KR20230097365A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic compound having excellent heat resistance, carrier transport ability, luminous ability, etc., and luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers. It relates to an organic electroluminescent device with improved properties such as

Description

Organic compound and organic electroluminescent device using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a novel compound having excellent heat resistance, carrier transport ability, and light emitting ability, and by including the same in one or more organic material layers, luminous efficiency, driving voltage, lifespan, etc. It relates to an organic electroluminescent device with improved characteristics.

When a voltage is applied between the two electrodes of the organic electroluminescent device (hereinafter referred to as 'organic EL device'), holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified according to its function into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like.

Materials for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emitting color. In addition, yellow and orange light emitting materials are also used as light emitting materials for implementing better natural colors. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Until now, NPB, BCP, Alq ₃ and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant/host materials for light emitting materials. In particular, as a phosphorescent material that has a great advantage in terms of efficiency improvement among light emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ are used as blue, green, and red dopants. used as a material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional organic layer materials are advantageous in terms of light emitting properties, but have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifespan in organic EL devices. Therefore, there is a demand for the development of organic layer materials with excellent performance.

An object of the present invention is an organic layer material of an organic electroluminescent device, specifically a light emitting layer material, a lifespan improvement layer material, a light emitting auxiliary layer material, an electron transport auxiliary layer material and / or an electron transport auxiliary layer material and / or electron It is to provide a novel compound that can be used as a material for a transport layer or the like.

Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound described above.

In order to achieve the above object, the present invention provides a compound represented by Formula 1 below:

X is O or S;

m1 and m2 are each 0 or 1, provided that m1+m2=1,

A is a substituent represented by Formula 2 below,

n is 2 or 3;

Z ₁ to Z ₃ are the same as or different from each other, and are each independently N or C(R ₃ ), provided that at least one of Z ₁ to Z ₃ is N, where C(R ₃ ) is plural, plural R ₃ of are the same as or different from each other,

R ₁ to R ₃ are the same as or different from each other, and are each independently hydrogen, deuterium, tritium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~C ₄₀ alkyl group, 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 ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ selected from the group consisting of arylamine group, or condensation by combining with adjacent groups form a ring,

a is an integer from 1 to 8;

A plurality of Ar ₁ are the same as or different from each other,

Ar ₁ is C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, 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 ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group And C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,

An alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, and an alkylboron of R ₁ to R ₃ and Ar ₁ Group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group , C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 ~ C ₆₀ Arylboron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ Arylphosphine oxide group, C ₆ ~ C ₆₀ Substituted with one or more substituents selected from the group consisting of arylamine group or unsubstituted, and when the substituents are plural, they are the same as or different from each other).

In addition, the present invention is an anode; cathode; It includes one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the above-mentioned compound.

The compound of the present invention can be used as a material for an organic material layer of an organic electroluminescent device because it has excellent electron injection and transport ability, light emitting ability, thermal stability, and electrochemical stability. In particular, when the compound of the present invention is used as at least one of a host material, an electron transport layer material, and an electron transport auxiliary layer material, an organic electroluminescent device having low driving voltage, high efficiency, and long lifespan characteristics can be manufactured compared to conventional materials, Furthermore, a full color display panel with improved performance and lifespan can be manufactured.

Effects according to the present invention are not limited by the contents exemplified above, and more diverse effects are included in the present specification.

1 is a schematic cross-sectional view of an organic electroluminescent device according to a first embodiment of the present invention.
2 is a schematic cross-sectional view of an organic electroluminescent device according to a second embodiment of the present invention.
3 is a schematic cross-sectional view of an organic electroluminescent device according to a third embodiment of the present invention.

Hereinafter, the present invention will be described.

<New compound>

Compounds according to the present invention may contain spiro[fluorene-xanthene] moieties or spiro[fluorene-thioxathene] moieties; an azine-based substituent bonded to any one benzene site in the moiety through a linker group (eg, a biphenylene group, a terphenylene group, etc.); and a basic structure including various substituents (eg, phenyl group, biphenyl group, naphthyl group, etc.) introduced at any one benzene moiety in the moiety, and is represented by Formula 1 above. The compound represented by Chemical Formula 1 according to the present invention is excellent in electron injection and transport ability, electrochemical stability, heat resistance, etc., and thus an electron transport layer material or an electron transport auxiliary layer capable of improving high efficiency, long lifespan, and driving voltage characteristics of an organic electroluminescent device. material can be used.

Specifically, in the compound represented by Formula 1, the spiro [fluorene-xanthene] moiety or the spiro [fluorene-thioxanthene] moiety has a high electron withdrawing group (electron withdrawing group, EWG) When the phosphorus azine-based substituent is bonded through a biphenylene group or a terphenylene group as a linker, structural stability and electrochemical stability are excellent, as well as electron injection and transport ability are excellent due to increased electron mobility. In addition, by introducing an electron donating group (EDG) having weak electron donating ability such as a phenyl group to the spiro [fluorene-xanthene] moiety or the spiro [fluorene-thioxanthene] moiety, electron Through the effect of increasing the electron density, the electron donating of the spiro[fluorene-xanthene] moiety or the spiro[fluorene-thioxanthene] moiety is improved, thereby improving the stability of the molecule. can Therefore, when the compound represented by Chemical Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light emitting layer, and as a result, the The driving voltage is lowered, and high efficiency and long lifespan characteristics can be implemented.

As described above, the compound represented by Formula 1 according to the present invention has excellent electron injection and transport capabilities, thermal stability, and electrochemical stability. Therefore, the compound of the present invention is used as an organic material layer of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), an electron transport layer/injection layer material, an electron transport auxiliary layer material, and a lifespan improvement layer material. It can be used, more preferably as an electron transport layer material or an electron transport auxiliary layer material. Performance and lifetime characteristics of the organic electroluminescent device including the compound of the present invention can be greatly improved, and the performance of a full-color organic light emitting panel to which the organic electroluminescent device is applied can also be maximized.

In the compound represented by Formula 1 according to the present invention, X is O or S. The compound of Formula 1 has excellent electron transport ability compared to the case where X is N or C. Therefore, when the compound of Formula 1 according to the present invention is used as an electron transport layer material, efficiency and driving voltage improvement effect can be improved by improving electron transport capability.

Also, in the compound represented by Formula 1, m1 and m2 are each 0 or 1, provided that m1+m2=1.

Depending on m1 and m2, the compound represented by Formula 1 may be a compound represented by any one of Formulas 3 to 6, but is not limited thereto.

In Formulas 3 to 6,

X, n, R ₁ , R ₂ , Ar ₁ and Z ₁ to Z ₃ are each as defined in Formula 1 above;

a1 is an integer from 0 to 4;

a2 is an integer from 0 to 3;

In the compound represented by Chemical Formula 1, A is a C ₁₂ to C ₁₈ aryl group substituted with an azine-based substituent, and is a substituent represented by Chemical Formula 2.

모이어티는 하기 링커기 L-1 내지 L-12로 이루어진 군에서 선택된 것일 수 있는데, 이에 한정되지 않는다.In Formula 2, n is an integer of 2 or 3. Depending on this n, in the substituent of Formula 2, the

The moiety may be selected from the group consisting of the following linker groups L-1 to L-12, but is not limited thereto.

In the linker groups L-1 to L-12,

* indicates a site connected to the spiro[fluorene-xanthene (or thioxanthene)] moiety of Formula 1 and the azine-based substituent of Formula 2, respectively.

Hydrogen of these linker groups L-1 to L-12 is deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₁₂ alkyl group, C ₆ ~ C ₁₀ aryl group, and 5 to 10 nuclear atoms It may be substituted or unsubstituted with one or more substituents selected from the group consisting of two heteroaryl groups.

Also, in Formula 2, Z ₁ to Z ₃ are the same as or different from each other, and each independently represent N or C(R ₃ ), provided that at least one of Z ₁ to Z ₃ is N. In this case, when the number of C(R ₃ ) is plural, the plurality of R ₃ s are the same as or different from each other. According to an example, two of the Z ₁ to Z ₃ may be N, and the rest may be C(R ₃ ). According to another example, all of Z ₁ to Z ₃ may be N. In this way, by including a heteroaromatic ring containing at least one nitrogen, the compound of the present invention exhibits better electron absorption characteristics and is advantageous for electron injection and transport.

Wherein R ₃ is hydrogen, deuterium, tritium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or an adjacent group (eg, R ₃ -R ₁ , R ₃ -R ₂ , R ₃ -R ₃ ) to form a condensed ring, specifically deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ It may be selected from the group consisting of an alkynyl group, a C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And, more specifically, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, It may be selected from the group consisting of a heterocycloalkyl group having 3 to 20 nuclear atoms, a C ₆ ~C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

An alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl 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 of R ₃ , Arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, and specifically independently deuterium, halogen, cyano group, nitro 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, nucleus It may be unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocycloalkyl group having 3 to 40 atoms, a C ₆ ~C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same as or different from each other.

모이어티는 하기 치환기 Az1 내지 Az3 중 어느 하나일 수 있다.According to these Z ₁ to Z ₃ , in the substituent of Formula 2, the

The moiety may be any one of the following substituents Az1 to Az3.

In the substituents Az1 to Az3,

모이어티와 연결되는 부분이고,* is the formula (2)

It is a part connected to the moiety,

Wherein R ₁ and R ₂ are the same as or different from each other, and are each independently hydrogen, deuterium, tritium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 ~ A C ₆₀ arylboron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or an adjacent group (eg : R ₁ -R ₃ , R ₂ -R ₃ , R ₁ -R ₂ ) to form a condensed ring, specifically deuterium, halogen, cyano group, nitro 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 heterocycloalkyl group, C ₆ ~C ₆₀ aryl group, and 5 nuclear atoms to 60 heteroaryl groups, more specifically, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ It may be selected from the group consisting of an alkynyl group, a C ₃ ~ C ₂₀ cycloalkyl group, a heterocycloalkyl group having 3 to 20 nuclear atoms, a C ₆ ~ C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. .

An alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, and an aryl of R ₁ and R ₂ The boron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~C ₄₀ alkyl group, 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 ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups and, specifically, each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cyclo It may be unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same as or different from each other.

According to an example, R ₁ and R ₂ are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen, deuterium, tritium, and C ₆ ~ C ₆₀ aryl groups, wherein R ₁ and R ₂ The aryl group of deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms , C ₁ ~ C ₄₀ alkyl group, 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 ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C It is substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, and when the substituents are plural, they are the same as or different from each other.

Also, in Formula 1, a is an integer of 1 to 8, and a plurality of Ar ₁ are the same as or different from each other.

In addition, Ar ₁ is a C ₂ ~ C ₄₀ alkenyl group, a C ₂ ~ C ₄₀ alkynyl group, a C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, or a C ₁ ~ C ₄₀ alkyl group. , C ₆ ~ C ₆₀ aryl group, heteroaryl group having 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 aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine It is selected from the group consisting of oxide group and C ₆ ~ C ₆₀ arylamine group, specifically deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ Selected from the group consisting of a C ₄₀ alkynyl group, a C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms It may be, more specifically, heavy hydrogen, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cyclo It may be selected from the group consisting of an alkyl group, a heterocycloalkyl group having 3 to 20 nuclear atoms, a C ₆ ~C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

An _alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl 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, Arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, and specifically independently deuterium, halogen, cyano group, nitro 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, nucleus It may be unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocycloalkyl group having 3 to 40 atoms, a C ₆ ~C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same as or different from each other.

According to one example, a is 1, Ar ₁ may be a C ₆ ~ C ₆₀ aryl group, and the Ar ₁ aryl group is deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~C ₄₀ alkyl group, C ₆ ~C ₆₀ aryl group, 5 to 60 nuclear atoms Two heteroaryl groups, 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 An alkyl boron group of C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group It may be substituted or unsubstituted with one or more substituents, and when the substituents are plural, they are the same as or different from each other.

Depending on the bonding position of A and Ar ₁ described above, the compound represented by Formula 1 may be a compound represented by any one of Formulas 7 to 22, but is not limited thereto.

In Formulas 7 to 22,

X, n, R ₁ , R ₂ , Ar ₁ and Z ₁ to Z ₃ are each as defined in Formula 1 above.

The compound represented by Formula 1 according to the present invention described above may be further embodied in the following compounds 1 to 180, but is not limited thereto.

In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or a heteroatom such as Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. 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, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. can include Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl. Also, "arylsilyl" means a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono- as well as di- and tri-arylsilyl.

In the present invention, "alkyl boron group" refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms, and "aryl boron group" refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.

In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In the present invention, "arylphosphinyl group" means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamines.

In the present invention, "heteroarylamine" means an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.

In the present invention, (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 nuclear atoms.

In the present invention, "condensed ring" is a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclear atoms, a condensed heteroaromatic ring having 5 to 60 nuclear atoms, It means a spiro ring having 3 to 60 carbon atoms or a combination thereof.

<Organic electroluminescent device>

Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as 'organic EL device') including the compound represented by Formula 1 described above.

Specifically, as shown in FIGS. 1 to 3, the organic electroluminescent device according to the present invention includes an anode 100, a cathode 200, and interposed between the anode and the cathode. It includes one or more organic material layers 300, and at least one of the one or more organic material layers includes the compound represented by Chemical Formula 1. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers 300 may include at least one of a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and an electron injection layer 350, Optionally, an electron transport auxiliary layer 360 may be additionally included. At this time, at least one organic material layer 300 includes the compound represented by Chemical Formula 1 above. Specifically, the organic material layer including the compound of Chemical Formula 1 may be at least one of the light emitting layer 330 , the electron transport layer 340 , and the electron transport auxiliary layer 360 .

According to one example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and optionally may further include an electron transport auxiliary layer. The electron transport layer includes the compound represented by Chemical Formula 1. In this case, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons are easily injected into the electron transport layer from the cathode or electron injection layer due to the compound of Formula 1, and can move quickly from the electron transport layer to the light emitting layer, so that the bonding force between holes and electrons in the light emitting layer increases. high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like. In addition, the compound of Chemical Formula 1 has excellent thermal stability and electrochemical stability, and thus can improve the performance of organic electroluminescent devices.

The compound of Formula 1 may be used alone or in combination with an electron transport layer material known in the art.

In the present invention, the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene ( perylene)-based compounds, aluminum complexes (eg Alq _3, tris(8-quinolinolato)-aluminium), gallium complexes (eg Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), and the like. These may be used alone or in combination of two or more.

In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and may be appropriately adjusted within a range known in the art.

According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer contains the compound represented by Formula 1 include At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound of Chemical Formula 1 has high triplet energy. For this reason, when the compound of Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device may be increased due to a triplet-triplet fusion (TTF) effect. In addition, the compound of Chemical Formula 1 can prevent diffusion of excitons or holes generated in the light emitting layer to the electron transport layer adjacent to the light emitting layer. Accordingly, the number of excitons contributing to light emission in the light emitting layer is increased, so that the light emitting efficiency of the device can be improved, and the lifespan of the device can be effectively increased by improving durability and stability of the device.

The compound represented by Chemical Formula 1 may be used alone or in combination with an electron transport layer auxiliary layer material known in the art.

In the present invention, the auxiliary electron transport layer material that can be mixed with the compound of Formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives (eg , BCP), heterocyclic derivatives containing nitrogen, and the like, but are not limited thereto.

According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer, wherein the light emitting layer is a host and a dopant, and the host may be a compound represented by Formula 1 above. In this case, the light emitting layer of the present invention may include a compound known in the art as a second host in addition to the compound of Formula 1 above.

In the present invention, the content of the host may be about 70 to 99.9% by weight based on the total amount of the light emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light emitting layer.

When the compound represented by Chemical Formula 1 is included as a material for the light emitting layer of the organic electroluminescent device, specifically as a blue, green, or red phosphorescent host material, since the bonding force of holes and electrons in the light emitting layer increases, the efficiency of the organic electroluminescent device ( Luminous efficiency and power efficiency), lifespan, luminance and driving voltage can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Chemical Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material for a high-efficiency light emitting layer.

The structure of the above-described organic electroluminescent device of the present invention is not particularly limited, but, for example, an anode 100, one or more organic material layers 300, and a cathode 200 may be sequentially stacked on a substrate (FIG. 1 to FIG. see 3). In addition, although not shown, an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.

According to one example, the organic electroluminescent device, as shown in Figure 1, on a substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and the cathode 200 may have a sequentially stacked structure. Optionally, as shown in FIG. 2 , an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200 . In addition, an electron transport auxiliary layer 360 may be positioned between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3 ).

In the organic electroluminescent device of the present invention, at least one of the organic material layers 300 (eg, the light emitting layer 330, the electron transport layer 340, or the electron transport auxiliary layer 360) includes the compound represented by Chemical Formula 1. Except for the above, it can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art.

The organic layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

Substrates usable in the present invention are not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead or alloys thereof; and multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the light emitting layer, and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound A-1

[Preparation Example 1-1] Synthesis of 2-bromo-7-phenylspiro [fluorene-9,9'-xanthene]

2,7-dibromospiro[fluorene-9,9'-xanthene] (50g, 102.0mmol, 1eq), phenylboronic acid 12.4g (102.0mmol, 1eq), Pd(PPh ₃ ) ₄ (5.9g, 5.1mmol, 0.05eq ), and K ₂ CO ₃ (28.2g, 204.1mmol, 2eq) were added to 1200ml of Dioxane and 300ml of H ₂ O, followed by heating under reflux for 2 hours. After completion of the reaction, after inactivation with a sufficient amount of water, the solution was transferred to a separatory funnel, and the organic layer was extracted with methylene chloride. Thereafter, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-bromo-7-phenylspiro[fluorene-9,9'-xanthene] (22.4 g, yield 45%).

1H-NMR: δ 8.09 (d, 1H), 7.14 (d, 1H), 7.79 - 7.14 (m, 5H), 7.55 (d, 1H), 7.49 (t, 2H), 7.41 (t, 1H), 7.31 (t, 1H), 7.17 (d, 4H), 6.98 (t, 2H)

Mass : [(M+H) ⁺ ] : 487

[Preparation Example 1-2] Synthesis of Compound A-1

2-bromo-7-phenylspiro[fluorene-9,9'-xanthene] (22.4g, 46.0mmol, 1eq), 4,4,4',4',5,5,5',5'-octamethyl-2 ,2'-bi(1,3,2-dioxaborolane) (11.7g, 46.0mmol, 1eq), Pd(dppf)Cl ₂ (7.0g, 0.05eq), and potassium acetate (29 g, 2eq) were mixed with Dioxane 500 Put into ml and stirred at 110 ℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, and the organic layer was dried over magnesium sulfate, concentrated, and column chromatography was used to obtain the target compound A-1 (19.6 g, yield 80%).

1H-NMR: δ 8.09 (d, 1H), 7.14 (d, 1H), 7.79 - 7.14 (m, 5H), 7.55 (d, 1H), 7.49 (t, 2H), 7.41 (t, 1H), 7.31 (t, 1H), 7.17 (d, 4H), 6.98 (t, 2H), 1.20 (s, 12H)

Mass : [(M+H) ⁺ ] : 536

[Preparation Example 2] Synthesis of Compound A-2

[Preparation Example 2-1] Synthesis of 2-bromo-5-phenyl-9H-fluoren-9-one

Methyl 4-bromo-[1,1':2',1''-terphenyl]-2-carboxylate (50g, 136.2mmol) was dissolved in 500mL of methanesulfonic acid and stirred at room temperature. After the reaction is complete, after cooling to 0 ℃, water is added, the precipitated solid is filtered, dissolved in MC (Dichloromethane), dried over magnesium sulfate, and the resulting compound is purified by column chromatography to obtain 2-bromo-5 -phenyl-9H-fluoren-9-one (27.8 g, yield 64%) was obtained.

1H-NMR: δ 8.44 (d, 1H), 8.15 (d, 1H), 8.10 (s, 1H), 7.80 - 7.71 (m, 5H), 7.46 (t, 2H), 7.38 (t, 1H)

Mass : [(M+H) ⁺ ] : 336

[Preparation Example 2-2] Synthesis of 2-bromo-9-(2-phenoxyphenyl)-5-phenyl-9H-fluoren-9-ol

2-bromo-5-phenyl-9H-fluoren-9-one (27.8g, 83mmol, 1eq) and 250mL of THF were put in a flask under a nitrogen atmosphere, and the mixture was cooled and stirred at -78°C. Thereafter, 30.5 mL of 2.5M n-butyllithium was slowly added dropwise to the flask. After 30 minutes, 1-bromo-2-phenoxybenzene (20.7g, 83mmol, 1eq) was dissolved in 100mL of anhydrous THF and slowly added to the flask, followed by stirring at room temperature for 3 hours. After the reaction was completed, 250 mL of water was added to complete the reaction, extraction was performed with MC, the resulting organic layer was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain the product 2-bromo-9-(2-phenoxyphenyl). )-5-phenyl-9H-fluoren-9-ol (31.4 g, purity 75%) was obtained.

