Organic electroluminescence device and polycyclic compound for organic electroluminescence device

1 . 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

the emission layer comprises a polycyclic compound represented by Formula 1:

wherein in Formula 1,

X 1 and X 2 are each independently O, S, or N(R 7 ),

e and f are each independently an integer from 0 to 4,

g is an integer from 0 to 2,

h is an integer from 0 to 3,

R 1 to R 4 , R 5-1 to R 5-3 , and R 6-1 to R 6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,

R 7 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or is combined with an adjacent group to form a ring, and

Y 1 and Y 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 6 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

at least one of Y 1 and Y 2 is a substituted or unsubstituted alkyl group of 6 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

2 . The organic electroluminescence device of claim 1 , wherein the emission layer emits delayed fluorescence.

3 . The organic electroluminescence device of claim 1 , wherein

the emission layer is a delayed fluorescence emission layer comprising a first compound and a second compound, and

the first compound comprises the polycyclic compound.

4 . The organic electroluminescence device of claim 1 , wherein the emission layer is a thermally activated delayed fluorescence emission layer emitting light having a wavelength in a range of about 430 nm to about 480 nm.

5 . The organic electroluminescence device of claim 1 , wherein

at least one of X 1 and X 2 is N(R 7 ), and

R 7 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

6 . The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 2-1 to Formula 2-5:

wherein in Formula 2-1 to Formula 2-5,

Ar 1-1 and Ar 1-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

R 1 to R 4 , R 5-1 to R 5-3 , R 6-1 to R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

7 . The organic electroluminescence device of claim 6 , wherein Ar 1-1 and Ar 1-2 are each independently a group represented by one of Formula 5-1 to Formula 5-3:

wherein in Formulae 5-1 to Formula 5-3,

R a1 to R a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,

m1, m3, and m5 are each independently an integer from 0 to 5,

m2 is an integer from 0 to 9,

m4 is an integer from 0 to 3, and

—* represents a binding site to a neighboring atom.

8 . The organic electroluminescence device of claim 1 , wherein at least one of R 5-1 to R 5-3 , and R 6-1 to R 6-3 is a substituted amine group.

9 . The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2:

wherein in Formulae 3-1 and Formula 3-2,

Ar 3-1 , Ar 3-2 , Ar 4-1 , and Ar 4-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, and

X 1 , X 2 , R 1 to R 4 , R 5-1 to R 5-3 , R 6-1 to R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

10 . The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 4:

wherein in Formula 4,

Ar 3-1 , Ar 3-2 , Ar 4-1 , and Ar 4-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, and

X 1 , X 2 , R 1 to R 4 , R 5-1 , R 5-3 , R 6-1 , R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

11 . The organic electroluminescence device of claim 10 , wherein Ar 3-1 , Ar 3-2 , Ar 4-1 , and Ar 4-2 are each independently a substituted or unsubstituted aryl group of 6 to 18 ring-forming carbon atoms.

12 . The organic electroluminescence device of claim 1 , wherein the polycyclic compound represented by Formula 1 is one selected from Compound Group 1:

13 . A polycyclic compound represented by Formula 1:

wherein in Formula 1,

X 1 and X 2 are each independently O, S, or N(R 7 ),

e and f are each independently an integer from 0 to 4,

g is an integer from 0 to 2,

h is an integer from 0 to 3,

R 1 to R 4 , R 5-1 to R 5-3 , and R 6-1 to R 6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,

R 7 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or is combined with an adjacent group to form a ring, and

Y 1 and Y 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 6 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

at least one of Y 1 and Y 2 is a substituted or unsubstituted alkyl group of 6 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

14 . The polycyclic compound of claim 13 , wherein

at least one of X 1 and X 2 is N(R 7 ), and

R 7 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

15 . The polycyclic compound of claim 13 , wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 2-1 to Formula 2-5:

wherein in Formula 2-1 to Formula 2-5,

Ar 1-1 and Ar 1-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

R 1 to R 4 , R 5-1 to R 5-3 , R 6-1 to R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

16 . The polycyclic compound of claim 15 , wherein Ar 1-1 and Ar 1-2 are each independently a group represented by one of Formula 5-1 to Formula 5-3:

wherein in Formulae 5-1 to Formula 5-3,

R a1 to R a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,

m1, m3, and m5 are each independently an integer from 0 to 5,

m2 is an integer from 0 to 9,

m4 is an integer from 0 to 3, and

—* represents a binding site to a neighboring atom.

17 . The polycyclic compound of claim 13 , wherein at least one of R 5-1 to R 5-3 , and R 6-1 to R 6-3 is a substituted amine group.

18 . The polycyclic compound of claim 13 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2:

wherein in Formulae 3-1 and Formula 3-2,

Ar 3-1 , Ar 3-2 , Ar 4-1 , and Ar 4-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, and

X 1 , X 2 , R 1 to R 4 , R 5-1 to R 5-3 , R 6-1 to R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

19 . The polycyclic compound of claim 13 , wherein the polycyclic compound represented by Formula 1 is represented by Formula 4:

wherein in Formula 4,

Ar 3-1 , Ar 3-2 , Ar 4-1 , and Ar 4-2 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, and

X 1 , X 2 , R 1 to R 4 , R 5-1 , R 5-3 , R 6-1 , R 6-3 , Y 1 , Y 2 , and e to h are the same as defined in connection with Formula 1.

20 . The polycyclic compound of claim 14 , wherein the polycyclic compound represented by Formula 1 is one selected from Compound Group 1: