KR20220039898A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a compound excellent in thermal stability, electrochemical stability, luminescence ability, and hole transport ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers.

Description

Organic light emitting compound and organic electroluminescent device using same

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

Taking the observation of organic thin film emission by Bernanose in the 1950s as a starting point, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 continued. ) presented an organic electroluminescent device with a stacked structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and when the exciton falls 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, etc. according to their function.

The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing better natural colors according to the emission color. 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 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as the phosphorescent dopant are in progress.

Until now, NPB, BCP, Alq3, etc. are widely known as materials for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as materials for the light emitting layer. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, conventional organic material layer materials are advantageous in terms of light emitting properties, but have not reached a satisfactory level in terms of the lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is not very good. Accordingly, there is a demand for the development of an organic layer material having excellent performance.

The present invention is excellent in heat resistance, carrier transport ability, light emitting ability, electrochemical stability, etc., the organic layer material of the organic electroluminescent device, specifically, a light emitting layer material, a life improvement layer material, a hole injection layer, a hole transport layer light emitting auxiliary layer material, or An object of the present invention is to provide a novel compound that can be used as an electron transport layer material 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 by including the novel compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X is C(R ₅ R ₆ ), O or S;

a to d are each independently an integer of 0 to 4,

R ₁ To R ₆ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C A 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,

However, at least one of R ₁ to R ₄ is represented by the following formula (2),

[Formula 2]

In Formula 2,

* is the part where the bond is made,

n is an integer from 0 to 3,

L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a C 3 to C 18 heteroarylene group,

Ar ₁ and Ar ₂ are the same as or different from each other, and 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, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ Aryl group, Heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ to 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 An aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,

The arylene group of L, heteroarylene group, Ar ₁ to Ar ₂ and R ₁ to R ₆ of the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, arylox Group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine 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 ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₁ to C ₄₀ Alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ 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 Arylamine It is substituted or unsubstituted with one or more substituents selected from the group consisting of a group, and in this case, when the substituents are plural, they are the same or different from each other.

In addition, the present invention is 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, wherein at least among the one or more organic material layers One provides an organic electroluminescent device including the compound represented by Formula 1 above.

Since the compound of the present invention has excellent hole transport ability, hole injection ability, light emitting ability, electrochemical stability, thermal stability, etc., it can be used as an organic material layer material of an organic electroluminescent device.

In particular, when the compound of the present invention is used as at least any one of a light emitting layer material, a life improvement layer material, a light emitting auxiliary layer material, or an electron transport layer material of the light emitting layer, superior light emitting performance, low driving voltage, high efficiency and long lifespan compared to conventional materials An organic EL device having a

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

<New compound>

According to the present invention, the compound represented by Formula 1 is an amine-based moiety (eg, an arylamine group and/or a heteroarylamine group) directly bonded to a benzoxanthine (A)-based core or a separate linker (L ) has a basic skeletal structure connected through

More specifically, the compound of Formula 1 includes a benzoxanthine-based moiety and an amine-based moiety, which are electron donor groups (EDG). As such, by introducing an amine-based moiety, which is a functional group having a strong electron-donating ability, the movement speed of holes is improved, and thus it is possible to have physicochemical properties more suitable for hole injection and hole transport. When the compound of Formula 1 is applied as a hole transport layer material, holes can be well received from the anode and holes can be smoothly transferred to the light emitting layer, thereby lowering the driving voltage of the device and inducing high efficiency and long lifespan. As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.

In particular, the moiety in which benzoanthracene is bonded to benzoxanthine adopted in the present invention has a longer condensation than the conventional compound in which fluorene is bonded to benzoxanthine, which results in a relatively reduced band gap and low LUMO value. . In addition, the compound represented by Formula 1 has a triplet energy value higher than that of a general anthracene-based compound through sp3 bonding of the core compound and control of the bonding position with the linker. Therefore, due to the physicochemical properties, the benzoxanthine-based compound according to the present invention may have high luminous efficiency and long lifespan.