1H-NMR: δ 7.80 - 7.76 (m, 5H), 7.65 (d, 1H), 7.45 - 7.35 (m, 8H), 7.20 - 7.05 (m, 6H)

Mass : [(M+H) ⁺ ] : 506

[Preparation Example 2-3] Synthesis of 2-bromo-5-phenylspiro [fluorene-9,9'-xanthene]

2-bromo-9-(2-phenoxyphenyl)-5-phenyl-9H-fluoren-9-ol (31.4g, 62.2mmol, 1eq), 200mL of acetic acid, and 5.4mL of HCl were mixed and stirred under reflux. After the reaction was completed, the mixture was cooled to room temperature, and 270 mL of water was added thereto, and the resulting solid was filtered. The organic layer obtained by extracting the solid with water and MC was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain the compound 2-bromo-5-phenylspiro[fluorene-9,9'-xanthene] (23.6 g , yield 78%) was obtained.

1H-NMR: δ 7.79 (d, 3H), 7.65 (d, 1H), 7.45 - 7.30 (m, 7H), 7.17 (d, 4H), 7.01 (t, 2H)

Mass : [(M+H) ⁺ ] : 488

[Preparation Example 2-4] Synthesis of Compound A-2

Instead of the 2-bromo-7-phenylspiro [fluorene-9,9'-xanthene] used in [Preparation Example 1-2], 2-bromo-5-phenylspiro [fluorene-9 synthesized in [Preparation Example 2-3] ,9'-xanthene] was used, but Compound A-2 (19.7 g, yield 76%) was obtained in the same manner as in [Preparation Example 1-2].

1H-NMR: δ 7.79 (d, 3H), 7.65 (d, 1H), 7.45 - 7.30 (m, 7H), 7.17 (d, 4H), 7.01 (t, 2H), 1.20 (s, 12H)

Mass : [(M+H) ⁺ ] : 535

[Preparation Example 3] Synthesis of Compound A-3

[Preparation Example 3-1] Synthesis of 9-(2-((4-chlorophenyl)thio)phenyl)-3-phenyl-9H-fluoren-9-ol

3-phenyl-9H-fluoren-9-one (30g, 117.2mmol, 1eq) and 250mL of THF were put in a flask in a nitrogen atmosphere and stirred at -78℃. Thereafter, 36.5 mL of 2.5M n-butyllithium was slowly added dropwise. After 30 minutes, the (2-bromophenyl)(4-chlorophenyl)sulfane (35g, 117.2mmol, 1eq) was dissolved in 150mL of anhydrous THF and slowly added thereto, followed by stirring at room temperature for 3 hours. After the reaction was completed, 300 mL of water was added to terminate the reaction, extraction was performed with MC, the resulting organic layer was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain the product 9-(2-((4-chlorophenyl)thio )phenyl)-3-phenyl-9H-fluoren-9-ol (42.5 g, purity 76%) was obtained.

Mass : [(M+H) ⁺ ] : 478

[Preparation Example 3-2] Synthesis of 2'-chloro-3-phenylspiro [fluorene-9,9'-thioxanthene]

9-(2-((4-chlorophenyl)thio)phenyl)-3-phenyl-9H-fluoren-9-ol (42.5g, 89.1mmol, 1eq), 250mL of acetic acid, and 7.2mL of HCl were added and stirred under reflux. Upon completion of the reaction, the mixture was cooled to room temperature, 400 mL of water was added, and the resulting solid was filtered. The organic layer obtained by extracting the solid with water and MC was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain the compound 2'-chloro-3-phenylspiro[fluorene-9,9'-thioxanthene] (31.1 g, yield 75%) was obtained.

1H-NMR: δ 8.18 (s, 1H), 7.90 (d, 1H), 7.75 - 7.65 (m, 5H), 7.50 - 7.20 (m, 8H), 7.12 (s, 1H), 7.05 (m, 2H)

Mass : [(M+H) ⁺ ] : 460

[Preparation Example 3-3] Synthesis of A-3

2'-chloro-3-phenylspiro[fluorene-9,9'-thioxanthene] (31.1g, 67.8mmol, 1eq) and 4,4,4',4',5,5,5',5'-octamethyl- 2,2'-bi(1,3,2-dioxaborolane) (20.3g, 67.8mmol, 1eq), Pd(dppf)Cl ₂ (9.2g, 0.05eq), potassium acetate (34 g, 2eq), Xhpos ( 3.2g, 0.1eq) was put into 500 ml of Dioxane and stirred at 110 ° C. for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, and the organic layer was dried over magnesium sulfate, concentrated, and column chromatography was used to obtain the target compound A-3 (25.3g, yield 68%).

1H-NMR: δ 8.18 (s, 1H), 7.90 (d, 1H), 7.75 - 7.65 (m, 5H), 7.50 - 7.20 (m, 8H), 7.12 (s, 1H), 7.05 (m, 2H) , 1.20(s, 12H)

Mass : [(M+H) ⁺ ] : 551

[Synthesis Example 1] Synthesis of Compound 1

5g (9.4mmol, 1eq) of Compound A-1 synthesized in Preparation Example 1, 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3, 5-triazine 3.9g (9.4mmol, 1eq), Pd(OAc) ₂ 0.1g (0.5mmol, 0.05eq), XPhos 0.4g (0.9mmol, 0.1eq), and Cs ₂ CO ₃ 6.1g (18.9mmol, 2eq) ) into Toluene 100ml, EtOH 25ml, H ₂ O 25ml and stirred under reflux for 3 hours. After completion of the reaction, after inactivation with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (4.5g, yield 61%).

Mass : [(M+H) ⁺ ] : 793

[Synthesis Example 2] Synthesis of Compound 12

Compound A-2 synthesized in Preparation Example 2 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 2-([1,1'-biphenyl]-3-yl)-4-(3'-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1 instead of 5-triazine, Compound 12 (2.7 g, yield 58%) was obtained in the same manner as in Synthesis Example 1, except that 3,5-triazine was used.

Mass : [(M+H) ⁺ ] : 868

[ synthesis example 3] Synthesis of Compound 16

2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(4'-chloro[1,1'-biphenyl] Compound 16 (4.4g, yield 60%) was obtained in the same manner as in Synthesis Example 1, except that ]-3-yl)-4,6-diphenyl-1,3,5-triazine was used.

Mass : [(M+H) ⁺ ] : 792

[Synthesis Example 4] Synthesis of Compound 27

Compound A-2 synthesized in Preparation Example 2 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 2-(4''-chloro-[1,1':4',1''-terphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 5-triazine Compound 27 (4.1 g, yield 55%) was obtained in the same manner as in Synthesis Example 1, except for the above.

Mass : [(M+H) ⁺ ] : 869

[Synthesis Example 5] Synthesis of Compound 46

Instead of 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine Compound 46 (3.0 g, yield 41%) was obtained in the same manner as in Synthesis Example 1, except that biphenyl] -4-yl) -2,6-diphenylpyrimidine was used.

Mass : [(M+H) ⁺ ] : 792

[Synthesis Example 6] Synthesis of Compound 57

Compound A-2 synthesized in Preparation Example 2 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 Instead of 5-triazine, 4-([1,1'-biphenyl]-3-yl)-2-(3'-chloro-[1,1'-biphenyl]-3-yl)-6-phenylpyrimidine was used. Except, compound 57 (3.5g, yield 47%) was obtained in the same manner as in Synthesis Example 1.

Mass : [(M+H) ⁺ ] : 868

[ synthesis example 7] Synthesis of Compound 61

4-(4'-chloro[1,1'-biphenyl] instead of 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine Compound 61 (4.1 g, yield 56%) was obtained in the same manner as in Synthesis Example 1, except that ]-3-yl)-2,6-diphenylpyrimidine was used.

Mass : [(M+H) ⁺ ] : 792

[Synthesis Example 8] Synthesis of Compound 72

Compound A-2 synthesized in Preparation Example 2 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 Except for using 4-(4''-chloro-[1,1':4',1''-terphenyl]-4-yl)-2,6-diphenylpyrimidine instead of 5-triazine, the above synthesis example Compound 72 (3.8 g, yield 51%) was obtained in the same manner as in 1.

Mass : [(M+H) ⁺ ] : 868

[Synthesis Example 9] Synthesis of Compound 115

Compound A-3 synthesized in Preparation Example 3 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 Except for using 2-(2'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 5-triazine, the above Synthesis Example Compound 115 (2.2 g, yield 30%) was obtained in the same manner as in 1.

Mass : [(M+H) ⁺ ] : 809

[Synthesis Example 10] Synthesis of Compound 130

Compound A-3 synthesized in Preparation Example 3 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 5-triazine Compound 130 (2.4 g, yield 32%) was obtained in the same manner as in Synthesis Example 1, except for the above.

Mass : [(M+H) ⁺ ] : 885

[Synthesis Example 11] Synthesis of Compound 160

Compound A-3 synthesized in Preparation Example 3 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 Compound 160 ( 2.7 g, yield 36%) was obtained.

Mass : [(M+H) ⁺ ] : 809

[Synthesis Example 12] Synthesis of Compound 175

Compound A-3 synthesized in Preparation Example 3 was used instead of Compound A-1, and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3 Except for using 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenylpyrimidine instead of 5-triazine, the above synthesis example Compound 175 (3.0 g, yield 40%) was obtained in the same manner as in 1.

Mass : [(M+H) ⁺ ] : 884

[Example 1] Fabrication of blue organic electroluminescent device

After subjecting Compound 1 to high-purity sublimation purification by a commonly known method, a green organic EL device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., and drying, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then clean the substrate for 5 minutes using UV and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Solus Advanced Materials Co., Ltd., 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Solus Advanced Materials Co., Ltd., 30 nm) / Compound 1 (30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to fabricate an organic electroluminescent device. The structures of NPB and ADN used at this time are as follows.

[Examples 2 to 12] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the electron transport layer materials in Table 1 was used instead of Compound 1 used as the electron transport layer material.

[Comparative Example 1] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of Compound 1 used as the electron transport layer material. The structure of Alq ₃ used at this time is as follows.

[Comparative Example 2] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1 used as the electron transport layer material was not used.

[Comparative Example 3] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound X-1 was used instead of Compound 1 used as the electron transport layer material.

[Comparative Example 4] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound X-2 was used instead of Compound 1 used as the electron transport layer material.

[Comparative Example 5] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound X-3 was used instead of Compound 1 used as the electron transport layer material.

[Comparative Example 6] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound X-4 was used instead of Compound 1 used as the electron transport layer material.

[Comparative Example 7] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound X-5 was used instead of Compound 1 used as the electron transport layer material.

[Evaluation Example 1]

For the blue organic electroluminescent devices prepared in Examples 1 to 12 and Comparative Examples 1 to 7, driving voltage, emission peak and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. showed up

Sample electron transport layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 compound 1 3.4 455 8.0 Example 2 compound 12 3.3 454 8.0 Example 3 compound 16 3.2 456 7.9 Example 4 compound 27 3.4 454 8.0 Example 5 compound 46 3.1 455 7.8 Example 6 compound 57 3.3 454 8.1 Example 7 compound 61 3.2 454 7.9 Example 8 compound 72 3.3 455 8.0 Example 9 compound 115 3.3 454 8.2 Example 10 compound 130 3.2 455 8.1 Example 11 compound 160 3.4 455 8.1 Example 12 compound 175 3.3 454 8.0 Comparative Example 1 Alq ₃ 4.6 457 5.6 Comparative Example 2 - 4.7 459 6.1 Comparative Example 3 X-1 3.8 455 6.2 Comparative Example 4 X-2 3.8 456 6.3 Comparative Example 5 X-3 3.8 455 6.1 Comparative Example 6 X-4 3.9 455 6.2 Comparative Example 7 X-5 3.9 455 6.2

As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 12 using the compound of the present invention as an electron transport layer material are conventional blue organic electroluminescent devices of Comparative Example 1 using Alq ₃ as an electron transport layer material. and an electron transport layer, compared to the blue organic light emitting device of Comparative Example 2, which did not include the electron transport layer, it was found to exhibit significantly better performance in terms of driving voltage, emission peak, and current efficiency.

In addition, the blue organic light emitting devices of Examples 1 to 12 have a structure similar to that of the compound of Formula 1 according to the present invention, and compounds X-1 to X-4 in Formula 1 in which Ar ₁ is hydrogen are used as electron transport layer materials, respectively. Compared to the blue organic light emitting diodes of Comparative Examples 3 to 6 used, it was confirmed that current efficiency and driving voltage characteristics were significantly improved.

In addition, the blue organic electroluminescent devices of Examples 1 to 12 have a structure similar to the compound of Formula 1 according to the present invention, but compound X-5 in which a spyro moiety and an azine moiety are bonded through a phenylene group is formed by electron Compared to the blue organic light emitting device of Comparative Example 7 used as the transport layer material, it was confirmed that current efficiency and driving voltage characteristics were significantly improved.

[ Example 12] blue organic electric field Fabrication of light emitting device

After subjecting Compound 1 to high-purity sublimation purification by a conventionally known method, a blue organic electroluminescent device was manufactured according to the following procedure.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After the distilled water cleaning is finished, ultrasonic cleaning is performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then clean the substrate for 5 minutes using UV and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Solus Advanced Materials Co., Ltd., 30 nm) / Compound 1 (5 nm) / Alq ₃ ( 25 nm) / LiF (1 nm) / Al (200 nm) in this order to prepare an organic electroluminescent device. The structures of NPB, ADN and Alq ₃ used at this time are as follows.

[Examples 14 to 24] - Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except for using each of the electron transport auxiliary layer materials in Table 2 instead of Compound 1 used as the electron transport auxiliary layer material.

[Comparative Example 8] - Preparation of blue organic electroluminescent device

Fabrication of a blue organic electroluminescent device in the same manner as in Example 13, except that the electron transport layer material Alq ₃ was deposited at 30 nm instead of 25 nm without using Compound 13 used as the electron transport auxiliary layer material. did

[Comparative Example 9] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound X-1 was used instead of Compound 1 used as the electron transport auxiliary layer material. The structure of the compound X-1 used at this time is the same as that described in Comparative Example 3, so it is omitted.

[Comparative Example 10] - Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound X-2 was used instead of Compound 1 used as the electron transport auxiliary layer material. The structure of the compound X-2 used at this time is the same as that described in Comparative Example 4, so it is omitted.

[Comparative Example 11] - Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound X-3 was used instead of Compound 1 used as the electron transport auxiliary layer material. The structure of the compound X-3 used at this time is the same as that described in Comparative Example 5, so it is omitted.

[Comparative Example 12] - Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound X-4 was used instead of Compound 1 used as the electron transport auxiliary layer material. The structure of the compound X-4 used at this time is the same as that described in Comparative Example 6, so it is omitted.

[Comparative Example 13] - Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound X-5 was used instead of Compound 1 used as the electron transport auxiliary layer material. The structure of the compound X-5 used at this time is the same as that described in Comparative Example 7, so it is omitted.

[Evaluation Example 2]

For the blue organic EL devices prepared in Examples 13 to 24 and Comparative Examples 8 to 13, driving voltage, emission peak and current efficiency were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 2 below. showed up

Sample Electron Transport Auxiliary Layer Materials Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 13 compound 1 3.3 455 7.8 Example 14 compound 12 3.3 453 8.0 Example 15 compound 16 3.2 454 8.0 Example 16 compound 27 3.1 453 8.1 Example 17 compound 46 3.3 454 8.0 Example 18 compound 57 3.2 453 8.1 Example 19 compound 61 3.4 455 8.0 Example 20 compound 72 3.3 455 8.0 Example 21 compound 115 3.4 454 8.1 Example 22 compound 130 3.3 452 8.1 Example 23 compound 160 3.4 453 8.3 Example 24 compound 175 3.2 453 8.1 Comparative Example 8 - 4.7 459 6.1 Comparative Example 9 X-1 3.8 455 7.1 Comparative Example 10 X-2 3.8 455 7.0 Comparative Example 11 X-3 3.8 455 7.1 Comparative Example 12 X-4 3.9 455 7.2 Comparative Example 13 X-5 3.9 455 7.0

As shown in Table 2, the blue organic electroluminescent devices of Examples 13 to 24 using the compound of the present invention as the electron transport auxiliary layer material do not use the electron transport auxiliary layer material, and conventional Alq ₃ is used as the electron transport layer material. It was found to be superior in terms of driving voltage and current efficiency compared to the blue organic light emitting device of Comparative Example 8 used as .

In addition, the blue organic electroluminescent devices of Examples 13 to 24 have a structure similar to that of the compound of Formula 1 according to the present invention, but the compounds X-1 to X-4 in Formula 1 in which Ar ₁ is hydrogen are used as electron transport auxiliary layers, respectively. Compared to the blue organic light emitting diodes of Comparative Examples 9 to 12 used as the material, it was confirmed that the current efficiency and driving voltage characteristics were significantly improved.

In addition, the blue organic electroluminescent devices of Examples 1 to 12 have a structure similar to that of the compound of Formula 1 according to the present invention, but compound X-5 in which a spyro moiety and an azine moiety are bonded through a phenylene group is electron Compared to the blue organic light emitting device of Comparative Example 13 used as the transport auxiliary layer material, it was confirmed that the current efficiency and driving voltage characteristics were significantly improved.

100: anode, 200: cathode,
300: organic material layer, 310: hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer,
360: electron transport auxiliary layer

Claims (10)

A compound represented by Formula 1 below:
[Formula 1]

X is O or S;
m1 and m2 are each 0 or 1, provided that m1+m2=1,
A is a substituent represented by Formula 2 below,
[Formula 2]

n is 2 or 3;
Z ₁ to Z ₃ are the same as or different from each other, and are each independently N or C(R ₃ ), provided that at least one of Z ₁ to Z ₃ is N, where C(R ₃ ) is plural, plural R ₃ of are the same as or different from each other,
R ₁ to R ₃ are the same as or different from each other, and are each independently hydrogen, deuterium, tritium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~C ₄₀ alkyl group, 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 ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ selected from the group consisting of arylamine group, or condensation by combining with adjacent groups form a ring,
a is an integer from 1 to 8;
A plurality of Ar ₁ are the same as or different from each other;
Ar ₁ is C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group And C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,
An alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, and an alkylboron of R ₁ to R ₃ and Ar ₁ Group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group , C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 ~ C ₆₀ Arylboron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ Arylphosphine oxide group, C ₆ ~ C ₆₀ Substituted with one or more substituents selected from the group consisting of arylamine group or unsubstituted, and when the substituents are plural, they are the same as or different from each other). According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 3 to 6:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

(In Chemical Formulas 3 to 6,
X, n, R ₁ , R ₂ , Ar ₁ and Z ₁ to Z ₃ are each as defined in claim 1,
a1 is an integer from 0 to 4;
a2 is an integer from 0 to 3). According to claim 1,
In Formula 2,

A compound wherein the moiety is selected from the group consisting of the following linker groups L-1 to L-12:

. According to claim 1,
In Formula 2,

A compound wherein the moiety is any one of the following substituents Az1 to Az3:

. According to claim 1,
Wherein R ₁ and R ₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, tritium, and C ₆ ~ C ₆₀ aryl groups;
The aryl group of R ₁ and R ₂ is deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl groups, C ₁ ~ C ₄₀ alkyl groups, C ₆ ~ C ₆₀ aryl groups, 5 to 60 nuclear atoms heteroaryl groups, C ₁ ~ C ₄₀ alkyloxy groups, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ An arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group substituted or unsubstituted with one or more substituents selected from the group consisting of, and when the substituents are plural, they are mutually A compound that is the same or different. According to claim 1,
a is 1,
Ar ₁ is an aryl group of C ₆ to C ₆₀ ;
Aryl group of Ar ₁ is deuterium, halogen, cyano group, nitro group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, 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 Group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphos substituted or unsubstituted with one or more substituents selected from the group consisting of a pin group, a C ₆ ~ C ₆₀ arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, and when the substituents are plural, they are the same as or different from each other which is, a compound. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 7 to 22:
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

(In Chemical Formulas 7 to 22,
X, n, R ₁ , R ₂ , Ar ₁ and Z ₁ to Z ₃ are each as defined in claim 1). According to claim 1,
The compound represented by Formula 1 is any one of the following compounds 1 to 180, a compound:

. anode; cathode; Including one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers includes an organic electroluminescent device comprising the compound according to any one of claims 1 to 8. According to claim 9,
The organic material layer containing the compound is at least one selected from the group consisting of a light emitting layer, an electron transport layer and an electron transport auxiliary layer, an organic electroluminescent device.

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