KR20220000878A - Organic electro luminescence device - Google Patents

Abstract

The present invention relates to an organic electroluminescence device. The organic electroluminescence includes: an anode; a cathode; and one or more organic material layers interposed between the anode and the cathode and containing a light emitting layer and an electron transport layer. The electron transport layer includes a first electron-transport organic compound and a second electron-transport organic compound. At least one of the first electron-transport organic compound and the second electron-transport organic compound has a triplet energy of 2.0 eV or more.

Description

Organic electroluminescent device {ORGANIC ELECTRO LUMINESCENCE DEVICE}

The present invention relates to an organic electroluminescent device exhibiting a low driving voltage, high luminous efficiency and long life.

In general, when a current or voltage is applied to two electrodes in an organic electroluminescent device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected hole and electron meet, an exciton is formed, and the exciton falls to the ground state and emits light. In this case, the organic material layer may be classified into a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer according to their functions.

Here, the electron transport layer easily moves the electrons injected from the cathode or the electron injection layer to the light emitting layer, and is formed of a material with high electron mobility and easy electron injection. For example, Al complexes of 8-hydroxyquinoline; Li complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} hydroxyflavone-metal complexes and the like. However, since the material constituting the conventional electron transport layer contains a metal, it has high reactivity with oxygen, and thus oxidation is easy to occur, which reduces the lifespan of the organic electroluminescent device.

The present invention has been devised to solve the above problems, and an object of the present invention is to provide an organic electroluminescent device exhibiting a low driving voltage, high luminous efficiency and long lifespan.

The present invention is a positive electrode; cathode; and one or more organic material layers interposed between the anode and the cathode and including a light emitting layer and an electron transport layer, wherein the electron transport layer includes a first electron transporting organic compound and a second electron transporting organic compound different from each other , At least one of the first electron transporting organic compound and the second electron transporting organic compound provides an organic electroluminescent device, characterized in that the triplet energy is 2.0 eV or more.

The present invention mixes two or more different electron transporting organic compounds to form an electron transport layer of an organic electroluminescent device, at least one of which includes a compound having a triplet energy level of 2.0 eV or more, triplet energy level It has better characteristics such as driving voltage, luminous efficiency and lifespan compared to the conventional organic electroluminescent device that does not contain an electron-transporting organic compound of 2.0 eV or more. Therefore, when the organic electroluminescent device of the present invention is applied to a display panel, the performance and lifespan of the display panel can be improved.

1 is a cross-sectional view showing an organic electroluminescent device according to an embodiment of the present invention.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

The present inventors have found that when two or more different types of electron-transporting organic compounds are used as the electron-transporting layer material, the lifespan of the organic light-emitting device can be improved without a dopant such as a metal complex. In addition, when the triplet energy of at least one of the electron-transporting organic compounds is 2.0 eV or more, the electrons injected from the cathode or the electron injection layer are moved to the light-emitting layer, and excitons formed in the light-emitting layer can be prevented from diffusing into the electron-transporting layer. found out that there is

Accordingly, the present invention mixes a first electron-transporting organic compound and a second electron-transporting organic compound as an electron-transporting layer material of an organic electroluminescent device, and at least one of the first electron-transporting organic compound and the second electron-transporting organic compound It is characterized in that the triplet energy is 2.0 eV or more. Accordingly, the organic electroluminescent device of the present invention can improve all of the driving voltage, current efficiency, lifespan characteristics, etc. compared to the organic electroluminescent device using the _{conventional electron transport layer material (eg, Alq 3 ).}

Hereinafter, it will be described with reference to FIG. 1 as follows.

The organic electroluminescent device of the present invention sequentially includes an anode 100 , one or more organic material layers 300 , and a cathode 200 .

<Anode>

The organic electroluminescent device of the present invention includes an anode (100). The anode is formed on the substrate and injects holes into the organic material layer, for example, the hole injection layer 310 .

The material for forming the positive electrode is not particularly limited, and a conventional one known in the art may be used. For example, metals, such as vanadium, chromium, copper, zinc, and gold|metal; alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal such as ZnO:Al, SnO _{2 :Sb and an oxide;} conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, and polyaniline; and carbon black, but is not limited thereto.

A method of manufacturing the positive electrode is not particularly limited, and may be manufactured through a conventional method known in the art. For example, it may be formed by coating the anode material on the substrate through a known thin film forming method such as a sputtering method, an ion plating method, a vacuum deposition method, or a spin coating method.

The substrate is a plate-shaped member for supporting the organic electroluminescent device, and includes, for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet, but is not limited thereto.

<Cathode>

The organic electroluminescent device of the present invention includes a cathode (cathode). The cathode injects electrons into the organic material layer, for example, the electron injection layer.

The material for forming the negative electrode is not particularly limited, and a conventional one known in the art may be used. For example, metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead; alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

A method of manufacturing the negative electrode is not particularly limited, and like the positive electrode, it may be manufactured through a conventional method known in the art. For example, it may be formed by coating the cathode material on the organic material layer 300 (preferably, the electron injection layer 350) of one or more layers below through the above-described thin film forming method.

