Organic compound and organic electroluminescent element comprising same
View Patent ↗The present disclosure relates to a novel compound and an organic electroluminescent element including the same, and the compound according to the present disclosure is used for an organic material layer of the organic electroluminescent element, thereby improving the light emitting efficiency, driving voltage, lifetime, and the like of the organic electroluminescent element.
1. A compound of the following Chemical Formula 1:
in Chemical Formula 1,
X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), wherein at least one of X 1 and X 2 is N(Ar 1 );
Y 1 to Y 12 are the same as or different from each other, and are each independently N or C(R 1 ), wherein when R 1 is present in a plural number, these are the same as or different from each other;
Ar 1 to Ar 5 are the same as or different from each other, and are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or optionally combine with an adjacent group to form a fused ring,
R 1 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or optionally combines with an adjacent group to form a fused ring, and
the alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of Ar 1 to Ar 5 and R 1 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, wherein the substituent optionally combines with an adjacent group to form a fused ring, provided that when the substituent is present in a plural number, these are optionally the same as or different from each other.
2. The compound of claim 1 , wherein the compound of the Chemical Formula 1 is represented by any one of the following Chemical Formulae 2 to 10:
in Chemical Formulae 2 to 10,
Ar 1 to Ar 5 and Y 1 to Y 12 are each the same as those defined in claim 1 .
3. The compound of claim 1 , wherein X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, and N(Ar 1 ), and in this case, at least one of X 1 and X 2 is N(Ar 1 ), and
Ar 1 is the same as that defined in claim 1 .
4. The compound of claim 1 , wherein Ar 1 to Ar 5 and R 1 are the same as or different from each other, and are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, and
the alkyl group, the aryl group, and the heteroaryl group of Ar 1 to Ar 5 and R 1 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, wherein the substituent optionally combines with an adjacent group to form a fused ring, provided that when the substituent is present in a plural number, these are optionally the same as or different from each other.
5. The compound of claim 1 , wherein Ar 1 to R 1 are each independently a substituent of the following Chemical Formula 11, or a C 6 to C 60 aryl group, and
the aryl group of Ar 1 and R 1 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, wherein the substituent optionally combines with an adjacent group to form a fused ring, provided that when the substituent is present in a plural number, these are optionally the same as or different from each other:
in Chemical Formula 11,
L is a single bond, or is selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Z 1 to Z 5 are the same as or different from each other, and are each independently N or C(R 11 ), provided that at least one of Z 1 to Z 5 is N, and in this case, when C(R 11 ) is present in a plural number, these are the same as or different from each other, and
R 11 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring,
wherein the alkyl group, the aryl group, the heteroaryl group, the arylamine group, the arylphosphine group, and the arylphospine oxide group of R 11 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, wherein when the substituent is present in a plural number, these are optionally the same as or different from each other.
6. The compound of claim 1 , wherein Ar 1 and R 1 are each independently a substituent represented by any one of the following Chemical Formulae A-1 to A-15:
in Chemical Formulae A-1 to A-15,
L is a single bond, or is selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
a plurality of R 11 is the same as or different from each other,
R 11 is selected from the group consisting of hydrogen, deuterium (D), halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring,
a plurality of R 12 is the same as or different from each other,
R 12 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring, and
n is an integer of 1 to 4,
wherein the alkyl group, the aryl group, the heteroaryl group, the arylamine group, the arylphosphine group, and the arylphospine oxide group of R 11 and R 12 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, wherein when the substituent is present in a plural number, these are optionally the same as or different from each other.
7. An organic electroluminescent element comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers comprises the compound described in claim 1 .
8. The organic electroluminescent element of claim 7 , wherein the one or more organic material layers comprise a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injection layer, and the one or more organic material layers comprising the compound are a light emitting layer or an electron transporting layer.
9. The organic electroluminescent element of claim 7 , wherein the one or more organic material layers comprise a hole injection layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injection layer, and the one or more organic material layers comprising the compound are a light emitting auxiliary layer.
10. The organic electroluminescent element of claim 7 , wherein the one or more organic material layers comprise a hole injection layer, a hole transporting layer, a light emitting layer, a lifetime enhancement layer, an electron transporting layer, and an electron injection layer, and the one or more organic material layers comprising the compound are a lifetime enhancement layer.
11. The organic electroluminescent element of claim 7 , wherein the compound of the Chemical Formula 1 is represented by any one of the following Chemical Formulae 2 to 10:
in Chemical Formulae 2 to 10,
Ar 1 to Ar 5 and Y 1 to Y 12 are each the same as those defined in claim 1 .
12. The organic electroluminescent element of claim 7 , wherein X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, and N(Ar 1 ), and in this case, at least one of X 1 and X 2 is N(Ar 1 ), and
Ar 1 is the same as that defined in claim 1 .
13. The organic electroluminescent element of claim 7 , wherein Ar 1 to Ar 5 and R 1 are the same as or different from each other, and are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, and
the alkyl group, the aryl group, and the heteroaryl group of Ar 1 to Ar 5 and R 1 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, wherein the substituent optionally combines with an adjacent group to form a fused ring, provided that when the substituent is present in a plural number, these are optionally the same as or different from each other.
14. The organic electroluminescent element of claim 7 , wherein Ar 1 to R 1 are each independently a substituent represented by the following Chemical Formula 11, or a C 6 to C 60 aryl group,
wherein the aryl group of Ar 1 and R 1 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, wherein the substituent optionally combines with an adjacent group to form a fused ring, provided that when the substituent is present in a plural number, these are optionally the same as or different from each other:
in Chemical Formula 11,
L is a single bond, or is selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Z 1 to Z 5 are the same as or different from each other, and are each independently N or C(R 11 ), provided that at least one of Z 1 to Z 5 is N, and in this case, when C(R 11 ) is present in a plural number, these are the same as or different from each other, and
R 11 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring,
wherein the alkyl group, the aryl group, the heteroaryl group, the arylamine group, the arylphosphine group, and the arylphospine oxide group of R 11 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, wherein when the substituent is present in a plural number, these are optionally the same as or different from each other.
15. The organic electroluminescent element of claim 7 , wherein Ar 1 and R 1 are each independently a substituent represented by any one of the following Chemical Formulae A-1 to A-15:
in Chemical Formulae A-1 to A-15,
L is a single bond, or is selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
a plurality of R 11 is the same as or different from each other,
R 11 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring,
a plurality of R 12 is the same as or different from each other,
R 12 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, or optionally combines with an adjacent group to form a fused ring, and
n is an integer of 1 to 4,
wherein the alkyl group, the aryl group, the heteroaryl group, the arylamine group, the arylphosphine group, and the arylphospine oxide group of R 11 and R 12 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium (D), halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 arylphosphine group, and a C 6 to C 40 arylphosphine oxide group, wherein when the substituent is present in a plural number, these are optionally the same as or different from each other.