Phosphine-based compound and organic electroluminescence device including the same
A phosphine-based compound and an organic electroluminescence device including the same, the phosphine-based compound being represented by the following Formula 1:
1. A phosphine-based compound represented by the following Formula 1:
wherein, in Formula 1,
X 1 is O or S,
Ar 1 is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted pyrazinyl group,
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 2 and R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
“n 1 ” is an integer of 0 to 4, and
“n 2 ” and “n 3 ” are each independently an integer of 0 to 5.
2. The phosphine-based compound as claimed in claim 1 , wherein Ar 1 is a group represented by one of the following Formulae 2-1 to 2-4:
wherein, in Formulae 2-1 to 2-4,
R 4 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a combination thereof,
“n 4 ” is an integer of 0 to 4, and
“n 5 ” to “n 7 ” are each independently an integer of 0 to 3.
3. The phosphine-based compound as claimed in claim 2 , wherein:
Ar 1 is a group represented by Formula 2-1, and
the group represented by Formula 2-1 is a group represented by one of the following Formulae 2-1-1 to 2-1-3:
wherein, in Formulae 2-1-1 to 2-1-3, R 4 and “n 4 ” are defined the same as those of Formula 2-1.
4. The phosphine-based compound as claimed in claim 2 , wherein:
Ar 1 is a group represented by Formula 2-2, and
the group represented by Formula 2-2 is a group represented by one of the following Formulae 2-2-1 to 2-2-3:
wherein, in Formulae 2-2-1 to 2-2-3, R 5 and “n 5 ” are defined the same as those of Formula 2-2.
5. The phosphine-based compound as claimed in claim 2 , wherein:
Ar 1 is a group represented by Formula 2-3, and
the group represented by Formula 2-3 is a group represented by one of the following Formula 2-3-1 or 2-3-2:
wherein, in Formulae 2-3-1 and 2-3-2, R 6 and “n 6 ” are defined the same as those of Formula 2-3.
6. The phosphine-based compound as claimed in claim 2 , wherein R 4 to R 7 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a group represented by the following Formula 3, or a combination thereof,
wherein, in Formula 3,
X 2 is O or S,
R 8 and R 9 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and
“n 8 ” and “n 9 ” are each independently an integer of 0 to 5.
7. The phosphine-based compound as claimed in claim 1 , wherein R 1 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a group represented by the following Formula 4:
wherein, in Formula 4,
R 10 and R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and
“n 10 ” and “n 11 ” are each independently an integer of 0 to 5.
8. The phosphine-based compound as claimed in claim 1 , wherein the phosphine-based compound represented by Formula 1 is represented by the following Formula 5:
wherein, in Formula 5,
L 1 is a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted pyrimidylene group, or a substituted or unsubstituted pyrazinylene group,
X 4 is O or S,
R 12 to R 14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
“n 12 ” is an integer of 0 to 4,
“n 13 ” and “n 14 ” are each independently an integer of 0 to 5, and
X 1 , R 1 to R 3 , and “n 1 ” to “n 3 ” are defined the same as those of Formula 1.
9. The phosphine-based compound as claimed in claim 1 , wherein the phosphine-based compound represented by Formula 1 is represented by the following Formula 6:
wherein, in Formula 6,
X 5 is O or S,
L 2 is a direct linkage or a substituted or unsubstituted phenylene group,
R 15 and R 16 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
“n 15 ” and “n 16 ” are each independently an integer of 0 to 5,
“n 1 ” is an integer of 0 to 3, and
Ar 1 , X 1 , R 1 to R 3 , and “n 2 ” and “n 3 ” are defined the same as those of Formula 1.
10. The phosphine-based compound as claimed in claim 1 , wherein the phosphine-based compound represented by Formula 1 is a compound of the following Compound Group 1:
11. The phosphine-based compound as claimed in claim 1 , wherein the phosphine-based compound represented by Formula 1 is a compound of the following Compound Group 2:
12. The phosphine-based compound as claimed in claim 1 , wherein the phosphine-based compound represented by Formula 1 is a compound of the following Compound Group 3:
13. A phosphine-based compound represented by the following Formula 7:
wherein, in Formula 7,
X 6 is O or S,
Z 1 to Z 5 are each independently CR 20 or N, one or two of Z 1 to Z 5 being N,
R 17 and R 20 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a combination thereof,
R 18 and R 19 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
“n 17 ” is an integer of 0 to 4,
“n 18 ” and “n 19 ” are each independently an integer of 0 to 5, and
at least one of R 17 and R 20 is a group represented by the following Formula 8:
wherein, in Formula 8,
X 7 is O or S,
L 3 is a direct linkage or a substituted or unsubstituted phenylene group,
R 21 and R 22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and
“n 21 ” and “n 22 ” are each independently an integer of 0 to 5.
14. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region,
wherein at least one of the emission layer or the electron transport region includes a phosphine-based compound represented by the following Formula 1:
wherein, in Formula 1,
X 1 is O or S,
Ar 1 is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted pyrazinyl group,
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 2 and R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
“n 1 ” is an integer of 0 to 4, and
“n 2 ” and “n 3 ” are each independently an integer of 0 to 5.
15. The organic electroluminescence device as claimed in claim 14 , wherein:
the emission layer includes a host and a dopant, and
the host includes the phosphine-based compound represented by Formula 1.
16. The organic electroluminescence device as claimed in claim 14 , wherein:
the electron transport region includes:
an electron transport layer on the emission layer; and
an electron injection layer on the electron transport layer, and
the electron transport layer includes the phosphine-based compound represented by Formula 1.
17. The organic electroluminescence device as claimed in claim 14 , wherein:
the electron transport region includes:
a first electron transport layer on the emission layer while making contact with the emission layer;
a second electron transport layer on the first electron transport layer; and
an electron injection layer on the second electron transport layer, and
the first electron transport layer includes the phosphine-based compound represented by Formula 1.
18. The organic electroluminescence device as claimed in claim 14 , wherein Ar 1 is a group represented by one of the following Formulae 2-1 to 2-4:
wherein, in Formulae 2-1 to 2-4,
R 4 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a combination thereof,
“n 4 ” is an integer of 0 to 4, and
“n 5 ” to “n 7 ” are each independently an integer of 0 to 3.
19. The organic electroluminescence device as claimed in claim 14 , wherein the phosphine-based compound represented by Formula 1 is a compound of the following Compound Groups 1 to 3: