Organic electroluminescence device and monoamine 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 hole transport region includes a monoamine compound represented by at least one of the following Formulae 2 to 8:

wherein in Formula 2 to 8,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring 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, provided that when any one of Ar 1 and Ar 2 is 3-dibenzofuranyl, the other one of Ar 1 and Ar 2 is not 9-phenanthryl,

L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,

R 1 is 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 cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

a is an integer of 0 to 3,

m is an integer of 0 to 1, and

n is an integer of 0 to 6,

wherein in Formula 3,

i) when one of Ar 1 and Ar 2 is a naphthalene group or a phenyl group substituted with a naphthalene group and the other one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group,

the naphthalene group in the one of Ar 1 and Ar 2 is unsubstituted, or

the substituted or unsubstituted aryl group of the other one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 7 to 30 ring carbon atoms, and

ii) L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

wherein in Formula 4, a is an integer of 1 to 3,

wherein in Formula 6,

i) Ar 1 and Ar 2 are not dimethylfluorenyl groups,

ii) when any one of Ar 1 and Ar 2 is a p-biphenyl group and the other one of Ar 1 and Ar 2 includes an aryl substituent, the number of ring carbon atoms in the aryl substituent is 13 to 30,

iii) L is a phenylene group, a is an integer of 1 or more and 3 or less, and when L includes an m-phenylene group, Ar 1 and Ar 2 are not an unsubstituted or alkyl-substituted phenyl group, or an unsubstituted p-biphenyl group, and

vi) when Ar 1 and Ar 2 are each a heteroaryl group comprising S, or one of Ar 1 or Ar 2 is a heteroaryl group comprising S, and an other one of Ar 1 or Ar 2 is a heteroaryl group comprising O, the heteroaryl group comprising S is a substituted or unsubstituted dibenzothiophene group, and the heteroaryl group comprising O is a substituted or unsubstituted dibenzofuran group, and

wherein in Formula 7 and Formula 8,

i) Ar 1 and Ar 2 are not an unsubstituted p-biphenyl group or an unsubstituted p-terphenyl group,

ii) when Ar 1 and Ar 2 are a fluorene group or a fluorene derivative, Ar 1 and Ar 2 are substituents represented by Formula 7a;

wherein in Formula 7a,

R 3 is 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 cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and/or combine with each other to form a ring,

is an integer of 0 or more and 3 or less,

p is an integer of 0 or more and 4 or less,

iii) L is a substituted or unsubstituted phenylene group, and

vi) when one of Ar 1 and Ar 2 is an unsubstituted 2-dibenzofuran group, an unsubstituted 2-dibenzothiophene group, an unsubstituted 3-dibenzofuran group, or an unsubstituted 3-dibenzothiophene group, the other one of Ar 1 and Ar 2 is a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

2. The organic electroluminescence device as claimed in claim 1 , wherein L is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

3. The organic electroluminescence device as claimed in claim 2 , wherein L is a substituted or unsubstituted phenylene group.

4. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

5. The organic electroluminescence device as claimed in claim 4 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

6. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group having 5 to 12 ring carbon atoms.

7. The organic electroluminescence device as claimed in claim 6 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group.

8. The organic electroluminescence device as claimed in claim 1 , wherein R 2 is a hydrogen atom or a deuterium atom.

9. The organic electroluminescence device as claimed in claim 1 , wherein the hole transport region has a plurality of layers, and a layer of the plurality of layers contacting the emission layer includes the monoamine compound.

10. The organic electroluminescence device as claimed in claim 1 , wherein the hole transport region includes:

a hole injection layer on the first electrode;

a hole transport layer on the hole injection layer; and

an electron blocking layer on the hole transport layer, the electron blocking layer including the monoamine compound.

11. The organic electroluminescence device as claimed in claim 1 , wherein the electron transport region includes:

a hole blocking layer on the emission layer;

an electron transport layer on the hole blocking layer; and

an electron injection layer on the electron transport layer.

12. The organic electroluminescence device as claimed in claim 1 , wherein the monoamine compound is at least one selected from the group of compounds represented in the following Compound Groups 1 to 7:

[Compound Group 1]

[Compound Group 2]

[Compound Group 3]

[Compound Group 4]

[Compound Group 5]

[Compound Group 6]

[Compound Group 7]

13. A monoamine compound represented by at least one of the following Formulae 2 to 8:

wherein in Formula 2 to 8,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring 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, provided that when any one of Ar 1 and Ar 2 is 3-dibenzofuranyl, the other one of Ar 1 and Ar 2 is not 9-phenanthryl,

L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,

R 1 is 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 cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

a is an integer of 0 to 3,

m is an integer of 0 to 1, and

n is an integer of 0 to 6,

wherein in Formula 3, when one of Ar 1 and Ar 2 is a naphthalene group or a phenyl group substituted with a naphthalene group and the other one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group,

the naphthalene group in the one of Ar 1 and Ar 2 is unsubstituted, or

the substituted or unsubstituted aryl group of the one of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 7 to 30 ring carbon atoms,

wherein in Formula 4, a is an integer of 1 to 3,

wherein in Formula 6,

i) Ar 1 and Ar 2 are not dimethylfluorenyl groups,

ii) when any one of Ar 1 and Ar 2 is a p-biphenyl group and the other one of Ar 1 and Ar 2 includes an aryl substituent, the number of ring carbon atoms in the aryl substituent is 13 to 30,

iii) L is a phenylene group, a is an integer of 1 or more and 3 or less, and when L includes an m-phenylene group, Ar 1 and Ar 2 are not an unsubstituted or alkyl-substituted phenyl group, or an unsubstituted p-biphenyl group, and

vi) when Ar 1 and Ar 2 are each a heteroaryl group comprising S, or one of Ar 1 or Ar 2 is a heteroaryl group comprising S, and an other one of Ar 1 or Ar 2 is a heteroaryl group comprising O, the heteroaryl group comprising S is a substituted or unsubstituted dibenzothiophene group, and the heteroaryl group comprising O is a substituted or unsubstituted dibenzofuran group, and

wherein in Formula 7 and Formula 8,

i) Ar 1 and Ar 2 are not an unsubstituted p-biphenyl group or an unsubstituted p-terphenyl group,

ii) when Ar 1 and Ar 2 are a fluorene group or a fluorene derivative, Ar 1 and Ar 2 are substituents represented by Formula 7a;

wherein in Formula 7a,

R 3 is 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 cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or may combine with each other to form a ring,

is an integer of 0 or more and 3 or less,

p is an integer of 0 or more and 4 or less,

iii) L is a substituted or unsubstituted phenylene group, and

vi) when one of Ar 1 and Ar 2 is an unsubstituted 2-dibenzofuran group, an unsubstituted 2-dibenzothiophene group, an unsubstituted 3-dibenzofuran group, or an unsubstituted 3-dibenzothiophene group, the other one of Ar 1 and Ar 2 is a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

14. The monoamine compound as claimed in claim 13 , wherein L is a substituted or unsubstituted phenylene group.

15. The monoamine compound as claimed in claim 13 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

16. The monoamine compound as claimed in claim 13 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group having 5 to 12 ring carbon atoms.

17. The monoamine compound as claimed in claim 13 , wherein R 2 is a hydrogen atom or a deuterium atom.

18. The monoamine compound as claimed in claim 14 , wherein the monoamine compound is at least one selected from the group of compounds represented in the following Compound Groups 1 to 7:

[Compound Group 1]

[Compound Group 2]

[Compound Group 3]

[Compound Group 4]

[Compound Group 5]

[Compound Group 6]

[Compound Group 7]