Organic electroluminescent device

1. An organic electroluminescent device comprising:

an anode;

a cathode; and

one or more organic material layers interposed between the anode and the cathode,

wherein said one or more organic material layers comprise (a) a light emitting layer comprising a host material and a dopant material, (b) a lifetime enhancement layer comprising a bipolar compound, (c) an electron transporting layer, and (d) at least one layer selected from the group consisting of a hole injection layer, a hole transporting layer, and an electron injection layer,

wherein the lifetime enhancement layer is interposed between the light emitting layer and the electron transporting layer,

wherein the bipolar compound has both an electron withdrawal group (EWG) moiety and an electron donor group (EDG) moiety, and satisfies the following (a) to (d) conditions:

(a) an ionization potential [Ip(LEL)] is 5.5 eV or more,

(b) E HOMO -E LUMO >2.9 eV,

(c) triplet energy is 2.3 eV or more, and

(d) ΔEst<0.5 eV (ΔEst indicates a difference between singlet energy and triplet energy of the compound)

wherein the EWG moiety in the bipolar compound comprises one or more moieties selected from the group consisting of the following chemical formulae:

wherein the EDG moiety in the bipolar compound a moiety in which the following Chemical Formula 1 and the following Chemical Formula 3 combine with each other to form a fused ring:

in Chemical Formula 1,

X 1 is selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ),

Y 1 to Y 4 are the same as or different from each other, and are each independently N or C(R 1 ), and in this case, a plurality of R 1 's is the same as or different from each other, and these groups optionally form a fused ring with an adjacent group,

X 2 and X 3 are the same as or different from each other, and are each independently N or C(R 2 ), and in this case, a plurality of R 2 's is the same as or different from each other, and these groups optionally form a fused ring with an adjacent group,

R 1 and R 2 and Ar 1 to Ar 5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino 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 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 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group, and

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the phosphine group, the phosphine oxide group, and the arylamine group of R 1 and R 2 and Ar 1 to Ar 5 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino 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 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group,

in Chemical Formula 3,

Y 5 to Y 14 are the same as or different from each other, and are each independently N or C(R 3 ), and in this case, a plurality of R 3 's is the same as or different from each other, and these groups optionally form a fused ring with Chemical Formula 1,

X 4 is selected from the group consisting of S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), and in this case, a plurality of Ar 1 's to Ar 5 's is the same as or different from each other,

a plurality of R 3 which does not form a fused ring, is the same as or different from each other, and is each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino 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 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 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group, and

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the phosphine group, the phosphine oxide group, and the arylamine group of R 3 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino 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 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group.

2. The organic electroluminescent device of claim 1 , wherein the light emitting layer is a blue fluorescence, a green fluorescence, or a red phosphorescence.

3. The organic electroluminescent device of claim 1 , wherein when the light emitting layer is a green phosphorescence, the bipolar compound comprised in the lifetime enhancement layer has triplet energy of 2.3 eV or more and an ionization potential of 6.0 eV or more.

4. The organic electroluminescent device of claim 1 , wherein when the light emitting layer is a blue phosphorescence, the bipolar compound comprised in the lifetime enhancement layer has triplet energy of 2.7 eV or more and an ionization potential of 6.0 eV or more.

5. The organic electroluminescent device of claim 1 , wherein a material for the electron transporting layer is the same as a material for the lifetime enhancement layer.

6. The organic electroluminescent device of claim 1 , wherein a material for the electron injection layer is the same as a material for the lifetime enhancement layer.

7. The organic electroluminescent device of claim 1 , wherein the electron injection layer or the electron transporting layer is provided by co-depositing alkali metal complexes.

8. The organic electroluminescent device of claim 1 , wherein an organic film layer blocking electrons and excitons is further provided between the hole transporting layer and the light emitting layer.

9. The organic electroluminescent device of claim 1 , wherein the light emitting layer comprises the dopant in a range of 0.1 wt % to 30 wt %.

10. The organic electroluminescent device of claim 1 , wherein a plurality of light emitting layers is sequentially laminated between the hole transporting layer and the electron transporting layer to implement a mixed color when voltage or current is applied thereto.

11. The organic electroluminescent device of claim 1 , wherein between the hole transporting layer and the electron transporting layer, a plurality of light emitting layers composed of homogeneous material is laminated, or a plurality of light emitting layers composed of heterogeneous materials is provided in series to implement a mixed color when voltage or current is applied thereto.

12. An organic electroluminescent device comprising:

an anode;

a cathode; and

one or more organic material layers interposed between the anode and the cathode,

wherein said one or more organic material layers comprise (a) a light emitting layer comprising a host material and a dopant material, (b) a lifetime enhancement layer comprising a bipolar compound, (c) an electron transporting layer, and (d) at least one layer selected from the group consisting of a hole injection layer, a hole transporting layer, and an electron injection layer,

wherein the lifetime enhancement layer is interposed between the light emitting layer and the electron transporting layer,

wherein the bipolar compound has both an electron withdrawal group (EWG) moiety and an electron donor group (EDG) moiety, and satisfies the following (a) to (d) conditions:

(a) an ionization potential [Ip(LEL)] is 5.5 eV or more,

(b) E HOMO -E LUMO >2.9 eV,

(c) triplet energy is 2.3 eV or more, and

(d) ΔEst<0.5 eV (ΔEst indicates a difference between singlet energy and triplet energy of the compound)

wherein the EWG moiety in the bipolar compound comprises one or more moieties selected from the group consisting of the following chemical formulae:

wherein the EDG moiety in the bipolar compound comprises a moiety represented by the following Chemical Formula 1g:

in Chemical Formula 1g,

X 1 and X 4 are the same as or different from each other, and each independently are selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), and in this case, a plurality of Ar 1 's to Ar 5 's is the same as or different from each other,

Y 1 to Y 4 are the same as or different from each other, and are each independently N or C(R 1 ), and in this case, a plurality of R 1 's is the same as or different from each other, and these groups optionally form a fused ring with an adjacent group,

Y 5 to Y 8 , and Y 11 to Y 14 are the same as or different from each other, and are each independently N or C(R 3 ), and in this case, a plurality of R 3 's is the same as or different from each other,

R 1 , R 3 and Ar 1 to Ar 5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino 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 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 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group, and

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the phosphine group, the phosphine oxide group, and the arylamine group of R 1 and R 3 and Ar 1 to Ar 5 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino 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 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 60 aryl boron group, a C 1 to C 40 phosphine group, a C 1 to C 40 phosphine oxide group, and a C 6 to C 60 arylamine group.