<One or more organic layers>

The organic electroluminescent device of the present invention includes one or more organic material layers 300 . The at least one organic material layer 300 includes a light emitting layer and an electron transport layer. Optionally, the present invention may further include one selected from the group consisting of a hole injection layer 310 , a hole transport layer 320 , and an electron injection layer 350 . However, in consideration of the characteristics of the organic electroluminescent device, it is preferable to include all of the above-described organic material layers.

According to one example, as shown in FIG. 1, the organic electroluminescent device of the present invention has a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340 on the anode 100, and The electron injection layer 350 may have a sequentially stacked structure.

Hereinafter, each organic material layer will be described.

(One) hole injection layer and hole transport layer

The hole injection layer 310 and the hole transport layer 320 serve to move the holes injected from the anode 100 to the light emitting layer 330 . The material constituting the hole injection layer 310 and the hole transport layer 320 is not particularly limited as long as it has a low hole injection barrier and high hole mobility, and if it is a hole injection layer / hole transport layer material commonly used in the art It can be used without limitation. Non-limiting examples of the material for the hole injection layer include metal porphyrine, oligothiophene, arylamine-based derivatives, hexanitrile hexaazatriphenylene-based derivatives, quinacridone-based derivatives, and perylene-based derivatives. based) derivatives, or conductive polymers such as anthraquinone derivatives, polyaniline derivatives, and polythiophene derivatives. Non-limiting examples of the material for the hole transport layer include an arylamine-based derivative, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion.

According to an example, the material of the hole injection layer 310 and the hole transport layer 320 may be a material having a hole mobility of about 1×10 ^-6 cm ² /V·s or more, respectively. At this time, if electrons and holes are not balanced due to the difference between the number of holes injected from the anode and the number of electrons injected from the cathode, electrons or holes that fail to form excitons due to recombination are accumulated in the light emitting layer, and these electrons or holes Oxidation and reduction may not occur smoothly in the light emitting layer, or may adversely affect the function of an adjacent layer, thereby reducing the lifespan of the organic electroluminescent device. Therefore, the electron transport layer of the present invention contains two or more organic compounds having excellent electron transport properties, preferably a first electron transporting organic compound and a second electron transporting organic compound having an ^{electron mobility of 1×10 -6} cm ^{2 /V·s or more.} include

(2) light emitting layer

The organic electroluminescent device of the present invention includes a light emitting layer 330 on the hole transport layer 320 .

The light emitting layer 330 is a layer in which holes and electrons meet to form excitons, and the color of light emitted by the organic electroluminescent device may vary depending on a material constituting the light emitting layer 330 .

The emission layer 330 may include a host and optionally further include a dopant. If the emission layer 330 uses a mixture of a host and a dopant, a mixing ratio of the host and the dopant is not particularly limited. For example, the content of the host may be in the range of about 70 to 99.9 wt%, and the content of the dopant may be in the range of about 0.1 to 30 wt%.

The host is not particularly limited as long as it is known in the art, and non-limiting examples thereof include alkali metal complexes; alkaline earth metal complexes; or a condensed aromatic ring derivative. Specifically, as the host material, an aluminum complex compound, beryllium complex compound, anthracene derivative, pyrene derivative, triphenylene derivative, carbazole derivative, dibenzofuran derivative, dibenzo It is preferred to use a thiophene derivative, or a combination of one or more thereof.

The dopant is not particularly limited as long as it is known in the art, and non-limiting examples thereof include an anthracene derivative, a pyrene derivative, an arylamine derivative, and a metal complex compound containing iridium (Ir) or platinum (Pt). have.

The above-described light emitting layer 330 may be a single layer or may be formed of a plurality of layers of two or more layers. When the light emitting layer 330 has a plurality of layers, the organic electroluminescent device may emit light of various colors. In addition, when the light emitting layer 330 is a plurality of layers, the driving voltage of the device increases, while the current value in the organic electroluminescent device becomes constant, so that it is possible to provide an organic electroluminescent device with improved luminous efficiency by the number of light emitting layers.

(3) electron transport layer

The organic electroluminescent device of the present invention includes an electron transport layer 340 stacked on the light emitting layer 330 . The electron transport layer 340 serves to move electrons injected from the cathode 200 or the electron injection layer 350 to the light emitting layer 330 .

The electron transport layer 340 may be formed of a material that facilitates electron injection and has high electron mobility. Accordingly, in the present invention, the electron transporting layer is formed by mixing the first electron transporting organic compound and the second electron transporting organic compound, which are different from each other (preferably have different electron mobility) but have excellent electron transport properties. However, in the present invention, as described above, at least one of the first electron transporting organic compound and the second electron transporting organic compound is a compound having a triplet energy of 2.0 eV or more. As a result, the present invention provides that electrons are easily injected from the cathode or electron injection layer, and the injected electrons are easily moved to the light emitting layer, and excitons formed in the light emitting layer are diffused into the electron transport layer while improving the lifespan of the organic electroluminescent device. can be prevented

)는 1.0 eV 이하일 수 있다. 이 경우, 엑시톤의 확산이 더 방지되어 유기 전계 발광 소자의 발광 효율이 더 향상될 수 있다. At this time, the difference between the triplet energy (T ₁ ) of the first electron-transporting organic compound and the triplet energy (T ₂ ) of the second electron-transporting organic compound (

) may be 1.0 eV or less. In this case, the diffusion of excitons is further prevented, so that the luminous efficiency of the organic electroluminescent device can be further improved.

In addition, the HOMO energy level (EH) of the first electron transporting organic compound and the second electron transporting organic compound is higher than that of the host in the light emitting layer. _{In particular, the difference between the HOMO energy level (EH ETL} ) of at least one of the first electron transporting organic compound and the second electron transporting organic compound and the HOMO energy level of the _host (EH host) (EH _ETL) - When the EH _host ) is in the range of 1.5 eV or less, since holes can be prevented from diffusing or moving to the electron transport layer, the recombination probability of electrons and holes in the light emitting layer can be increased to improve the luminous efficiency and lifespan of the organic light emitting device. have.

In addition, the first electron transporting organic compound and the second electron transporting organic compound are compounds excellent in electron transporting properties as described above. According to an example, the first electron-transporting organic compound and the second electron-transporting organic compound each have an electron mobility ^{as high as 1×10 -6} cm ² /V·s or more at room temperature (about 20 to 25° C.). When the electron transport layer is formed by mixing the first electron transport organic compound and the second electron transport organic compound having such electron mobility, electrons injected from the cathode can be smoothly injected into the light emitting layer. In this case, the first electron transporting organic compound and the second electron transporting organic compound may have different electron mobility. However, in the present invention, in order to balance the number of electrons injected from the cathode, it is appropriate for the hole transport layer ^{to include a material having a hole mobility of 1×10 -6} cm ² /V·s or more. As a result, electrons and holes reach the light emitting layer in a balanced manner and excitons can be efficiently formed, so that the lifespan of the organic electroluminescent device can be increased, and luminous efficiency and current efficiency can also be increased.

The content of the first electron-transporting organic compound and the second electron-transporting organic compound is not particularly limited. However, when the mixing ratio of the first electron transporting organic compound and the second electron transporting organic compound is 9:91 to 91:9 by weight, preferably 30:70 to 70:30 by weight, the optimum according to the mixing ratio It is possible to control the electron mobility, which can improve the lifespan of the material.

The first electron-transporting organic compound and the second electron-transporting organic compound usable in the present invention are different from each other, and each independently a moiety having a large electron withdrawing group (EWG) characteristic (hereinafter, 'EWG') moieties'). In this case, the first electron transporting organic compound and the second electron transporting organic compound are a moiety having a large electron donating group (EDG) characteristic together with the EWG moiety (hereinafter, 'EDG moiety') It may have a bipolar (bipolar) characteristic, including In this case, since the organic electroluminescent device of the present invention has high recombination of holes and electrons, not only electron transport property but also light emitting ability is improved, so that luminous efficiency, driving voltage, and lifespan characteristics can be improved overall.

Examples of the EWG moiety that can be used in the present invention include, but are not limited to, a moiety represented by Formula 1 to a moiety represented by Formula 4 below.

(In Formulas 1 to 4,

A plurality of Xs are the same as or different from each other, and each independently represents CR or N, provided that at least one of the plurality of Xs is N,

In this case, when CR is plural, a plurality of R are the same or different from each other, and each independently hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ aryl boronic of C _60, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or It may form a condensed ring with other adjacent R,

R of an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, phospho A pin group, a phosphine oxide group and an arylamine group are each independently 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, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ substituted by one or more substituent species selected from the group consisting of aryl amine group of the C ₆₀ or the beach hwandoem).

Specifically, non-limiting examples of the EWG moiety include a moiety of S1 to a moiety of S24, and preferably pyridine, pyrimidine, triazine, pyrazine, and the like.

In addition, the first electron-transporting organic compound and the second electron-transporting organic compound usable in the present invention are different from each other, and each independently may include one or more EDG moieties, preferably the EWG described above together with the EDG moiety. may contain moieties.

Examples of the EDG moiety usable in the present invention include condensed nitrogen heteroaromatic rings such as indole, carbazole, azepine, and the like; and condensed polycyclic aromatic rings such as biphenyl and triphenylene, but is not limited thereto.

As an example according to the present invention, the first electron-transporting organic compound and the second electron-transporting organic compound are different from each other, and each independently (i) a compound represented by the following formula (5); (ii) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (7); (iii) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (8); (iv) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (9); and (v) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (10), but is not limited thereto. Here, the compound of Formula 5 and the moiety of Formula 6 exhibit EDG properties.

(In Formula 5,

L _{1 To} L _{3 Are} the same as or different from each other, and each independently is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;

Ar _{6 To} Ar _{8 Are} the same as or different from each other, and each independently _{selected from the group consisting of hydrogen, deuterium, a C 6} ~ C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms, provided that Ar _{6 To} Ar ₈ Except when all are the same;

R _{4 To} R _{6 Are} the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ arylboronic group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ C ₆₀ is selected from the group consisting of an aryl amine;

a to c are each independently an integer of 0 to 3,

The L _{1 To} L ₃ Arylene group, heteroarylene group, Ar _{6 To} Ar ₈ Aryl group, heteroaryl group, R _{4 To} R ₆ Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group , a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, a phosphine group, a phosphine oxide group, and an arylamine group, each independently, deuterium, a halogen group, cya No group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms hetero Cycloalkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine of Oxide group and C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group).

Specifically, in Formula 5, L _{1 To} L _{3 Are} the same as or different from each other, and each independently is a single bond, or C ₆ ~ C ₆₀ Arylene group and 5 to 60 nuclear atoms consisting of a heteroarylene group It is selected from the group, preferably a single bond, or C ₆ ~ C ₁₈ It may be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. For example, L ₁ to L ₃ may each independently be a single bond, or may be selected from the group consisting of phenylene, biphenylene and carbazolylene.

In addition, Ar ₆ to Ar ₈ are the same as or different from each other, and each independently _{selected from the group consisting of hydrogen, deuterium, a C 6} to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms, at this time At least one of Ar ₆ to Ar ₈ is preferably selected from a heteroaryl group having 5 to 40 nuclear atoms including at least one element selected from the group consisting of N, O, and S. However, the case in which Ar ₆ to Ar ₈ are all the same is excluded.

(In Formula 6,

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 );}

X ₂ and X ₃ are the same as or different from each other, and each independently represent N or C(R ₂ ), wherein when C(R ₂ ) is plural, a plurality of R ₂ are the same as or different from each other;

Y ₁ to Y ₄ are the same as or different from each other, and each independently represents N or C(R ₁ ), wherein when R ₁ is plural, they are the same as or different from each other,

However, any _one of X 1 and X ₂ , X ₂ and X ₃ , Y ₁ and Y ₂ , Y ₂ and Y _{3 ,} and Y ₃ and Y ₄ is condensed with a moiety represented by any one of the following Chemical Formulas 7 to 10 (fused) to bind,

A plurality of R ₁ and R ₂ and Ar ₁ to Ar ₅ that are not condensed are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C ₁ to C ₄₀ of alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, Heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ arylamine group of C ₆₀ of selected from the group consisting of

The R _{1 To} R ₂ And Ar _{1 To} Ar ₅ An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group , alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and arylamine group are each independently, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ of alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, hetero of 5 to 40 nuclear atoms Aryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C than at ₆₀ the group consisting of an aryl amine of the selected one more substituents of substituted or unsubstituted).

(In Formulas 7 to 10,

X ₄ 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 ₅ to Y ₁₆ are the same as or different from each other, and each independently represents N or C(R ₃ ), wherein when C(R ₃ ) is a plurality, a plurality of R ₃ are the same as or different from each other,

However, Y ₅ and Y ₆ , Y ₆ and Y _{7 ,} Y ₇ and Y ₈ , Which of Y ₈ and Y ₉ , Y ₉ and Y _{10 ,} Y ₁₀ and Y ₁₁ , Y ₁₁ and Y ₁₂ , Y ₁₂ and Y _{13 ,} Y ₁₃ and Y ₁₄ , Y ₁₄ and Y ₁₅ , and Y ₁₅ and Y _{16 ?} One is condensed with a moiety of Formula 6,

A plurality of R ₃ , and Ar ₁ to Ar ₅ not condensed are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group , C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nuclear atom Number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, a C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ consisting of an aryl amine of the C ₆₀ of the selected from the group,

The R ₃ And Ar _{1 To} Ar ₅ Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron A group, an aryl boron group, a phosphine group, a phosphine oxide group, and an arylamine group are each independently a 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 , C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ arylboronic a C ₆₀ group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ substituted by one or more selected from the group consisting of an aryl amine of the C ₆₀ or unsubstituted).

In the present invention, the moiety represented by Formula 6 may be embodied as a moiety represented by any one of the following A-1 to A-24, but is not limited thereto. At this time, in consideration of the physical and chemical properties of the compound, it is preferable when the moiety of Formula 6 is one of the moieties represented by the following A-1 to A-6.

(In A-1 to A-24 above,

R ₂ , Y ₁ to Y ₄ and Ar ₁ to Ar ₅ are each as defined in Formula 6 above)

In the present invention, the compound (ii) formed by condensation of the moiety of Chemical Formula 6 and the moiety of Chemical Formula 7 may be any one of compounds represented by the following Chemical Formulas a to f, but is not limited thereto.

[Formula a]

[Formula b]

[Formula c]

[Formula d]

[Formula e]

[Formula f]

(In the formulas a to f,

X ₁ to X ₄ and Y ₁ to Y ₈ are as defined in Chemical Formulas 6 and 7, respectively).

Compound (ii) formed by condensation of a moiety of Formula 6 and a moiety of Formula 7 may be embodied as any one of Formulas B-1 to B-30, but is not limited thereto. Since the following compounds contain at least one indole, they have strong electron donor (EDG) properties.

(In the formulas B-1 to B-30,

Ar ₁ and R ₁ to R ₃ are as defined in Formulas 6 and 7, respectively,

Specifically, Ar ₁ is selected from the group consisting of a C ₆ ~ C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms,

R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms,

An aryl group, a heteroaryl group, and R ₁ to the alkyl group of R ₃ of the above Ar _1, an aryl group, a heteroaryl group, each independently, a deuterium, a halogen group, a cyano group, an alkyl group of a nitro group, an amino group, C ₁ ~ C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, number of nuclear atoms 5 to 40 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 1} ~ C 40 of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ from the group consisting of an aryl amine of the C ₆₀ of the unsubstituted or substituted with one or more selected types).

In the present invention, the compound (iii) formed by condensation of the moiety of Chemical Formula 6 and the moiety of Chemical Formula 8 may be any one of compounds represented by the following Chemical Formulas g to n, and the moiety of Chemical Formula 6 and Chemical Formula 9 Compound (iv) formed by condensation of a moiety may be a compound represented by the following formula o or p, and the compound (v) formed by condensation of a moiety of formula 6 and a moiety of formula 10 is represented by the following formula q It may be a compound to be used, but is not limited thereto. Since the compounds of the following formulas g to q contain one or more azepine moieties, they have strong electron donor properties (EDG).

[Formula g]

[Formula h]

[Formula i]

[Formula j]

[Formula k]

[Formula l]

[Formula m]

[Formula n]

[Formula o]

[Formula p]

[Formula q]

(In the above formulas g to q,

X ₁ , X ₃ to X _4, Y ₁ to Y ₁₆ are each as defined in Formulas 6 to 10,

Specifically, X ₁ and X ₄ are the same as or different from each other, and each independently _{is preferably O, S or N(Ar 1} ), and more preferably all of N(Ar ₁ ), in which case N(Ar _{1 ).} ) is plural, plural Ar _1s are the same or different;

Y _{1 To} Y _{4 Are} the same as or different from each other, and each independently represents N or C(R ₁ ), of which Y _{1 To} Y ₄ are preferably all C(R ₁ ), in which case C(R ₁ ) is in the case of plural, plural R _1s are the same or different;

X ₃ is N or C(R ₂ );

Y ₅ to Y ₁₆ are the same as or different from each other, and each independently represents N or C(R ₃ ), of which Y ₅ to Y ₁₄ are preferably all C(R ₃ ), in which case C(R ₃ ) is In case of plural, plural R ₃ is the same or different;

Ar ₁ is selected from the group consisting of a C ₆ ~ C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms,

R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms,

An aryl group, a heteroaryl group, and R ₁ to the alkyl group of R ₃ of the above Ar _1, an aryl group, a heteroaryl group, each independently, a deuterium, a halogen group, a cyano group, an alkyl group of a nitro group, an amino group, C ₁ ~ C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, number of nuclear atoms 5 to 40 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 1} ~ C 40 of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ from the group consisting of an aryl amine of the C ₆₀ of the unsubstituted or substituted with one or more selected types).

According to an example of the present invention, in Formulas a to p, X ₁ and X ₄ are each independently N(Ar ₁ ) or S. It is preferable. That is, X ₁ is N(Ar ₁ ) and X ₄ is S; or X ₁ is S and X ₄ is N (Ar ₁ ); Alternatively, it is preferable that _{both X 1} and X ₄ are N(Ar _{1 ).}

In addition, Ar ₁ is selected from the group consisting of a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, and the aryl group and heteroaryl group of Ar ₁ are each independently, C ₁ ~ C ₄₀ It is preferably unsubstituted or substituted with one or more selected from the group consisting of an alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and an arylamine group of C ₆ to C _{60 .}

Also, Ar ₂ to Ar ₅ are the same as or different from each other, and each independently selected from _{the group consisting of a C 1} to C ₄₀ alkyl group (eg, a methyl group), and a C ₆ to C ₆₀ aryl group (eg, a phenyl group), Ar ₂ To Ar ₅ Aryl group, heteroaryl group is each independently, C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, and C ₆ ~ C ₆₀ Arylamine It is preferably unsubstituted or substituted with one or more selected from the group consisting of a group.

Specifically, the first electron-transporting organic compound and the second electron-transporting organic compound are different from each other, and each independently be any one of the compounds of (i) to (v), but at least one EWG in the compound A moiety may be introduced. In this case, the EWG moiety may be any one of Chemical Formulas 1 to 4. In this case, since the compound is a bipolar compound, the recombination of holes and electrons is high, and thus, the luminous efficiency, driving voltage, and lifespan characteristics of the organic electroluminescent device are improved as well as the electron transport property as well as the light emitting ability. can

More specifically, the first electron transporting organic compound and the second electron transporting organic compound are different from each other, and each may be independently selected from the group consisting of the following compounds LE-01 to LE-36, but is not limited thereto.

Alkyl in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like. can be heard

Alkenyl in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds, and examples thereof include vinyl, allyl ), isopropenyl, 2-butenyl, and the like.

Alkynyl in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds, and examples thereof include ethynyl, 2- propanyl (2-propynyl) and the like.

Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, and the like.

Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. In addition, two or more rings may be simply attached to each other (pendant) or may include a condensed form, and may include a condensed form with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, and diphenyloxy.

Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R' means 1 to 40 alkyl, and includes a linear, branched or cyclic structure. interpreted as Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or It is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like.

Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.

The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

A method of manufacturing the above-described electron transport layer 340 is not particularly limited as long as it is a method known in the art, and for example, a co-evaporation method, a vacuum deposition method, a solution coating method, and the like.

For example, the first and second electron-transporting compounds are respectively placed in the first and second heat sources, and the materials are simultaneously heated to co-deposit to form the electron-transporting layer 340 . At this time, it is preferable to perform co-deposition at an appropriate ratio by controlling the evaporation rates per second of the first heat source and the second heat source at a vacuum degree of ^{1×10 -0.6 torr or less.} In addition, the usage-amount of each electron-transporting compound located in a 1st heat source and a 2nd heat source is not specifically limited.

In another example, the first and second electron transport compounds are mixed in an appropriate ratio, and then the mixture is placed in one heat source and then heated to co-deposit to form the electron transport layer 340 . At this time, it is preferable to carry out at a vacuum degree of ^{1×10 -0.6 torr or less.} In addition, the usage-amount of the said 1st and 2nd electron-transporting compound is not specifically limited.

(4) electron injection layer

The organic electroluminescent device of the present invention includes an electron injection layer 350 stacked on the electron transport layer 340 . The electron injection layer 350 serves to move electrons injected from the cathode 200 to the electron transport layer 340 .

The material constituting the electron injection layer 350 is not particularly limited as long as it is a material with easy electron injection and high electron mobility, and for example, alkali metals, alkaline earth metals and their halides, oxides, peroxides, sulfides, etc. , specifically alkali metals such as Ce and Li, alkaline earth metals such as Ca, Sr, Ba, Ra, lithium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, fluorides such as barium fluoride, lithium oxide, etc. oxides, and the like, but are not limited thereto. For example, LiF may be used as the electron injection layer 350 .

Optionally, the present invention may further include an organic layer (not shown) for blocking the movement of electrons and excitons between the hole transport layer 320 and the light emitting layer 330 in addition to the above-described organic material layer.

This organic layer has a high LUMO value to prevent electrons from moving to the hole transport layer 320 , and has a high triplet energy to prevent excitons of the light emitting layer 330 from diffusing into the hole transport layer 302 . The material constituting the organic layer is not particularly limited, and non-limiting examples thereof include carbazole derivatives and arylamine derivatives.

A method of manufacturing the above-described organic material layer 300 is not particularly limited, and for example, a vacuum deposition method, a solution coating method, and the like. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, thermal transfer, and the like.

The organic electroluminescent device according to the present invention has a structure in which the anode 100, the organic material layer 300 and the cathode 200 are sequentially stacked. In some cases, an insulating layer (not shown) or an adhesive layer (not shown) may be further included between the anode 100 and the organic material layer 300 or between the cathode 200 and the organic material layer 300 . The organic electroluminescent device of the present invention can have excellent lifespan characteristics because the half-life time of initial brightness is increased while maintaining maximum luminous efficiency when voltage and current are applied.

Hereinafter, the present invention will be described in detail through examples, but the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[ preparation example 1-36] - Preparation of compounds LE-01 to LE-36

The following compounds LE-01 to LE-36 were prepared as electron transport layer materials in Examples 1 to 13, and their triplet energy, HOMO energy level, and electron mobility were measured by a method known in the art, respectively. Table 1 shows. Here, the electron mobility is measured by forming a film of the bipolar compound to a thickness of 1 ㎛ (Transition time) of the carrier.

compound Calculated value (B3LYP/6-31G*) measured value Triplet energy (eV) HOMO energy level (eV) Electron mobility (cm ² /V s) LE-01 2.39 5.54 8.9×10 ^-5 LE-02 2.45 5.50 5.8×10 ^-6 LE-03 2.54 5.71 8.8×10 ^-5 LE-04 2.53 5.60 7.6×10 ^-5 LE-05 2.65 5.58 7.5×10 ^-6 LE-06 2.50 5.64 9.6×10 ^-6 LE-07 2.48 5.65 9.2×10 ^-5 LE-08 2.74 6.01 5.1×10 ^-5 LE-09 2.38 5.71 9.9×10 ^-5 LE-10 2.35 5.69 1.0×10 ^-5 LE-11 2.81 6.01 1.3×10 ^-4 LE-12 2.78 6.05 1.0×10 ^-4 LE-13 2.59 5.82 1.1×10 ^-4 LE-14 2.51 5.51 2.1×10 ^-5 LE-15 2.59 5.56 7.5×10 ^-5 LE-16 2.54 5.51 8.5×10 ^-6 LE-17 2.43 5.64 7.8×10 ^-6 LE-18 2.50 5.68 6.5×10 ^-4 LE-19 2.45 5.73 7.5×10 ^-6 LE-20 2.56 5.70 5.8×10 ^-5 LE-21 2.48 5.60 6.4×10 ^-5 LE-22 2.57 5.70 7.0×10 ^-5 LE-23 2.53 5.60 7.0×10 ^-4 LE-24 2.47 5.70 6.6×10 ^-6 LE-25 2.43 5.83 8.1×10 ^-6 LE-26 2.39 5.69 9.5×10 ^-6 LE-27 2.41 5.99 3.7×10 ^-5 LE-28 2.35 5.82 5.1×10 ^-5 LE-29 2.37 5.75 3.9×10 ^-5 LE-30 2.45 6.01 5.6×10 ^-6 LE-31 2.40 6.19 6.4×10 ^-6 LE-32 2.34 6.09 7.0×10 ^-5 LE-33 2.55 5.70 7.5×10 ^-4 LE-34 2.47 5.68 6.6×10 ^-5 LE-35 2.43 6.21 8.1×10 ^-5 LE-36 2.39 6.15 9.5×10 ^-6

[ Example 1 to 13] - organic electric field Manufacturing of light emitting devices

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was ultrasonically cleaned with distilled water. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.

On the ITO transparent substrate (electrode) prepared as above, DS-205 (Doosan) (80 nm) / NPB (15 nm) / 95% by weight of ADN + 5% by weight of DS-405 (Doosan) (30 nm ) / Compounds of Table 2 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in the order to prepare an organic electroluminescent device. At this time, the NPB and ADN used are as follows.

