KR102198515B1 - Organic light-emitting compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel condensed phenanthrene-based compound having excellent electron transport ability and luminescence ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer.

Description

Organic light-emitting compound and organic electroluminescent device including the same {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device including the same, and more particularly, a novel condensed phenanthrene-based compound having excellent hole injection and transport capabilities, and light emission capabilities, and the same as a material of one or more organic material layers. Accordingly, it relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as ``organic EL devices'') followed by blue electroluminescence using an anthracene single crystal in 1965 from the observation of Bernanose's organic thin-film emission in the 1950s. In 1987, Tang proposed an organic EL device having a stacked structure divided into a hole layer and a functional layer of a light emitting layer. Since then, in order to make a high-efficiency, high-life organic EL device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.

The material 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 emission color. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material can be classified 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 four times compared to fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

To date, the hole injection layer and the hole transport layer. As the hole blocking layer and the electron transport layer, NPB, BCP, Alq ₃ and the like represented by the following formula are widely known, and anthracene derivatives as a light emitting material are reported as fluorescent dopant/host materials. In particular, as phosphorescent materials that have 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 blue, green, and red dopants. It is being used as a material. Until now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, conventional host materials have an advantage in terms of light emission characteristics, but have low glass transition temperatures and very poor thermal stability, so they are not at a satisfactory level in terms of lifespan in an organic EL device.

An object of the present invention is to provide a novel organic compound excellent in both hole injection and transport capabilities, and luminescence capabilities.

In addition, another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, exhibiting a low driving voltage and high luminous efficiency, and an improved lifespan.

In order to achieve the above object, the present invention provides a compound represented by the following Formula 1 or Formula 2.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (3) ( fused) to form a condensed ring;

[Formula 3]

In Chemical Formula 3,

The dotted line is a part in which condensation is performed with Formula 1 or Formula 2;

In Chemical Formulas 1 to 3,

X ₁ and X ₄ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ), and , Preferably at least one of X ₁ and X ₄ is N(Ar ₁ ), more preferably X ₁ is selected from O, S, N(Ar ₁ ), and X ₄ is N(Ar ₁ );

X ₂ and X ₃ are the same as or different from each other, and each independently N or C(R ₉ ), preferably both X ₂ and X ₃ are C(R ₉ ) or X ₂ is C(R ₉ ) , X ₃ may be N;

Y ₁ to Y ₄ are the same as or different from each other, and each independently N or C (R ₁₀ ), for example, all of Y ₁ to Y ₄ C (R ₁₀ ) or at least one of Y ₁ to Y ₄ is N Can be;

R ₁ to R ₁₀ that do not form condensation with the ring represented by Formula 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C _Consisting of ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group and C ₆ ~ C ₆₀ arylamine group It may be selected from the group or combined with an adjacent group to form a condensed ring;

Ar ₁ to Ar ₇ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ 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 ₆ ~ C ₆₀ is selected from the group consisting of mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of the R ₁ to R ₁₀ and Ar ₁ to Ar ₇ A boron group, arylphosphine group, mono or diarylphosphinyl group, and arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atom heteroaryl group, C ₁ to C ₄₀ Alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group of, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group substituted or provided with one or more substituents selected from the group consisting of When cyclic and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁ to R ₁₀ and Ar ₁ to Ar ₇ which do not form condensation with the ring represented by Formula 3 in Formulas 1 and 2 are the same or different from each other, and the R At least one of ₁ to R ₁₀ and Ar ₁ to Ar ₇ is a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine Is selected from the group consisting of groups;

The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are each independently deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alke Nyl 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, 5 to 60 nuclear atoms heteroaryl group , C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ one or more aryl group consisting of an amine group of the C ₆₀ of the When substituted with a substituent or unsubstituted with a plurality of substituents, they may be the same or different from each other.

In addition, according to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ that does not form condensation with the ring represented by Formula 3 in Formulas 1 and 2 is a phenyl group or the following It is characterized by being a substituent represented by Chemical Formula 4.

[Formula 4]

In Chemical Formula 4,

* Means a moiety bonded to Formula 1 or Formula 2;

L is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C(R ₁₁ ), preferably at least one of Z ₁ to Z ₅ is N;

When R ₁₁ is plural, they are the same or different from each other, and the R ₁₁ are each independently hydrogen, 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 ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ ~ C ₆₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that Can be combined to form a condensed ring;

Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group of, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ The group consisting of an alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group, and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, they may be the same as or different from each other.

In addition, according to a preferred embodiment of the present invention, the substituent represented by Formula 4 is characterized in that it is selected from the group consisting of substituents represented by Formula A-1 to Formula A-15.

In the above A-1 to A-15,

* Means a moiety bonded to Formula 1 or Formula 2;

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₂ , and when n is 1 to 4, R ₁₂ is each independently deuterium, halogen, cyano group , A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diaryl It is selected from the group consisting of a phosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

Alkyl group of the R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Of alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of an arylborone group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group And, when substituted with a plurality of substituents, they may be the same as or different from each other;

L and R ₁₁ are each as defined in Chemical Formula 4.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ that does not form condensation with the ring represented by Formula 3 in Formula 1 and Formula 2 is represented by the following Formula 5 It is characterized in that it is a substituent.

[Formula 5]

In Chemical Formula 5,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₃ and R ₁₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine group Or, the R ₁₃ and R ₁₄ may be bonded to each other to form a condensed ring;

The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁₃ and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ ~ C ₆₀ of When substituted or unsubstituted, and substituted with a plurality of substituents, they may be the same or different from each other.

In addition, according to a preferred embodiment of the present invention, the compound represented by Formula 1 is characterized in that it is represented by any one of the following Formulas 6 to 11.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Chemical Formulas 6 to 11,

X ₁ to X ₄ , Y ₁ to Y ₄ and R ₁ to R ₈ are each as defined in Formula 1 above.

In addition, according to a preferred embodiment of the present invention, the compound represented by Formula 2 is characterized in that it is represented by any one of Formulas 12 to 17 below.

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Formulas 12 to 17,

X ₁ , X ₄ , Y ₁ to Y _4, Ar ₆ to Ar ₇ and R ₁ to R ₈ are each as defined in Formula 2 above.

In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers One provides an organic electroluminescent device comprising a compound represented by Formula 1 or Formula 2.

Herein, the organic material layer including the compound represented by Formula 1 or Formula 2 may be selected from the group consisting of an electron transport layer, an electron transport auxiliary layer, and an emission layer, and preferably, the organic material layer including the compound may be an emission layer, and more Preferably, the compound may be used as a phosphorescent host, a fluorescent host, or a dopant material for the light emitting layer.

In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched 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 or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.

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

In the present invention, "aryl" refers to 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, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms 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 further, 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, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R means an aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

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 It may include. Examples of the 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, "arylamine" refers to an amine substituted with an aryl having 6 to 60 carbon atoms.

In the present invention, "cycloalkyl" refers to 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" refers to 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 a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, "alkylsilyl" is silyl substituted with alkyl having 3 to 40 carbon atoms, and "arylsilyl" refers to silyl substituted with aryl having 6 to 60 carbon atoms.

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

Since the compound represented by Formula 1 or Formula 2 according to the present invention has excellent thermal stability and light emission properties, it can be used as a material for an organic material layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 or Formula 2 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency and long lifespan compared to conventional host materials is manufactured. In addition, a full-color display panel with improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The present invention provides a novel condensed phenanthrane compound having a higher molecular weight than a conventional material for an organic EL device [eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as'CBP')], and excellent in electron transport ability, hole transport ability, and luminescence ability. to provide.

Specifically, the novel organic compound according to the present invention forms a basic skeleton by condensing any one of an indene moiety, an indole moiety, benzothiophene, benzofuran, and benzosilol to a condensed phenanthrene moiety. It has a structure in which various substituents are bonded to the skeleton.

Preferably, the novel organic compound of the present invention can be represented by the following Formula 1 or Formula 2.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (3) to form a fused ring;

[Formula 3]

In Chemical Formula 3,

The dotted line is a portion where condensation occurs with Formula 1 or Formula 2;

In Chemical Formulas 1 to 3,

X ₁ and X ₄ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ), and , Preferably at least one of X ₁ and X ₄ is N(Ar ₁ ), more preferably X ₁ is selected from O, S, N(Ar ₁ ), and X ₄ is N(Ar ₁ );

X ₂ and X ₃ are the same as or different from each other, and each independently N or C(R ₉ ), in an example, both X ₂ and X ₃ are C(R ₉ ), or X ₂ is C(R ₉ ) And X ₃ may be N;

Y ₁ to Y ₄ are the same as or different from each other, and each independently N or C (R ₁₀ ), for example, all of Y ₁ to Y ₄ C (R ₁₀ ) or at least one of Y ₁ to Y ₄ is N Can be;

R ₁ to R ₁₀ that do not form condensation with the ring represented by Formula 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C _Consisting of ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group and C ₆ ~ C ₆₀ arylamine group It may be selected from the group or combined with an adjacent group to form a condensed ring;

Ar ₁ to Ar ₇ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ 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 ₆ ~ C ₆₀ is selected from the group consisting of mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of the R ₁ to R ₁₀ and Ar ₁ to Ar ₇ A boron group, arylphosphine group, mono or diarylphosphinyl group, and arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atom heteroaryl group, C ₁ to C ₄₀ Alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group of, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group substituted or provided with one or more substituents selected from the group consisting of When cyclic and substituted with a plurality of substituents, they may be the same or different from each other.

The compound represented by Formula 1 or Formula 2 provided in the present invention has a molecular weight higher than that of a conventional material for an organic EL device [eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as'CBP')], while having an electron transport capability, Excellent hole transport and luminous ability. Therefore, when the compound of Formula 1 or Formula 2 is used as an organic material layer material of an organic electroluminescent device, preferably at least one of an electron transport layer material, a hole transport layer material, and a light emitting layer material, the driving voltage and efficiency of the device (luminous efficiency , Current efficiency) and lifespan can be improved.

In general, in the phosphorescent layer of an organic electroluminescent device, the host material must have a triplet energy gap higher than that of the dopant. That is, when the lowest excited state of the host has higher energy than the lowest emission state of the dopant, phosphorescence emission efficiency may be improved. Accordingly, in the present invention, the compound of Formula 1 or Formula 2 may be used as a phosphorescent host material because a specific substituent group is introduced into the basic skeleton having a high triplet energy, so that the energy level can be adjusted higher than the dopant.

In addition, the compound of Formula 1 or Formula 2 may have a wide band gap (sky blue ~ red) by adjusting the energy level according to the substituents bonded to the basic skeleton, and thus, the carrier is easily transferred to the dopant. In addition, excitons formed in the emission layer may be prevented from being transferred (diffused) to the surrounding organic material layer. Accordingly, the compound of Formula 1 or Formula 2 may improve the phosphorescent characteristics of the device compared to the conventional CBP, and at the same time, improve electron and/or hole transport capability, luminous efficiency, driving voltage, life characteristics, and the like.

Further, depending on the substituents, in addition to the host material of the emission layer, it may be applied as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a light emission auxiliary layer, and the like. In particular, the compound of Formula 1 or Formula 2 may have a characteristic of a bipolar compound as a whole depending on the characteristics of the substituent bonded to the basic skeleton. According to an example, when the substituent bonded to the basic skeleton is an electron withdrawing group (EWG) having high electron absorption, the compound of Formula 1 or Formula 2 has bipolar, and thus, not only has a wide band gap. , It is possible to increase the bonding force between holes and electrons. Accordingly, the compound of the present invention can improve the phosphorescent property of the organic EL device and at the same time improve the hole injection ability, transport ability, or luminous efficiency.

In addition, the compound of Formula 1 or Formula 2 introduces various aromatic ring substituents into the basic skeleton, thereby significantly increasing the molecular weight of the compound, thereby increasing the glass transition temperature, resulting in higher thermal than conventional CBP. It can have stability. Accordingly, the organic electroluminescent device including the compound represented by Chemical Formula 1 or Chemical Formula 2 of the present invention can greatly improve durability and lifespan characteristics.

As described above, when the compound represented by Formula 1 or Formula 2 of the present invention is used as a material for a hole injection layer, a hole transport layer, or a light emitting layer of an organic electroluminescent device, the organic electric field is compared to a conventional organic material layer material (eg, CBP). It is possible to improve the efficiency and life of the light emitting device. In addition, the improvement of the lifetime of the organic electroluminescent device can maximize the performance of the full-color organic light emitting panel.

According to a preferred embodiment of the present invention, in consideration of a wide band gap, light emission characteristics, and thermal stability, R ₁ to R ₁₀ which do not form condensation with the ring represented by Chemical Formula 3 in Chemical Formulas 1 and 2, and Ar ₁ to Ar ₇ are the same as or different from each other, and at least one is a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ aryl It is preferably selected from the group consisting of amine groups.

At this time, the alkyl group, aryl group, heteroaryl group and arylamine group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are each independently deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ Alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, hetero with 5 to 60 nuclear atoms Aryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl Selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphine group and a C ₆ ~ C ₆₀ arylamine group When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they may be the same as or different from each other.

In addition, according to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ that does not form condensation with the ring represented by Formula 3 in Formulas 1 and 2 is a phenyl group or the following It is characterized by being a substituent represented by Chemical Formula 4.

[Formula 4]

In Chemical Formula 4,

* Means a moiety bonded to Formula 1 or Formula 2;

L is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C(R ₁₁ ), preferably at least one of Z ₁ to Z ₅ is N;

When R ₁₁ is plural, they are the same or different from each other, and the R ₁₁ are each independently hydrogen, 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 ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ ~ C ₆₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that Can be combined to form a condensed ring;

Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group of, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ The group consisting of an alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group, and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, they may be the same as or different from each other.

In addition, according to a preferred embodiment of the present invention, the substituent represented by Formula 4 is characterized in that it is selected from the group consisting of substituents represented by Formula A-1 to Formula A-15.

In Formulas A-1 to A-15,

* Means a moiety bonded to Formula 1 or Formula 2;

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₂ , and when n is 1 to 4, R ₁₂ is each independently deuterium, halogen, cyano group , A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diaryl It is selected from the group consisting of a phosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

Alkyl group of the R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Of alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of an arylborone group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group And, when substituted with a plurality of substituents, they may be the same as or different from each other;

L and R ₁₁ are each as defined in Chemical Formula 4.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ that does not form condensation with the ring represented by Formula 3 in Formula 1 and Formula 2 is represented by the following Formula 5 It is characterized in that it is a substituent.

[Formula 5]

In Chemical Formula 5,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₂ is selected from the group consisting of a single bond, an arylene group of C ₆ to C _{18 and} a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₃ and R ₁₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine group Or, the R ₁₃ and R ₁₄ may be bonded to each other to form a condensed ring;

The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁₃ and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ - a group arylboronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ - C ₆₀ When substituted or unsubstituted, and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and At least one of R ₇ and R ₈ is fused with the ring represented by Formula 3 to form a condensed ring, and may be embodied as a compound represented by any one of Formulas 6 to 11, but is limited thereto. no.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Chemical Formulas 6 to 11,

X ₁ to X ₄ , Y ₁ to Y ₄ and R ₁ to R ₈ are as defined in Formula 1, respectively.

In addition, according to a preferred embodiment of the present invention, in the compound represented by Formula 2, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , And any one of R ₇ and R ₈ is condensed with the ring represented by Formula 3 to form a condensed ring, and may be embodied as a compound represented by any one of Formulas 12 to 17, but is not limited thereto. .

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Chemical Formulas 12 to 17,

X ₁ , X ₄ , Y ₁ to Y ₄ , Ar ₆ to Ar ₇ and R ₁ to R ₈ are each as defined in Formula 2 above.

The compound represented by Formula 1 or Formula 2 according to the present invention may be specifically represented by the following formulas, but is not limited thereto.

The compound of Formula 1 or Formula 2 of the present invention can be synthesized according to a general synthesis method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described later.

2. Organic EL device

Meanwhile, another aspect of the present invention provides an organic electroluminescent device (organic EL device) including the compound represented by Formula 1 or Formula 2 described above.

Specifically, the organic electroluminescent device according to the present invention includes (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, , At least one of the organic material layers includes a compound represented by Formula 1 or Formula 2. In this case, the compound represented by Formula 1 or Formula 2 may be used alone or in combination of two or more.

According to an example of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 or Formula It may contain a compound represented by 2.

Preferably, the organic material layer including the compound of Formula 1 or Formula 2 may be selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, more preferably a light emitting layer.

In particular, when the compound represented by Formula 1 or Formula 2 is included in the organic electroluminescent device as a light emitting layer material, it is expected to improve the luminous efficiency, luminance, power efficiency, thermal stability, and lifespan of the organic electroluminescent device.

For example, the compound represented by Formula 1 or Formula 2 may be used as a phosphorescent host or a fluorescent host of the emission layer, or a dopant material thereof.

Preferably, the compound represented by Formula 1 or Formula 2 may be included in the organic light-emitting device as a blue, green and/or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and for example, an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be

Specifically, the organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate, and if necessary, an electron injection layer is formed on the electron transport layer. May be located.

At this time, at least one of the electron transport layer, the hole transport layer, and the emission layer may include a compound represented by Chemical Formula 1 or Chemical Formula 2, and preferably, the emission layer may include a compound represented by Chemical Formula 1 or Chemical Formula 2, wherein The compound of Formula 1 or Formula 2 may be used as a phosphorescent host or an electron transport layer of the emission layer.

In addition, the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the emission layer and the electron transport layer. At this time, the compound of Formula 1 or Formula 2 may be used as a life improvement layer or an auxiliary electron transport layer.

The organic electroluminescent device of the present invention is manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one of the organic material layers is formed to include the compound of Formula 1 or Formula 2. Can be.

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

In the present invention, the substrate that can be used in the manufacture of the organic electroluminescent device is not particularly limited, and includes, for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or sheet, but is not limited thereto.

Further, 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 and polyaniline; Or carbon black, but is not limited thereto.

In addition, examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; And a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

In addition, the hole injection layer material, the hole transport layer material, the electron injection layer material, and the electron transport layer material 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 merely illustrative of the present invention, and the present invention is not limited by the following examples.

In the preparation examples described below, a schematic reaction scheme used in synthesizing Cores I to VI is as follows.

[Core Synthesis Scheme I & II]

[Core Synthesis Scheme III & IV]

[Core Synthesis Scheme V & VI]

[Preparation Example 1] Synthesis of Core I

<Step 1> Synthesis of 3-bromophenanthrene-9,10-dione

1.0 L of AcOH was added to 50 g (0.24 mol) of phenanthrene-9,10-dione. The reaction solution was heated to reflux for 1 hour, and 5.8 g (0.024 mol) of dibenzoylperoxide was added. After heating the reaction solution for 1 hour, bromine 37 mL (0.72 mol) was slowly added dropwise. The mixture was heated to reflux for 4 hours, cooled to room temperature, and stirred for 12 hours. The resulting solid was filtered under reduced pressure and dried with air. The obtained solid was recrystallized with 300 mL of dimethylformamide to obtain 40.0 g (yield 58%) of the title compound.

¹ H-NMR (300Mz, DMSO-d6): δ 8.51 (s, 1H), 8.35 (d, 1H), 8.00 (d, 1H), 7.79 (d, 1H), 7.75 (t, 1H), 7.74 ( dd, 1H), 7.55 (t, 1H)

[LCMS]: 287

<Step 2> Synthesis of 6-bromo-1,2-diphenyl-1H-phenanthro[9,10-d]imidazole

In the reactant 3-bromophenanthrene-9,10-dione 40.0 g (0.14 mol), aniline 51.9 g (0.56 mol), benzaldehyde 16.3 g (0.153 mol), ammonium acetate 43.0 g (0.56 mol) AcOH 800 mL Added. The reaction solution was heated to reflux at 110° C. for 12 hours, and the temperature was cooled to room temperature. Neutralized with 500 mL of NaOH aqueous solution, extracted with 2.0 L of EA, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 52.0 g (yield 83%) of the title compound.

¹ H-NMR (300Mz, DMSO-d6): δ 9.10 (dd, 1H), 8.93 (dd, 1H), 8.65 (dd, 1H), 7.90 (m, 1H), 7.70 (m, 5H), 7.58 ( m, 2H), 7.54 (dd, 1H), 7.35 (m, 4H), 7.06 (m, 1H)

[LCMS]: 449

<Step 3> 1,2-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[9,10 Synthesis of -d]imidazole

6-bromo-1,2-diphenyl-1H-phenanthro[9,10-d]imidazole 52.0 g (0.12 mol), 4,4,4',4',5,5, 5',5 1.0 L of dioxane was added to 38.2 g (0.15 mol) of'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane). Pd(dppf)Cl ₂ 4.7 g (5.9 mmol) and KOAc 34.1 g (0.35 mol) were added to the reaction solution. The mixture was heated to reflux at 130° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of aqueous ammonium chloride solution in the reaction solution. The mixed solution was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 41.4 g of the title compound (72% yield).

¹ H-NMR (300Mz, DMSO-d6): δ 9.11 (s, 1H), 8.84 (d, 1H), 8.70 (d, 1H), 8.03 (d, 1H), 7.71 (m, 5H), 7.60 ( m, 3H), 7.37 (m, 4H), 7.08 (d, 1H), 1.40 (s, 12H)

[LCMS]: 496

<Step 4> Synthesis of 6-(2-nitrophenyl)-1,2-diphenyl-1H-phenanthro[9,10-d]imidazole

1,2-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[9,10-d] already Toluene 800 mL, EtOH 200 mL, and H ₂ O 200 mL were added to 41.0 g (82.6 mmol) of dazole and 20.0 g (99.1 mmol) of 1-bromo-2-nitrobenzene. Pd(PPh ₃ ) ₄ 4.8 g (4.1 mmol) and K ₂ CO ₃ 34.2 g (248 mmol) were added and heated to reflux at 120° C. for 6 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. The mixture was extracted with 500 mL of EA, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 34.5 g (yield 85%) of the title compound.

¹ H-NMR (300Mz, DMSO-d6): δ 8.90 (m, 1H), 8.72 (t, 1H), 8.08 (dd, 1H), 7.82 (m, 1H), 7.71 (m, 8H), 7.60 ( m, 2H), 7.48 (m, 1H), 7.37 (m, 5H), 7.11 (t, 1H)

[LCMS]: 491

<Step 5> Core I Synthesis of

6-(2-nitrophenyl)-1,2-diphenyl-1H-phenanthro[9,10-d]imidazole 34 g (69.8 mmol) and triphenylphosphine 54.4 g (208 mmol) 1,2 -600 mL of dichlorobenzene was added. The reaction solution was heated to reflux at 200° C. for 12 hours. The reaction solution was cooled to room temperature, 500 mL of purified water was added to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 14.0 g (yield 44%) of the title compound.

¹ H-NMR (300Mz, DMSO-d6): δ 11.91 (s, 1H), 9.29 (m, 1H), 8.52 (m, 1H), 8.15 (d, 1H), 8.13 (d, 1H), 7.85 ( m, 2H), 7.81 (d, 1H), 7.31 (m, 5H), 7.60 (m, 2H), 7.46 (t, 1H), 7.38 (m, 3H), 7.24 (t, 1H), 7.05 (d , 1H)

[LCMS]: 459

[Preparation Example 2] Synthesis of Core II

The same procedure as in Steps 1 to 5 of Preparation Example 1 was performed to obtain 9.0 g (yield 28%) of the target compound.

¹ H-NMR (300Mz, DMSO-d6): δ 11.95 (s, 1H), 9.32 (d, 1H), 8.68 (d, 1H), 8.55 (d, 1H), 8.27 (d, 1H), 7.84 ( d, 1H), 7.72 (m, 6H), 7.62 (m, 2H), 7.48 (t, 1H), 7.35 (m, 4H), 7.26 (m, 2H)

[LCMS]: 459

[Preparation Example 3] Synthesis of Core III

<Step 1> Synthesis of (Z)-3-bromo-10-(hydroxyimino)phenanthrene-9(10H)-one

1.0 L of EtOH was added to 50.0 g (0.17 mol) of 3-bromophenanthrene-9,10-dione, 12.1 g (0.17 mol) of hydroxylamine and 35.1 mL (0.44 mol) of pyridine. The reaction solution was heated to reflux at 100° C. for 12 hours. The reaction solution was cooled to room temperature, and the resulting solid was filtered under reduced pressure, washed with purified water, and then dried with hot air to obtain 40.5 g (yield 77%) of the target compound.

[LCMS]: 302

<Step 2> Synthesis of 6-bromo-2-phenylphenanthro[9,10-d]oxazole

800 mL of DMF was added to 40.0 g (0.13 mol) of (Z)-3-bromo-10-(hydroxyimino)phenanthrene-9(10H)-one and 36.6 g (0.26 mol) of K ₂ CO ₃ . Benzyl bromide 23.6 mL (0.20 mol) was slowly added dropwise to the reaction solution. After stirring at room temperature for 12 hours, 500 mL of purified water was added to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 30.8 g (62% yield) of the title compound.

[LCMS]: 374

<Step 3> 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenanthro[9,10-d]oxazole synthesis

The target compound 27.0 was carried out in the same manner as in Step 3 of Preparation Example 1, except that 30.0 g (80.2 mmol) of 6-bromo-2-phenylphenanthro[9,10-d]oxazole was used as the reactant. g (yield 80%) was obtained.

[LCMS]: 421

<Step 4> Synthesis of 6-(2-nitrophenyl)-2-phenylphenanthro [9,10-d]oxazole

2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenanthro[9,10-d]oxazole 27.0 g ( 64.1 mmol) was used, and 22.7 g of the title compound (yield 85%) was obtained by performing the same procedure as in Step 4 of Preparation Example 1.

[LCMS]: 416

<Step 5> Core III Synthesis of

The same procedure as in Step 5 of Preparation Example 1 was performed, except that 22.0 g (52.8 mmol) of 6-(2-nitrophenyl)-2-phenylphenanthro[9,10-d]oxazole was used as the reactant. Thus, 8.0 g (yield 39%) of the target compound was obtained.

[LCMS]: 384

[Preparation Example 4] Synthesis of Core IV

7.4 g (yield 36%) of the target compound was obtained by performing the same procedure as in Steps 1 to 5 of Preparation Example 3.

[LCMS]: 384

[Preparation Example 5] Synthesis of Core V

<Step 1> Synthesis of 6-bromo-2,2-dimethylphenanthro[9,10-d][1,3]dioxole

To 50 g (0.17 mol) of 3-bromophenanthrene-9,10-dione and 72.2 g (0.52 mol) of K ₂ CO ₃ was added 3.0 L of ACN, THF, H ₂ O mixed solvent (1: 1: 1) I did. 155 g (1.74 mol) of 2-nitropropane was added to the reaction solution and heated to reflux for 12 hours. The reaction was terminated by adding 1.5 L of purified water, extracted with 3.0 L of EA, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 41.3 g (72% yield) of the title compound.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.79 (s, 1H), 8.57 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H), 7.70 (m, 1H), 7.64 (t , 1H), 7.55 (t, 1H), 1.85 (s, 6H)

[LCMS]: 329

<Step 2> 2-(2,2-dimethylphenanthro[9,10-d][1,3]dioxol-6-yl)-4,4,5,5-tetramethyl-1,3,2 -Synthesis of dioxaborolane

Except for using 6-bromo-2,2-dimethylphenanthro[9,10-d][1,3]dioxole as a reactant, the target compound was carried out in the same manner as in Step 3 of Preparation Example 1 35.1 g (75% yield) was obtained.

¹ H-NMR (300Mz, CDCl ₃ ): δ 9.04 (s, 1H), 8.79 (d, 1H), 7.88 (d, 1H), 7.82 (m, 2H), 7.67 (t, 1H), 7.62 (t , 1H), 1.81 (s, 6H), 1.34 (s, 12H)

[LCMS]: 376

<Step 3> Synthesis of 2,2-dimethyl-6-(2-nitrophenyl)phenanthro[9,10-d][1,3]dioxole

2-(2,2-dimethylphenanthro[9,10-d][1,3]dioxol-6-yl)-4,4,5,5-tetramethyl-1,3,2-di as reactant Except that oxaborolane was used, the same procedure as in Step 4 of Preparation Example 1 was performed to obtain 28.3 g of the target compound (82% yield).

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.61 (m, 2H), 7.94 (d, 1H), 7.91 (m, 2H), 7.67 (m, 1H), 7.60 (m, 2H), 7.50 (m , 3H), 1.86 (s, 6H)

[LCMS]: 371

<Step 4> Synthesis of Core V

Except that 2,2-dimethyl-6-(2-nitrophenyl)phenanthro[9,10-d][1,3]dioxol 28.0 g (75.4 mol) was used as a reactant, The same procedure as in Step 5 was performed to obtain 5.0 g of the title compound (20% yield).

[LCMS]: 339

[Preparation Example 6] Synthesis of Core VI

11.6 g (yield 45%) of the target compound was obtained by performing the same procedure as steps 1 to 4 of Preparation Example 5.

¹ H-NMR (300Mz, CDCl ₃ ): δ 9.10 (s, 1H), 8.90 (m, 1H), 8.32 (d, 1H), 8.17 (d, 1H), 8.04 (m, 1H), 7.82 (d , 1H), 7.69 (m, 3H), 7.47 (t, 1H), 7.32 (t, 1H), 1.89 (s, 6H)

[LCMS]: 339

[Synthesis Example 1] Synthesis of Compound 1

DMF 100 mL was added to 6.0 g (13.1 mmol) of the Core I compound of Preparation Example 1 and 4.5 g (17.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine. 0.78 g (19.6 mmol) of 60% NaH was added to the reaction solution. After stirring at room temperature for 12 hours, 100 mL of purified water was added to terminate the reaction. The mixture was extracted with 300 mL of EA and washed twice with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.70 g (yield 52%) of the title compound.

[LCMS]: 690

[Synthesis Example 2] Synthesis of Compound 4

Dioxane 100 mL was added to 4.5 g (9.8 mmol) of the Core I compound of Preparation Example 1 and 5.1 g (14.7 mmol) of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Added. Pd(OAc) ₂ 0.11 g (0.49 mmol), P(t-Bu) ₃ 0.40 g (0.98 mmol), K ₂ CO ₃ 4.1 g (29.4 mmol) were added to the reaction solution and heated to reflux at 120° C. for 12 hours. . The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. The mixed solution was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 3.6 g (yield 48%) of the title compound.

[LCMS]: 766

[Synthesis Example 3] Synthesis of Compound 7

Toluene 100 mL was added to 5.0 g (10.9 mmol) of the Core I compound of Preparation Example 1 and 5.6 g (16.3 mmol) of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine I did. Pd(OAc) ₂ 0.12 g (0.54 mmol), P(t-Bu) ₃ 0.44 g (1.1 mmol), and NaOt-Bu 2.1 g (21.8 mmol) were added to the reaction solution and heated to reflux at 120° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. The mixed solution was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 5.0 g (yield 60%) of the title compound.

[LCMS]: 766

[Synthesis Example 4] Synthesis of Compound 10

5.5 g (12.0 mmol) of the Core I compound of Preparation Example 1 and 7.5 g (18.0 mmol) of 2-(3'-chlorobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine To 100 mL of dioxane was added. Pd(OAc) ₂ 0.13 g (0.60 mmol), XPhos 0.57 g (1.2 mmol), Cs ₂ CO ₃ 7.8 g (23.9 mmol) were added to the reaction solution and heated to reflux at 120° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the reaction solution. The mixed solution was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.0 g (yield 40%) of the title compound.

[LCMS]: 842

[Synthesis Example 5] Synthesis of Compound 11

Toluene 150 mL was added to 7.2 g (16.5 mmol) of the Core I compound of Preparation Example 1 and 2-(4'-chlorobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine I did. Pd ₂ (dba) ₃ 1.4 g (1.6 mmol), BINAP 0.98 g (1.6 mmol), and Cs ₂ CO ₃ 10.2 g (31.3 mmol) were added to the reaction solution and heated to reflux at 120° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of aqueous ammonium chloride solution in the reaction solution. The mixed solution was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 7.3 g (yield 55%) of the title compound.

[LCMS]: 842

[Synthesis Example 6] Synthesis of Compound 16

The same procedure as in Synthesis Example 4 was carried out, except that 4-(3'-chlorobiphenyl-3-yl)-2,6-diphenylpyrimidine was used as a reactant with the Core I compound of Preparation Example 1. Thus, 5.7 g of the target compound (62% yield) was obtained.

[LCMS]: 842

[Synthesis Example 7] Synthesis of Compound 22

Except for using 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine with the Core II compound of Preparation Example 2 as a reactant, the same procedure as in Synthesis Example 2 was performed to Compound 5.3 g (yield 53%) was obtained.

[LCMS]: 766

[Synthesis Example 8] Synthesis of Compound 33

The same procedure as in Synthesis Example 5 was performed, except that the Core II compound of Preparation Example 2 and 2-(4'-chlorobiphenyl-4-yl)-4,6-diphenylpyrimidine were used as reactants. 2.8 g (yield 38%) of the target compound was obtained.

[LCMS]: 842

[Synthesis Example 9] Synthesis of Compound 43

The same procedure as in Synthesis Example 3 was performed, except that the Core III compound of Preparation Example 3 and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine were used as reactants. Thus, 5.6 g of the target compound (yield 52%) was obtained.

[LCMS]: 691

[Synthesis Example 10] Synthesis of Compound 51

The same procedure as in Synthesis Example 5 was carried out, except that the Core III compound of Preparation Example 3 and 2-(4'-chlorobiphenyl-4-ylyl)-4,6-diphenylpyrimidine were used as reactants. Thus, 5.8 g (yield 65%) of the target compound was obtained.

[LCMS]: 766

[Synthesis Example 11] Synthesis of Compound 60

Except for using the Core IV compound of Preparation Example 4 and 4-(3-chlorophenyl)-2,6-diphenylpyrimidine as reactants, the same procedure as in Synthesis Example 2 was performed, and 3.9 g of the target compound (yield 44%).

[LCMS]: 690

[Synthesis Example 12] Synthesis of Compound 71

The same procedure as in Synthesis Example 5 was performed, except that the Core IV compound of Preparation Example 4 and 4-(4'-chlorobiphenyl-3-yl)-2,6-diphenylpyrimidine were used as reactants. 4.4 g (yield 35%) of the target compound was obtained.

[LCMS]: 766

[Synthesis Example 13] Synthesis of Compound 84

Synthesis Example, except that the Core V compound of Preparation Example 5 and 2-(4'-chlorobiphenyl-4-yl)-4,6-diphenyl-1,3,5-triazine were used as reactants. The same procedure as in 5 was performed to obtain 6.1 g (55% yield) of the title compound.

[LCMS]: 722

[Synthesis Example 14] Synthesis of Compound 94

The same procedure as in Synthesis Example 2 was carried out, except that the Core VI compound of Preparation Example 6 and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine were used as reactants. Thus, 4.7 g (yield 53%) of the target compound was obtained.

[LCMS]: 646

[Synthesis Example 15] Synthesis of Compound 100

Synthesis Example, except that the Core VI compound of Preparation Example 6 and 2-(3'-chlorobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine were used as reactants. By following the same procedure as in 4, 3.2 g of the title compound (60% yield) was obtained.

[LCMS]: 722

[Synthesis Example 16] Synthesis of Compound 103

The same procedure as in Synthesis Example 4 was performed, except that the Core VI compound of Preparation Example 6 and 2-(3'-chlorobiphenyl-3-yl)-4,6-diphenylpyrimidine were used as reactants. 5.6 g of the title compound (yield 55%) was obtained.

[LCMS]: 721

[Synthesis Example 17] Synthesis of Compound 108

The same procedure as in Synthesis Example 5 was performed, except that the Core VI compound of Preparation Example 6 and 4-(4'-chlorobiphenyl-4-yl)-2,6-diphenylpyrimidine were used as reactants. 5.3 g (yield 47%) of the target compound was obtained.

[LCMS]: 721

[Example 1] Preparation of blue organic EL device

After the compound Inv-3 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a commonly known method, a blue organic EL device was manufactured according to the following procedure.

The 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, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and 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 (Doosan Electronics, 30 nm)/ Compound 1 (5 nm)/Alq ₃ (25 nm) )/LiF (1 nm)/Al (200 nm) were stacked in order to prepare an organic electroluminescent device.

The structures of NPB, ADN and Alq ₃ used at this time are as follows.

[Example 2] ~ [Example 10] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were respectively used as electron transport auxiliary layer materials instead of compound 1 used in Example 1.

[Comparative Example 1] Preparation of blue organic electroluminescent device

Blue organic EL was carried out in the same manner as in Example 1, except that Compound 1 used as the electron transport auxiliary layer material in Example 1 was not used, and Alq ₃ , which is the electron transport layer material, was deposited at 30 nm instead of 25 nm. The device was fabricated.

[Evaluation Example 1]

For the organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Example 1, respectively, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. Indicated.

Sample Electronic transport auxiliary layer Driving voltage (V) Emission peak (nm) Current efficiency cd/A) Example 1 Compound 1 4.3 442 6.6 Example 2 Compound 4 4.4 448 6.8 Example 3 Compound 7 4.0 445 6.9 Example 4 Compound 10 4.1 440 7.1 Example 5 Compound 22 4.3 456 6.8 Example 6 Compound 43 4.4 458 6.3 Example 7 Compound 60 4.3 455 6.0 Example 8 Compound 84 4.5 458 6.7 Example 9 Compound 94 4.8 459 5.9 Example 10 Compound 100 4.4 458 7.1 Comparative Example 1 - 4.7 458 6.0

As shown in Table 1, the blue organic EL devices of Examples 1 to 10 including an electron transport auxiliary layer formed of the compound according to the present invention are of Comparative Example 1 including an electron transport layer of Alq ₃ without an electron transport auxiliary layer. It was found that compared to the blue organic EL device, it exhibited superior performance in terms of current efficiency and driving voltage.

[Example 11] Fabrication of green organic EL device

Compound 1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

First, the 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, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.

On the prepared ITO transparent electrode, m-MTDATA (60 nm)/TCTA (80 nm)/ 90% of compound 1 + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/ An organic EL device was fabricated by laminating in the order of LiF (1 nm)/Al (200 nm). The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used are as follows.

[Example 12] ~ [Example 20] Preparation of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 11, except that the compound shown in Table 2 below was used instead of the compound 1 used as the light emitting host material when forming the light emitting layer in Example 11.

[Comparative Example 2] Fabrication of green organic EL device

In Example 11, a green organic EL device was manufactured in the same manner as in Example 11, except that CBP was used instead of Compound 1 as a light emitting host material when forming the light emitting layer. The structure of the used CBP is as follows.

[Evaluation Example 2]

For the green organic EL devices each prepared in Examples 11 to 20 and Comparative Example 2, the driving voltage, current efficiency and emission peak at a current density (10) mA/cm2 were measured, and the results are shown in Table 2 below. Indicated.

Sample Host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 11 Compound 4 6.2 513 44.5 Example 12 Compound 10 6.5 516 46.3 Example 13 Compound 11 6.3 519 45.0 Example 14 Compound 16 6.0 520 48.2 Example 15 Compound 22 6.3 515 46.0 Example 16 Compound 33 6.9 510 47.6 Example 17 Compound 51 6.6 512 43.3 Example 18 Compound 71 6.6 525 45.9 Example 19 Compound 84 6.3 514 46.0 Example 20 Compound 94 6.3 518 47.5 Comparative Example 2 CBP 6.9 516 41.5

As shown in Table 2, in the case of the green organic EL device of Examples 11 to 20 using the compound according to the present invention as a light emitting layer material, compared to the green organic EL device of Comparative Example 2 using the conventional CBP, efficiency and driving voltage It was confirmed that this was excellent.

[Example 21] Preparation of red organic EL device

Compound 1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a commonly known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

First, the 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, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.

On the prepared ITO transparent electrode, m-MTDATA (60 nm)/TCTA (80 nm) / 90% compound 1 + 10% (piq) ₂ Ir(acac) (30 nm)/BCP (10 nm)/Alq ₃ (30 nm) )/LiF (1 nm)/Al (200 nm) were stacked in order to fabricate an organic electroluminescent device. The structures of m-MTDATA, TCTA, and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir(acac) is as follows.

[Example 22] to [Example 26] Preparation of red organic EL device

A red organic EL device was manufactured in the same manner as in Example 21, except that the compound shown in Table 3 below was used instead of the compound 1 used as the light emitting host material when forming the light emitting layer in Example 21.

[Comparative Example 3]

A red organic electroluminescent device was manufactured in the same manner as in Example 21, except that CBP was used instead of Compound 1 used as a light emitting host material when forming the emission layer in Example 21. The structure of the used CBP is as described in Comparative Example 2.

[Evaluation Example 3]

For the organic electroluminescent devices prepared in Examples 21 to 26 and Comparative Example 3, respectively, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below.

Sample Host Driving voltage (V) Current efficiency (cd/A) Example 21 Compound 1 4.4 12.5 Example 22 Compound 33 4.6 13.8 Example 23 Compound 60 4.8 11.5 Example 24 Compound 71 4.4 10.8 Example 25 Compound 84 4.3 12.8 Example 26 Compound 103 4.5 11.9 Comparative Example 3 CBP 4.8 10.5

As shown in Table 3, in the case of the red organic EL device of Examples 21 to 26 using the compound according to the present invention as a light emitting layer material, compared to the red organic EL device of Comparative Example 3 using the conventional CBP, efficiency and driving It was confirmed that the voltage was excellent.

Claims (14)

A compound represented by the following Formula 1 or Formula 2:
[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,
At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (3) ( fused) to form a condensed ring;
[Formula 3]

In Chemical Formula 3,
The dotted line is a portion where condensation occurs with Formula 1 or Formula 2;
In Chemical Formulas 1 to 3,
X ₁ and X ₄ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ ), and ;
X ₂ and X ₃ are the same as or different from each other, and each independently N or C(R ₉ );
Y ₁ to Y ₄ are the same as or different from each other, and each independently N or C(R ₁₀ );
R ₁ to R ₁₀ that do not form condensation with the ring represented by Formula 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom number 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C _Consisting of ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group and C ₆ ~ C ₆₀ arylamine group Selected from the group, or combined with adjacent groups to form a condensed ring;
Ar ₁ to Ar ₇ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ 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 ₆ ~ C ₆₀ is selected from the group consisting of mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylamine group;
The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of the R ₁ to R ₁₀ and Ar ₁ to Ar ₇ A boron group, arylphosphine group, mono or diarylphosphinyl group, and arylamine group are each independently 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atom heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ 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 ~ substituted with C ₆₀ or aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the aryl group consisting of an amine group in the C ₆₀ one kind of substituent or is unsubstituted, substituted with a plurality of substituents If so, they are the same or different from each other. The method of claim 1,
At least one of the X ₁ and X ₄ is N (Ar ₁ ), a compound. The method of claim 2,
The X ₁ is selected from the group consisting of O, S and N (Ar ₁ ), X ₄ is N (Ar ₁ ), the compound. The method of claim 1,
R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are the same as or different from each other, at least one of which is a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms And C ₆ ~ C ₆₀ is selected from the group consisting of arylamine group;
The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are each independently deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alke Nyl 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, 5 to 60 nuclear atoms heteroaryl group , C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ one or more aryl group consisting of an amine group of the C ₆₀ of the Compounds characterized in that when substituted or unsubstituted with a substituent and substituted with a plurality of substituents, they are the same or different from each other. The method of claim 1,
At least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ is a phenyl group or a substituent represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
* Means a moiety bonded to Formula 1 or Formula 2;
L is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C(R ₁₁ );
When R ₁₁ is plural, they are the same or different from each other, and the R ₁₁ are each independently hydrogen, 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 ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of arylsilyl group, or adjacent Combines with a group to form a condensed ring;
Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group of, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₃ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ The group consisting of an alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group, and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 5,
A compound characterized in that the substituent represented by Formula 4 is selected from the group consisting of a substituent represented by at least one of the following Formulas A-1 to A-15:

In Formulas A-1 to A-15,
* Means a moiety bonded to Formula 1 or Formula 2;
n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₂ , and when n is 1 to 4, R ₁₂ is each independently deuterium, halogen, cyano group , A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diaryl It is selected from the group consisting of a phosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;
The arylene group, heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine of R ₁₁ and R ₁₂ Group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are 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 ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphine group and C ₆ ~ C ₆₀ arylsilyl When substituted or unsubstituted with one or more substituents selected from the group consisting of groups, and when substituted with a plurality of substituents, they are the same or different from each other,
L and R ₁₁ are as defined in claim 5. The method of claim 1,
At least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ is a compound characterized in that it is a substituent represented by the following formula (5):
[Formula 5]

In Chemical Formula 5,
* Means a moiety bonded to Formula 1 or Formula 2;
L ₂ is selected from the group consisting of a single bond, an arylene group of C ₆ to C _{18 and} a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₃ and R ₁₄ are each independently a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ ~ C ₆₀ arylamine group Or the R ₁₃ and R ₁₄ are bonded to each other to form a condensed ring;
The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁₃ and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ - a group arylboronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ - C ₆₀ When substituted or unsubstituted, and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 1,
The compound represented by Formula 1 is a compound characterized in that it is represented by any one of the following Formulas 6 to 11:
[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Chemical Formulas 6 to 11,
X ₁ to X ₄ , Y ₁ to Y ₄ and R ₁ to R ₈ are each as defined in claim 1. The method of claim 1,
The compound represented by Formula 2 is a compound characterized in that it is represented by any one of the following Formulas 12 to 17:
[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Chemical Formulas 12 to 17,
X ₁ , X ₄ , Y ₁ to Y _4, Ar ₆ to Ar ₇ and R ₁ to R ₈ are each as defined in claim 1. The method of claim 1,
The compound is a compound, characterized in that selected from the group consisting of the following compounds:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic material layers contains the compound according to any one of claims 1 to 10. The method of claim 11,
An organic electroluminescent device, characterized in that the organic material layer containing the compound is selected from the group consisting of an electron transport layer, an electron transport auxiliary layer, and a light emitting layer. The method of claim 12,
An organic electroluminescent device, characterized in that the organic material layer containing the compound is an emission layer. The method of claim 13,
The compound is an organic electroluminescent device used as a phosphorescent host, a fluorescent host, or a dopant material for the emission layer.