n-type semiconductor is less than or equal to 150° C., wherein each sublimation temperature of a given semiconductor of the p-type semiconductor or the n-type semiconductor is a temperature at which a weight loss of the given semiconductor of 10% compared to an initial weight of the given semiconductor occurs during thermogravimetric analysis of the given semiconductor at an ambient pressure of 10 Pa or less.
13. The sensor-embedded display panel of claim 12 , wherein the sublimation temperatures of the p-type semiconductor and the n-type semiconductor are 100° C. to 380° C., respectively.
14. The sensor-embedded display panel of claim 12 , wherein
the p-type semiconductor is a light absorbing material configured to absorb at least a portion of light in a visible light wavelength spectrum,
the n-type semiconductor is a transparent semiconductor configured not to substantially absorb light in the visible light wavelength spectrum.
15. The sensor-embedded display panel of claim 10 , further comprising a common electrode, the common electrode is configured to apply a common voltage to the light emitting element and the light absorption sensor.
16. The sensor-embedded display panel of claim 15 , further comprising:
a first common auxiliary layer that is a single piece of material that extends continuously between the light emitting element and the common electrode and between the light absorption sensor and the common electrode, and
a second common auxiliary layer that is another single piece of material that extends continuously between the light emitting element and the substrate and between the light absorption sensor and the substrate.
17. The sensor-embedded display panel of claim 10 , wherein
the sensor-embedded display panel comprises
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.
18. The sensor-embedded display panel of claim 17 , wherein
the light emitting element comprises 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 emission spectrum,
the display area comprises
a plurality of first subpixels configured to display red and comprising the first light emitting element,
a plurality of second subpixels configured to display green and comprising the second light emitting element, and
a plurality of third subpixels configured to display blue and comprising
the third light emitting element, and
the light absorption sensor is between at least two subpixels of a first subpixel of the plurality of first subpixels, a second subpixel of the plurality of second subpixels, or a third subpixel of the plurality of third subpixels.
19. An electronic device comprising the sensor of claim 8 .
20. An electronic device comprising the sensor-embedded display panel of claim 10 .