The compound represented by Formula 1 according to the present invention has a basic skeleton structure in which an amine-based moiety and a benzoxanthene (A)-based moiety are located, and these are directly connected or connected through a separate linker (L). .

In the compound represented by Formula 1, X is C(R ₅ R ₆ ), O, or S. The compound of Formula 1 has excellent amphoteric properties of electrons and holes, and thus has excellent carrier transport ability. Therefore, when the compound of Formula 1 according to the present invention is used as a material for the hole transport layer, the effect of improving the efficiency and driving voltage can be improved by improving the hole transport ability.

In addition, in the compound represented by Formula 1, a to c are each independently an integer of 0 to 4, and d is an integer of 0 to 3.

Here, when a to d are each 0, it means that each hydrogen is not substituted with a substituent R ₁ to R ₄ , and when a to d are each an integer of 1 to 4, a plurality of R ₁ to a plurality of R ₄ are same or different from each other

Wherein R ₁ To R ₆ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group.

At this time, at least one of R ₁ to R ₄ is represented by the following formula (2).

[Formula 2]

The substituent represented by Formula 2 is directly connected to a benzoxanthene (A)-based core or is connected through a separate linker (L), which is a type of electron donor group (EDG).

In one embodiment of such an amine-based moiety, Ar ₁ and Ar ₂ are the same as or different from each other, and 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, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ 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 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 may be} selected from the group consisting of. Preferably, Ar ₁ and Ar ₂ are the same as or different from each other, and may each independently be selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

In one embodiment of the present invention, Ar ₁ and Ar ₂ may be the same as or different from each other, and each independently selected from the group of substituents represented by any one of Formulas 3 and 4 may be further specified. However, the present invention is not limited thereto.

[Formula 3]

[Formula 4]

In Formula 3 or 4,

* means a portion where a bond with Formula 2 is formed,

Z is (CR ₇ R ₈ ) or O,

m is an integer from 1 to 3.

Here, R, R ₇ and R ₈ are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, and a C ₂ to C ₄₀ alkenyl group. , C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ May be selected from the group consisting of an arylamine group, these Combined to form a condensed ring.

In a more specific example of the present invention, Ar ₁ and Ar ₂ may be the same as or different from each other, and may be each independently selected from the following structural formula.

In the above formula,

* denotes a portion in which a bond with Chemical Formula 2 is formed.

The amine-based moiety represented by Formula 2 may be directly bonded to a benzoxanthene-based core or may be bonded through a separate linker (L).

The linker (L) may be a linker of a conventional divalent group known in the art. For example, L may be a single bond (eg, a direct bond), or a substituted or unsubstituted C ₆ ~ C ₁₈ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nuclear atoms It may be selected from the group consisting of .

In one embodiment of the present invention, the linker of Formula 2 may be a single bond or a linker selected from the following structural formulas.

In the above formula,

* denotes a portion at which a bond with Chemical Formula 1 is formed.

Although the above-mentioned linker (L) is not specifically shown in the formula, at least one or more substituents known in the art (eg, R ₁ ) may be substituted.

n is an integer from 0 to 3.

In Formula 1 of the present invention, the arylene group, heteroarylene group, Ar ₁ to Ar ₂ and R ₁ to R ₆ of L is an arylene group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group , an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine 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 ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ Aryl group, nuclear atom number 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ May be substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group.

The compound represented by Chemical Formula 1 of the present invention may be embodied in any one of Chemical Formulas 5 and 6 below depending on the bonding position of the amine-based moiety connected to the benzoxanthine-based moiety (eg, A).

[Formula 5]

[Formula 6]

In Formulas 5 and 6,

X, Ar ₁ , Ar ₂ , L and n are each as defined in claim 1.

For an embodiment of the present invention, the compounds represented by Chemical Formulas 5 and 6 may be more specific to any one of the following Chemical Formulas 7 to 12 according to the bonding position of the linker (L) bonded to the benzoxanthine-based moiety. . However, the present invention is not limited thereto.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formulas 7 to 12,

X, L and Ar ₁ and Ar ₂ are each as defined in claim 1.

The compound represented by Formula 1 of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by 1 to 300. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

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 linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

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

In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. In addition, 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, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include. Examples of 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 40 carbon atoms.

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 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" refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" refers to silyl substituted with aryl having 5 to 40 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.

<Organic electroluminescent device>

On the other hand, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') including the compound represented by the above-described formula (1).

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and 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 is and a compound represented by Formula 1 above. In this case, the compound may be used alone, or two or more may be used in combination.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a life improvement layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is the formula The compound represented by 1 is included. Specifically, the organic material layer including the compound represented by Formula 1 may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, a life improvement layer, a light emitting auxiliary layer, and an electron transport layer. More specifically, the organic material layer including the compound represented by Formula 1 may be at least one of a hole transport layer, a light emitting layer, and a hole injection layer.

According to an example, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the hole transport layer may include a compound represented by Formula 1 above. Optionally, a hole transport auxiliary layer may be further included between the hole transport layer and the light emitting layer.

In this case, the compound represented by Formula 1 may be used alone or mixed with a hole transport layer material known in the art as a hole transport layer material to be included in the organic electroluminescent device. The compound of Formula 1 has a high glass transition temperature, high hole mobility, and high hole transport ability, and due to the appropriate HOMO and LUMO energy levels between the hole injection layer and the light emitting layer, hole injection and transfer from the hole injection layer to the light emitting layer are smooth Do. Accordingly, the organic electroluminescent device including the compound of Formula 1 may have improved efficiency (luminous efficiency and power efficiency), lifespan, luminance, driving voltage, thermal stability, and the like.

The hole transport layer material compatible with the compound of Formula 1 is not particularly limited as long as it is a hole transport material commonly known in the art. For example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene-based derivatives; amine derivatives; TPD(N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N -carbazolyl) triphenylamine), etc.; NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis (4-methylphenyl)benzenamine]), but is not limited thereto, etc. These may be used alone or in combination of two or more.

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

According to another example, the at least one organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, wherein the emission layer includes a host and a dopant, and the host is represented by Formula 1 It may include the indicated compound. In this case, the light emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as the second host.

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

The compound represented by Formula 1 may be included in the organic electroluminescent device as a light emitting layer material, preferably green, blue and red phosphorescence, fluorescent host, or dopant. In this case, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency (luminous efficiency and power efficiency), lifespan, luminance, driving voltage, thermal stability, and the like of the organic electroluminescent device can be improved.

According to another example, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the electron transport layer may include a compound represented by Formula 1 . In this case, since the compound of Formula 1 has excellent electron transport ability, electrons can be easily moved from the electron transport layer to the light emitting layer. These compounds of Formula 1 may be used alone or may be mixed with electron transport layer materials 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 the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compounds, aluminum complexes (eg, Alq _3, tris(8-quinolinolato)-aluminium), and gallium complexes (eg, Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). 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, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and a cathode may be sequentially stacked. . At this time, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably the light emitting layer, the hole injection layer, the hole transport layer The compound represented by the above formula (1) may be included.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. there is.

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.

The substrate usable in the present invention is not particularly limited, and non-limiting examples include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, 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 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 multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

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

[Preparation Example 1] Synthesis of A-1

[1] Synthesis of methyl-8-(-3-bromophenyl)-1-naphthoate

(8-(methoxycarbonyl)naphthalen-1-yl)boronic acid 50.0g, 1-bromo-3-iodobenzene 55g, tetrakisphenylphosphinepalladium(0) 10.9g, K ₂ CO ₃ 50.1 g , THF 1L, water 250mL was added, and the mixture was stirred under reflux for 24 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with MC, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to methyl-8-(-3-bromine) Mophenyl)-1-naphthoate (51.2 g, yield 77%) was obtained.