[ comparative example 1] - organic electric field Manufacturing of light emitting devices

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that _{Alq 3} was used instead of the compounds (LE-01 + LE-18) used as the electron transport layer material in Example 1. At this time, Alq ₃ used is as follows.

[ comparative example 2 to 4] - organic electric field Manufacturing of light emitting devices

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that LE-05, LE-22, and LE-36 were used as the electron transport layer material in Example 1, respectively.

[ Experimental example One]

For the organic electroluminescent devices prepared in Examples 1 to 13 and Comparative Example 1, respectively, the driving voltage, current efficiency, and lifetime (T ₉₇ ) were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 2 below shown in Here, the lifetime (T ₉₇ ) was measured by measuring the time at which the emission luminance became 97% through a life measuring instrument.

Electron transport layer material (mixing ratio) Driving voltage (V) Current Efficiency (cd/A) Lifetime (hr) Example 1 LE-01 + LE-18 (50:50) 4.2 6.5 61 Example 2 LE-03 + LE-19 (50:50) 4.4 6.3 52 Example 3 LE-05 + LE-21 (50:50) 4.3 6.4 77 Example 4 LE-08 + LE-23 (50:50) 4.7 6.2 68 Example 5 LE-09 + LE-26 (50:50) 4.5 6.6 59 Example 6 LE-11 + LE-28 (50:50) 4.4 6.4 62 Example 7 LE-13 + LE-29 (50:50) 4.6 6.5 82 Example 8 LE-14 + LE-32 (50:50) 4.6 6.3 74 Example 9 LE-15 + LE-34 (50:50) 4.1 6.2 78 Example 10 LE-02 + LE-06 (30:70) 4.9 6.6 66 Example 11 LE-10 + LE-12 (40:60) 4.8 6.1 69 Example 12 LE-17 + LE-20 (60:40) 4.4 6.1 55 Example 13 LE-22 + LE-36 (70:30) 4.6 6.5 59 Comparative Example 1 Alq ₃ 5.2 5.6 30 Comparative Example 2 LE-05 5.0 5.8 40 Comparative Example 3 LE-22 5.1 5.9 45 Comparative Example 4 LE-36 5.1 5.8 38

Referring to Table 2, it was confirmed that the organic electroluminescent devices of Examples 1 to 13 had a lower driving voltage, higher current efficiency, and excellent lifespan than the organic electroluminescent devices of Comparative Examples 1 to 4.

100: positive electrode, 200: negative electrode,
300: organic layer, 310: hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer

Claims (13)

anode;
cathode; and
One or more organic material layers interposed between the anode and the cathode and containing an electron transport layer
including,
The electron transport layer includes a first electron transporting organic compound and a second electron transporting organic compound different from each other,
The first electron transporting organic compound and the second electron transporting organic compound each have an electron mobility of 1Х10 ^-6 cm ² /V·s or more at room temperature,
The first electron-transporting organic compound and the second electron-transporting organic compound are characterized in that they are mixed in a weight ratio of 9:91 to 91:9, an organic electroluminescent device. According to claim 1,
At least one of the first electron transporting organic compound and the second electron transporting organic compound is characterized in that it comprises an aromatic ring, a heterocyclic ring, a nitrogen-containing heteroaromatic ring or a polycyclic aromatic ring, an organic electroluminescent device. According to claim 1,
The difference between the triplet energy (T ₁ ) of the first electron transporting organic compound and the triplet energy (T ₂ ) of the second electron transporting organic compound (

) is an organic electroluminescent device, characterized in that 1.0 eV or less. According to claim 1,
The organic layer further contains a light emitting layer,
The light emitting layer includes a host,
_{The difference between the HOMO energy level (EH ETL} ) of at least one of the first electron transporting organic compound and the second electron transporting organic compound and the HOMO energy level of the _host (EH host ) (EH _ETL - EH _host ) is 1.5 eV or less characterized in that, an organic electroluminescent device. According to claim 1,
At least one of the first electron transporting organic compound and the second electron transporting organic compound has a triplet energy of 2.0 eV or more, an organic electroluminescent device. According to claim 1,
At least one of the first electron transporting organic compound and the second electron transporting organic compound is a compound containing one or more N, an organic electroluminescent device. 7. The method of claim 6,
The first electron transporting organic compound and the second electron transporting organic compound are different from each other, and each independently include at least one moiety selected from the group consisting of a moiety represented by the following Chemical Formula 1 to a moiety represented by Chemical Formula 4 Which, the organic electroluminescent device:
[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

(In Formulas 1 to 4,
A plurality of Xs are the same as or different from each other, and each independently represents CR or N, provided that at least one of the plurality of Xs is N,
In this case, when CR is plural, a plurality of R are the same or different from each other, and each independently hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ aryl boronic of C _60, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or It may form a condensed ring with other adjacent R,
An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, phospho A pin group, a phosphine oxide group and an arylamine group are each independently 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, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, substituted with one or more substituent species selected from the group consisting of an arylamine group of C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₆₀ of hwandoem or unsubstituted). 8. The method of claim 7,
When two or more of a plurality of Xs are CR, a plurality of Rs are the same as or different from each other, and each independently hydrogen, deuterium (D), a cyano group, a C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms a heteroaryl group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide of the group and a C ₆ ~ selected from the group consisting of an aryl amine of the C _60, or to form a different R and condensed ring or adjacent can,
The aryl group, heteroaryl group, phosphine group, phosphine oxide group and arylamine group of R are each independently, heavy water, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alke Nyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ phosphine group, C ₁ ~ C ₄₀ A phosphine oxide group and a C ₆ ~ C ₆₀ An organic electroluminescent device that is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group. 8. The method of claim 7,
When two or more of the plurality of Xs are CR, and one of the plurality of Rs is a C ₆ ~ C ₆₀ aryl group, the aryl groups are each independently deuterium (D), a cyano group, a C ₆ ~ C ₆₀ aryl group, An organic electroluminescent device that is unsubstituted or substituted with at least one substituent selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, and a C ₁ to C _{40 phosphine group.} According to claim 1,
The first electron-transporting organic compound and the second electron-transporting property are each independently comprising at least one moiety selected from the group consisting of a moiety of S1 to a moiety of S24, an organic electroluminescent device:

. According to claim 1,
The first electron transporting organic compound and the second electron transporting organic compound are different from each other, and each independently (i) a compound represented by the following Chemical Formula 5; (ii) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (7); (iii) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (8); (iv) a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (9); And (v)) an organic electroluminescent device selected from the group consisting of a compound formed by condensation of a moiety represented by the following formula (6) and a moiety represented by the following formula (10):
[Formula 5]

(In Formula 5,
L _{1 To} L _{3 Are} the same as or different from each other, and each independently is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;
Ar _{6 To} Ar _{8 Are} the same as or different from each other, and each independently _{selected from the group consisting of hydrogen, deuterium, a C 6} ~ C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms, provided that Ar _{6 To} Ar ₈ except when all are the same;
R _{4 To} R _{6 Are} the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ arylboronic group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ C ₆₀ is selected from the group consisting of an aryl amine;
a to c are each independently an integer of 0 to 3,
The L _{1 To} L ₃ Arylene group, heteroarylene group, Ar _{6 To} Ar ₈ Aryl group, heteroaryl group, R _{4 To} R ₆ Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group , a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, a phosphine group, a phosphine oxide group, and an arylamine group are each independently, deuterium, a halogen group, cya No group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C40 cycloalkyl group, heterocyclo having 3 to 40 nuclear atoms Alkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group and C ₆ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group);
[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

(In Formulas 6 to 10,
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 ),}
X ₂ and X ₃ are the same as or different from each other, and each independently represent N or C(R ₂ ), wherein when C(R ₂ ) is plural, a plurality of R ₂ are the same as or different from each other,
Y ₁ to Y ₄ are the same as or different from each other, and each independently represents N or C(R ₁ ), wherein when C(R ₁ ) is a plurality, a plurality of R ₁ are the same as or different from each other,
However, any _one of X 1 and X ₂ , X ₂ and X ₃ , Y ₁ and Y ₂ , Y ₂ and Y ₃ , and Y ₃ and Y ₄ is condensed with a moiety represented by any one of Formulas 7 to 10 bind;
X ₄ is selected from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar _{5 ), and Y 5} to Y ₁₆ are the same or or different, each independently N or C(R ₃ ), wherein when C(R ₃ ) is plural, a plurality of R ₃ are the same as or different from each other,
However, Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , Y ₈ and Y ₉ , Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ , Y ₁₁ and Y ₁₂ , Y ₁₂ and Y ₁₃ , Any one of Y ₁₃ and Y ₁₄ , Y ₁₄ and Y ₁₅ , and Y ₁₅ and Y ₁₆ is condensed with a moiety of Formula 6,
A plurality of R ₁ to R ₃ and Ar ₁ to Ar ₅ that are not condensed are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C ₁ to C ₄₀ of alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, Heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ arylamine group of C ₆₀ of selected from the group consisting of
The R _{1 To} R ₃ And Ar _{1 To} Ar ₅ An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group , alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and arylamine group are each independently, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ of alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryl group, hetero of 5 to 40 nuclear atoms Aryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C than at ₆₀ the group consisting of an aryl amine of the selected one more substituents of substituted or unsubstituted). 12. The method of claim 11,
The compound of (ii) is selected from the group consisting of compounds represented by the following formulas a to f,
The compound of (iii) is selected from the group consisting of compounds represented by the following formulas g to n,
The compound of (iv) is selected from the group consisting of compounds represented by the following formula o or p,
The compound of (v) is selected from the group consisting of compounds represented by the following formula q, an organic electroluminescent device:
[Formula a]

[Formula b]

[Formula c]

[Formula d]

[Formula e]

[Formula f]

[Formula g]

[Formula h]

[Formula i]

[Formula j]

[Formula k]

[Formula l]

[Formula m]

[Formula n]

[Formula o]

[Formula p]

[Formula q]

(In the formulas a to q,
X ₁ to X ₄ and Y ₁ to Y ₁₆ are each as defined in claim 11). According to claim 1,
The first electron-transporting organic compound and the second electron-transporting organic compound are different from each other, and each independently selected from the group consisting of the following compounds LE-01 to LE-36, an organic electroluminescent device:

.

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