Organic electroluminescence device and spiro compound for organic electroluminescence device

1. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the emission layer comprises a spiro compound containing an aryl amine group and an indenoindole derivative and the emission layer emits green light,

wherein the emission layer comprises a host and a dopant, and the dopant comprises the spiro compound.

2. The organic electroluminescence device according to claim 1 , wherein, in the spiro compound, the indenoindole derivative and a pentagonal or hexagonal ring of the spiro compound form a spiro bond.

3. The organic electroluminescence device according to claim 1 , wherein the indenoindole derivative and the aryl amine group are bonded via a linker or via a direct linkage.

4. The organic electroluminescence device according to claim 1 , wherein the emission layer is a thermally activated delayed fluorescence emission layer.

5. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the emission layer comprises a spiro compound containing an aryl amine group and an indenoindole derivative and the emission layer emits green light, and

wherein the spiro compound has an absolute value of a difference between a singlet energy level and a triplet energy level of 0.2 eV or less.

6. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the emission layer comprises a spiro compound containing an aryl amine group and an indenoindole derivative and the emission layer emits green light, and

wherein the spiro compound is represented by the following Formula 1:

in Formula 1,

R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine 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, a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted cycloalkyl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycloalkyl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

Ar 1 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted cycloalkyl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycloalkyl group of 2 to 30 ring-forming carbon atoms,

Ar 2 and Ar 3 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,

L 1 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,

a is an integer of 0 to 3,

l is an integer of 0 to 4, and

Z 1 and Z 2 form spiro bonds of a ring compound represented by the following Formula 2:

in Formula 2,

X 1 is a direct linkage, O, S, CR 5 R 6 , SiR 7 R 8 , BR 9 , or NR 10 ,

X 2 to X 5 are each independently CR 11 R 12 ,

R 5 to R 12 are each independently 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 combined with an adjacent group to form a ring, and

* indicates a binding site to an adjacent atom of Formula 1.

7. The organic electroluminescence device according to claim 6 , wherein Formula 2 is represented by any one selected from among the following Formula 2-1 to Formula 2-7:

in Formula 2-1 to Formula 2-7,

R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine 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, a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted cycloalkyl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycloalkyl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

m and n are each independently an integer of 0 to 4,

R 5 to R 10 are the same as defined in Formula 2, and

* indicates a binding site to an adjacent atom of Formula 1.

8. The organic electroluminescence device according to claim 6 , wherein Formula 1 is represented by the following Formula 3:

in Formula 3,

R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine 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, a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, a substituted or unsubstituted cycloalkyl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycloalkyl group of 2 to 30 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

m and n are each independently an integer of 0 to 4, and

R 1 , R 2 , R 5 to R 10 , Ar 1 to Ar 3 , L 1 , X 1 , a, and l are the same as defined in Formula 1 and Formula 2.

9. The organic electroluminescence device according to claim 6 , wherein Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted triazinyl group.

10. The organic electroluminescence device according to claim 6 , wherein L 1 is a direct linkage.

11. The organic electroluminescence device according to claim 8 , wherein Formula 3 is represented by any one selected from among the following Formula 3-1 to Formula 3-5:

in Formulae 3-1 to 3-5,

R 1 to R 8 , Ar 1 to Ar 3 , L 1 , a, and l to n are the same as defined in Formula 3.

12. The organic electroluminescence device according to claim 6 , wherein the spiro compound represented by Formula 1 is any one selected from among compounds represented in the following Compound Group 1: