Heterocyclic compound, and organic electroluminescence device and organic electroluminescence display device including the same
Provided are a heterocyclic compound represented by Formula 1 and an organic electroluminescence device and an organic electroluminescence display device including the heterocyclic compound represented by Formula 1 in an emission layer. In Formula 1, A is represented by Formula 2, D 1 is represented by Formula 3, and D 2 is represented by Formula 4.
1. A heterocyclic compound represented by the following Formula 1:
D 1 -A-D 2 Formula 1
wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:
wherein in Formulae 2 to 4,
q and r are each independently an integer of 0 to 3,
p is 0 or 1,
X 1 and X 2 are each independently CR′ or N,
R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,
Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
at least one of Y 1 or Y 2 is an electron-donating group,
in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:
wherein in Formula 5,
R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and
m is an integer of 0 to 6, and
wherein the heterocyclic compound emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm.
2. The heterocyclic compound of claim 1 , wherein p is 1, and X 1 and X 2 are N.
3. The heterocyclic compound of claim 1 , wherein at least one of Y 1 or Y 2 is represented by one of the above Formula 5, the following Formula 6 or the following Formula 7:
wherein in Formula 6,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
wherein in Formula 7,
Z is a direct linkage, O, S, or NR 8 ,
R 6 to R 8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
a and b are each independently an integer of 0 to 4.
4. The heterocyclic compound of claim 1 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.
5. The heterocyclic compound of claim 4 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.
6. The heterocyclic compound of claim 1 , wherein D 1 and D 2 are symmetric about A.
7. The heterocyclic compound of claim 6 , wherein X 1 and X 2 are the same.
8. The heterocyclic compound of claim 1 , wherein L 1 and L 2 are each independently represented by one of the following Formulae 8-1 to 8-4:
wherein in Formulae 8-2 and 8-3,
W 1 and W 2 are each independently NR 9 , S, or O, and
R 9 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.
9. The heterocyclic compound of claim 1 , wherein Y 1 and Y 2 are different from each other.
10. The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Formula 1 is one selected from compounds represented in the following Compound Group 1:
11. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region provided on the first electrode;
an emission layer provided on the hole transport region;
an electron transport region provided on the emission layer; and
a second electrode provided on the electron transport region,
wherein the emission layer comprises a heterocyclic compound represented by the following Formula 1:
D 1 -A-D 2 Formula 1
wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:
wherein in Formulae 2 to 4,
q and r are each independently an integer of 0 to 3,
p is 0 or 1,
X 1 and X 2 are each independently CR′ or N,
R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,
Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
at least one of Y 1 or Y 2 is an electron-donating group,
in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:
wherein in Formula 5,
R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and
m is an integer of 0 to 6,
wherein the emission layer comprises a host and a dopant and emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm, and
wherein the dopant comprises the heterocyclic compound.
12. The organic electroluminescence device of claim 11 , wherein p is 1, and X 1 and X 2 are N.
13. The organic electroluminescence device of claim 11 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.
14. The organic electroluminescence device of claim 11 , wherein D 1 and D 2 are symmetric about A.
15. The organic electroluminescence device of claim 11 , wherein the heterocyclic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1:
16. An organic electroluminescence display device, comprising:
a first pixel comprising a first organic light emitting diode which emits first visible rays;
a second pixel comprising a second organic light emitting diode which emits second visible rays;
a third pixel comprising a third organic light emitting diode which emits third visible rays; and
a fourth pixel comprising a fourth organic light emitting diode which emits near-infrared rays;
wherein the fourth organic light emitting diode comprises an emission layer comprising a heterocyclic compound represented by the following Formula 1:
D 1 -A-D 2 Formula 1
wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:
wherein in Formulae 2 to 4,
q and r are each independently an integer of 0 to 3,
p is 0 or 1,
X 1 and X 2 are each independently CR′ or N,
R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,
Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
at least one of Y 1 or Y 2 is an electron-donating group,
in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:
wherein in Formula 5,
R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and
m is an integer of 0 to 6.
17. The organic electroluminescence display device of claim 16 , wherein the fourth organic light emitting diode emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm.
18. The organic electroluminescence display device of claim 16 , wherein D 1 and D 2 are symmetric about A,
p is 1, X 1 and X 2 are N, and
at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.
19. The organic electroluminescence display device of claim 16 , wherein the heterocyclic compound represented by Formula 1 is at least one selected from compounds represented in the following Compound Group 1: