Polycyclic compound and organic electroluminescence device including the same
Provided are a polycyclic compound and an organic electroluminescence device including the same. The polycyclic compound according to an exemplary embodiment of the present disclosure is represented by the following formula 1. In Formula 1, X is O, SiR′R″, S, or BAr 1 . At least one of R 1 to R 8 is an aryl amine-containing electron donor. When X is O, SiR′R″, or S, the aryl amine-containing electron donor further includes a Si.
1. A polycyclic compound represented by the following Formula 1:
in Formula 1, X is O, SiR′R″, S, or BAr 1 ,
Ar 1 is substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
R′ and R″ are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, where R′ and R″ are optionally combined with each other to form a ring,
Ra to Re and R 1 to R 8 are each independently hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
when X is BAr 1 , at least one of R 1 to R 8 is represented by one of the following Formulae 2 to 4,
when X is O, SiR′R″, or S, at least one of R 1 to R 8 is represented by the following Formula 3 or 4:
in Formulae 2 to 4, Y is a direct linkage, CZ 1 Z 2 , NZ 3 , O, or S,
Z 1 to Z 3 and R 9 to R 44 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
optionally, R 25 and R 26 , R 43 and R 44 , and Z 1 and Z 2 each two groups independently combine with each other to form a ring, and
L 1 to L 3 are each independently a direct linkage, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring.
2. The polycyclic compound of claim 1 , wherein Formula 1 is represented by the following Formula 1-1:
in Formula 1-1, X and R 1 to R 8 are as defined in claim 1 .
3. The polycyclic compound of claim 1 , wherein L 1 to L 3 are each independently a direct linkage, or substituted or unsubstituted phenylene group.
4. The polycyclic compound of claim 1 , wherein Formula 3 is represented by one of the following Formulae 3-1 to 3-4:
in Formulae 3-1 to 3-4, L 2 , and R 17 to R 24 are as defined in claim 1 ,
E is hydrogen atom, deuterium, atom substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, where E optionally combines with an adjacent group to form a ring, and
n is an integer of 0 to 4.
5. The polycyclic compound of claim 1 , wherein Formula 4 is represented by one of the following Formulae 41 to 4-4:
in Formulae 4-1 to 4-4, L 3 , and R 27 to R 42 are as defined in claim 1 ,
Q is hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, Where Q optionally combines with an adjacent group to form a ring, and
m is an integer of 0 to 4.
6. The polycyclic compound of claim 1 , wherein X is BAr 1 , and Ar 1 is substituted or unsubstituted phenyl group.
7. The polycyclic compound of claim 1 , wherein Formula 1 is represented by the following Formula 1-2:
in Formula 1-2, Ra to Re, and R 1 to R 8 are as defined in claim 1 .
8. The polycyclic compound of claim 1 , wherein the polycyclic compound represented by Formula 1 is at least one of compounds represented in the following Compound Groups 1 and 3:
9. The polycyclic compound of claim 1 , wherein the polycyclic compound represented by Formula 1 is at least one of compounds represented in the following Compound Group 2:
10. 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 polycyclic compound represented by the following Formula 1:
in Formula 1, X is O, SiR′R″, S, or BAr 1 ,
Ar 1 is substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
R′ and R″ are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
Ra to Re, and R 1 to R 8 are each independently hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
when X is BAr 1 , at least one of R 1 to R 8 is represented by one of the following Formulae 2 to 4,
when X is O, SiR′R″, S, at least one of R 1 to R 8 is represented by the following Formula 3 or 4:
in Formulae 2, Y is a direct linkage, CZ 1 Z 2 , NZ 3 , O, or S,
Z 1 to Z 3 , and R 9 to R 44 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
optionally, R 25 and R 26 , R 43 and R 44 , and Z 1 and Z 2 each two groups independently combine with each other to form a ring, and
L 1 to L 3 are each independently a direct linkage, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring.
11. The organic electroluminescence device of claim 10 , wherein the polycyclic compound represented by Formula 1 has an absolute value of about 0.2 eV or less energy gap between a singlet energy level and a triplet energy level.
12. The organic electroluminescence device of claim 10 , wherein the polycyclic compound represented by Formula 1 is a material for emitting thermally activated delayed fluorescence.
13. The organic electroluminescence device of claim 10 , Wherein Formula 1 is represented by the following Formula 1-1:
in Formula 14, X, and R 1 to R 8 are as defined in claim 10 .
14. The organic electroluminescence device of claim 10 , wherein L 1 to L 3 are each independently a direct linkage, or substituted or unsubstituted phenylene group.
15. The organic electroluminescence device of claim 10 , wherein Formula 3 is represented by one of the following Formulae 3-1 to 3-4:
in Formulae 3-1 to 3-4, L 2 , and R 17 to R 24 are as defined in claim 10 ,
E is hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, where E optionally combines with an adjacent group to form a ring, and
n is an integer of 0 to 4.
16. The organic electroluminescence device of claim 10 , wherein Formula 4 is represented by one of the following Formulae 4-1 to 4-2:
in Formulae 4-1 to 4-4, L 3 , and R 27 to R 42 are as defined in claim 10 ,
Q is hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, where Q optionally combines with an adjacent group to form a ring, and
m is an integer of 0 to 4.
17. The organic electroluminescence device of claim 10 , wherein X is BAr 1 , and Ar 1 is substituted or unsubstituted phenyl group.
18. The organic electroluminescence device of claim 10 , wherein Formula 1 is represented by the following Formula 1-2:
in Formula 1-2, Ra to Re, and R 1 to R 8 are as defined in claim 10 .
19. The organic electroluminescence device of claim 10 , wherein the polycyclic compound represented by Formula 1 is at least one of compounds represented in the following Compound Groups 1 and 3:
20. The organic electroluminescence device of claim 10 , wherein the polycyclic compound represented by Formula 1 is at least one of compounds represented in the following Compound Group 2:
[Compound Group 2]
21. 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 polycyclic compound represented by the following Formula 1:
in Formula 1, X is O, SiR′R″, S, or BAr 1 ,
Ar 1 is substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
R′ and R″ are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
Ra to Re, and R 1 to R 8 are each independently hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
at least one of R 1 to R 8 is represented by the following Formula 2:
when X is BAr 1 in Formulae 2, Y is a direct linkage, CZ 1 Z 2 , NZ 3 , SiZ 4 Z 5 , O, S or CZ 6 Z 7 of which Z 6 and Z 7 combine with each other through Si to form a ring,
when X is O, SiR′R″, or S, Y is SiZ 4 Z 5 , or CZ 6 Z 7 of which Z 6 and Z 7 combine with each other through Si to form a ring,
Z 1 to Z 5 , and R 9 to R 16 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
Z 6 and Z 7 are each independently substituted or unsubstituted phenyl group,
optionally, Z 1 and Z 2 , and Z 4 and Z 5 each two groups independently combine with each other to form a ring, and
L 1 is a direct linkage, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring.
22. The organic electroluminescence device of claim 21 , wherein Formula 2 is represented by the following Formula 3 or 4:
in Formulae 3 and 4, R 17 to R 44 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
optionally, R 25 and R 26 , and R 43 and R 44 each two groups independently combine with each other to form a ring, and
L 2 and L 3 are each independently a direct linkage, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring.
23. The organic electroluminescence device of claim 21 , wherein the polycyclic compound represented by Formula 1 is a material for emitting thermally activated delayed fluorescence with wavelength from about 440 nm to about 460 nm.