COMPOUND, PHOTOELECTRIC DEVICE, LIGHT ABSORPTION SENSOR, SENSOR EMBEDDED DISPLAY PANEL, AND ELECTRONIC DEVICE
Provided a compound represented by Chemical Formula 1, and a photoelectric device, a light absorption sensor, and an electronic device including the same. In Chemical Formula 1, the definition of each substituent is as described in the specification.
1 . A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a fused ring thereof,
G is —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —N═, —NR a —, —BR b —, —SiR c R d —, —SiR cc R dd —, —GeR e R f —, —GeR ee R ff —, —(CR g R h ) n1 —, —(CR gg R hh )—, —(C(R i ))═(C(R i ))—, or —(C(R ii ))═(C(R jj ))—, wherein R a , R b , R c , R d , R e , R f , R g , R h , R i , and R j are each independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C1 to C10 alkoxy group and each pair of R cc and R dd , R ee and R ff , R gg and R hh , or R ii and R jj are linked to each other to form a ring structure, and n1 of —(CR g R h ) n1 — is 1 or 2,
R x , R y , and R z are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen, or CN, x and y are each independently an integer of 1 or 2, z is an integer of 0 to 2, x+y+z is 4 or less,
R x and R y are present at para positions with respect to each other,
R 1 is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C6 to C30 aryl group, and
Ar 3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group of C═O, C═S, C═Se, C═Te, or C═CR p R q , a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group of C═O, C═S, C═Se, C═Te, or C═CR p R q , or a fused ring thereof, wherein R p and R q are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group.
2 . The compound of claim 1 , wherein
in Chemical Formula 1, R x , R y , and R z are each independently an electron donating group selected from a substituted or unsubstituted C1 to C30 alkyl group and a substituted or unsubstituted C1 to C30 alkoxy group.
3 . The compound of claim 1 , wherein
in Chemical Formula 1, G is —(CR g R h ) n1 — or —(CR gg R hh )—, wherein R g and R h are each independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group and R gg and R hh are linked to each other to provide a ring structure and n1 is 1 or 2, and R x and R y are present at para positions to each other.
4 . The compound of claim 1 , wherein
in Chemical Formula 1, at least one of Ar 1 or Ar 2 includes a heteroatom at a 1 st position and the heteroatom is one of nitrogen (N), sulfur (S), or selenium (Se).
5 . The compound of claim 1 , wherein
in Chemical Formula 1, a cyclic group that includes Ar 1 and Ar 2 is selected from moieties listed in Chemical Formula 2:
wherein, in Chemical Formula 2,
G is —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —N═, —NR a —, —BR b —, —SiR c R d —, —SiR cc R dd —, —GeR e R f —, —GeR ee R ff —, —(CR g R h ) n1 —, —(CR gg R hh )—, —(C(R i ))═(C(R i ))—, or —(C(R ii ))═(C(R jj ))—, wherein R a , R b , R c , R d , R e , R f , R g , R h , R i , and R j are each independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C1 to C10 alkoxy group and each pair of R cc and R dd , R ee and R f , R gg and R hh , or R ii and R jj are linked to each other to form a ring structure, and n1 of —(CR g R h ) n1 — is 1 or 2,
R 11 to R 14 and R 21 to R 24 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 (—CN), a cyano-containing group, or any combination thereof wherein R 11 to R 14 and R 21 to R 24 are independently present or two adjacent groups of R 11 to R 14 are linked to each other to provide a 5-membered aromatic ring group or a 6-membered aromatic ring group, or two adjacent groups of R 21 to R 24 are linked to each other to provide a 5-membered aromatic ring group or a 6-membered aromatic ring group, and
* is a linking point with Chemical Formula 1.
6 . The compound of claim 1 , wherein
in Chemical Formula 1, Ar 1 and Ar 2 are a C6 to C30 arene group unsubstituted with an electron withdrawing group represented by Ar 3 , a C3 to C30 heteroarene group unsubstituted with an electron withdrawing group represented by Ar 3 , or a condensed ring thereof.
7 . The compound of claim 1 , wherein
in Chemical Formula 1, the ring structure is a substituted or unsubstituted C5 to C30 hydrocarbon cyclic group or a substituted or unsubstituted C2 to C30 heterocyclic group.
8 . The compound of claim 1 , wherein
in Chemical Formula 1, the ring structure in Chemical Formula 1 includes a moiety represented by Chemical Formula 3:
wherein, in Chemical Formula 3,
Ar 33 and Ar 34 are each independently a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
* is a linking point with Chemical Formula 1.
9 . The compound of claim 1 , wherein
in Chemical Formula 1, each ring structure includes one of moieties represented by Chemical Formula 4:
wherein, in Chemical Formula 4,
X a and X b are each independently —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O) 2 —, —NR a1 —, —BR a2 —, —SiR b R c —, —SiR bb R cc —, —GeR d R e —, or —GeR dd R ee —, wherein R a1 , R a2 , R b , R c , R d , and R e are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 to C20 aryloxy group, or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of R bb and R cc or R dd and R ee is linked to each other to provide a ring structure,
L a is —O—, —S—, —Se—, —Te—, —NR a1 —, —BR a2 —, —SiR b R c —, —GeR d R e —, —(CR f R g ) n1 —, —(C(R P )═N))—, or a single bond, wherein R a1 , R a2 , R b , R c , R d , R e , R f , R g , and R P are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C6 to C20 aryloxy group, and n1 of —(CR f R g ) n1 — is 1 or 2,
at least one hydrogen of each ring structure is independently present or is replaced by at least one substituent selected from deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, and a substituted or unsubstituted C6 to C20 aryloxy group, and
* is a linking point with Chemical Formula 1.
10 . The compound of claim 9 , wherein
in Chemical Formula 4, a CH present in an aromatic ring of moiety (3), (4), (5), (6), (7), (8) or (9) is replaced by N.
11 . The compound of claim 1 , wherein
In Chemical Formula 1, Ar 3 is a cyclic group represented by Chemical Formula 5:
wherein, in Chemical Formula 5,
Ar 3 ′ is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, and
* is a linking point with Chemical Formula 1.
12 . The compound of claim 1 , wherein
in Chemical Formula 1, Ar 3 is a cyclic group represented by any one of Chemical Formulas 6A to 6G:
wherein, in Chemical Formula 6A,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
Z 3 is N or CR c , wherein R c is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group,
R 11 , R 12 , R 13 , R 14 , and R 15 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or any combination thereof, wherein R 11 , R 12 , R 13 , R 14 , and R 15 are each independently present or a pair of R 12 and R 13 or a pair of R 14 and R 15 is linked to each other to form an aromatic ring,
n is 0 or 1, and
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6B,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
Z 3 is O, S, Se, Te, or C(R a )(CN), wherein R a is hydrogen, a cyano group (—CN), or a C1 to C10 alkyl group,
R 11 and R 12 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 C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or any combination thereof, and
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6C,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
R 11 , R 12 , and R 13 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 C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), or any combination thereof,
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6D,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
Z 3 is N or CR c , wherein R c is hydrogen or a substituted or unsubstituted C 1 to C 10 alkyl group,
G 1 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R 11 , R 12 , and R 13 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 C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or any combination thereof, wherein R 12 and R 13 are independently present or a pair of R 12 and R 13 is linked to each other to provide an aromatic ring,
n is 0 or 1, and
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6E,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
Z 3 is N or CR c , wherein R c is hydrogen or a substituted or unsubstituted C 1 to C 10 alkyl group,
G 2 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R 11 , R 12 , and R 13 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 C4 to C30 heteroaryl group, a halogen, a cyano group, a cyano-containing group, or any combination thereof,
n is 0 or 1, and
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6F,
Z 1 and Z 2 are each independently O, S, Se, Te, or CR a R b , wherein R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
R 11 is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or any combination thereof,
G 3 is O, S, Se, Te, SiR x R y , or GeR z R w , wherein R x , R y , R z , and R w are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and
* is a linking point with Chemical Formula 1,
wherein, in Chemical Formula 6G,
R a and R b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group,
Z 1 to Z 4 are each independently O, S, Se, Te, or CR c R d , wherein R c and R d are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group, or a cyano-containing group, and
* is a linking point with Chemical Formula 1.
13 . The compound of claim 1 , wherein
the compound has a maximum absorption wavelength (λ max ) in a wavelength range of about 530 nm to about 555 nm in a thin film state, or
the compound exhibits an absorption curve having a full width at half maximum (FWHM) of about 50 nm to about 150 nm in a thin film state.
14 . A photoelectric device, comprising:
a first electrode and a second electrode facing each other, and
a light absorbing layer between the first electrode and the second electrode,
wherein the light absorbing layer includes the compound according to claim 1 .
15 . The photoelectric device of claim 14 , wherein
the light absorbing layer includes a p-type semiconductor and an n-type semiconductor,
wherein the p-type semiconductor includes the compound represented by Chemical Formula 1, and
the n-type semiconductor includes fullerene, a fullerene derivative, subphthalocyanine or a subphthalocyanine derivative, thiophene or a thiophene derivative or a compound represented by Chemical Formula 7:
wherein, in Chemical Formula 7,
X 5 and X 6 are each independently O or NR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, a cyano group, and
R 81 to R 84 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl 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.
16 . A light absorption sensor comprising the photoelectric device according to claim 14 .
17 . 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 and including a light absorbing layer and arranged in parallel with the light emitting layer along an in-plane direction of the substrate such that the light absorbing layer and the light emitting layer at least partially overlap in the in-plane direction,
wherein the light absorbing layer is configured to absorb light of a green wavelength spectrum, and
wherein the light absorbing layer includes the compound according to claim 1 .
18 . The sensor-embedded display panel of claim 17 , wherein
the light absorbing layer includes a p-type semiconductor and an n-type semiconductor,
the p-type semiconductor includes the compound according to claim 1 , and
the n-type semiconductor includes fullerene, a fullerene derivative, subphthalocyanine or a subphthalocyanine derivative, thiophene or a thiophene derivative or a compound represented by Chemical Formula 7:
wherein, in Chemical Formula 7,
X 5 and X 6 are each independently O or NR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a halogen, or a cyano group, and
R 81 to R 84 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl 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.
19 . An electronic device comprising the photoelectric device according to claim 14 .
20 . An electronic device comprising the sensor-embedded display panel according to claim 17 .