[2] Synthesis of 10-bromo-7H-benzo [de] anthracen-7one

까지 냉각시킨 후 물을 첨가하여 석출된 고체를 여과한 뒤, MC에 녹여 황산마그네슘으로 건조시킨 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 10-브로모-7H-벤조[de]안트라센-7온 (34.0g, 수율 64%)을 얻었다.51.2 g of methyl-8-(-3-bromophenyl)-1-naphthoate was dissolved in 500 mL of methanesulfonic acid and stirred at room temperature. 0 when the reaction is complete

After cooling to , water was added and the precipitated solid was filtered, dissolved in MC, dried over magnesium sulfate, and then the resulting compound was purified by column chromatography to purify 10-bromo-7H-benzo [de] anthracen-7one (34.0 g, yield 64%) was obtained.

[3] Synthesis of 10-bromo-7- (2-phenoxyphenyl) -7H-benzo [de] anthracen-7-ol

로 냉각 교반시켰다. 그 후 2.5M n-부틸리튬을 30.5mL을 천천히 적가하였다. 30분 후 상기 10-브로모-7H-벤조[de]안트라센-7-온 21.5g을 무수 THF 100mL에 녹여 천천히 넣어준 후, 상온에서 3시간 교반하였다. 반응이 종료되면 물 250mL를 넣어 반응을 종료하고 MC 로 추출한 후 얻어진 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 생성물 10-브로모-7-(2-페녹시페닐)-7H-벤조[de]안트라센-7-올 (22.5g, 순도 72%)을 얻었다.Put 20 g of 1-bromo-2-phenoxybenzene and 250 mL of THF in a flask under nitrogen atmosphere and -78

was cooled and stirred. After that, 30.5 mL of 2.5M n-butyllithium was slowly added dropwise. After 30 minutes, 21.5 g of the 10-bromo-7H-benzo [de] anthracen-7-one was dissolved in 100 mL of anhydrous THF and slowly added thereto, followed by stirring at room temperature for 3 hours. When the reaction is complete, 250 mL of water is added to terminate the reaction, and the organic layer obtained after extraction with MC is dried over magnesium sulfate, concentrated, and the resulting compound is purified by column chromatography to obtain the product 10-bromo-7-(2-phenoxy). Phenyl)-7H-benzo [de] anthracen-7-ol (22.5 g, purity 72%) was obtained.

[4] Synthesis of A-1

Into a flask, 22.5 g of 10-bromo-7-(2-phenoxyphenyl)-7H-benzo [de] anthracen-7-ol, 200 mL of acetic acid, and 5.4 mL of HCl were added and stirred under reflux. After the reaction was completed, it was cooled to room temperature, 270 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 Compound A-1 (16.8 g, yield 74%).

1H-NMR: 8.50 (d, 1H), 8.03 (d, 2H), 7.91 (s, 1H), 7.74 (t, 1H), 7.44-7.14 (m, 9H), 7.01 (t, 2H), 6.86 ( d, 1H)

Mass : [(M+H) ⁺ ] : 463

[Preparation Example 2] Synthesis of A-2

에서 4시간 동안 가열 환류 하였다. 그 다음, 상기 가열 환류 하여 얻은 반응액의 온도를 상온으로 냉각하고, 상기 반응액에 염화암모늄 수용액 500mL를 투입하여 반응을 종결시킨 다음, EA 1.0 L로 추출하고, 증류수로 세척하여 유기층을 얻었다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압 증류한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 A-2 14.2g (수율 66%)을 얻었다.25.0 g of A-1 obtained in Preparation Example 1 and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-by (1,3,2-dioxabo) loran) was added to 16.5 g of 1,4-dioxane 500 mL. Then, after adding 2.3 g of Pd(dppf)Cl2 and 16.0 g of KOAc to the mixture, 130

It was heated and refluxed for 4 hours. Then, the temperature of the reaction solution obtained by heating and refluxing was cooled to room temperature, and 500 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water to obtain an organic layer. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and the resulting compound was purified by column chromatography to obtain 14.2 g of Compound A-2 (yield 66%).

1H-NMR: 8.50 (d, 1H), 8.03 (d, 2H), 7.91 (s, 1H), 7.74 (t, 1H), 7.44-7.14 (m, 9H), 7.01 (t, 2H), 6.86 ( d, 1H), 1.20 (s, 12H)

Mass : [(M+H) ⁺ ] : 510

[Preparation Example 3] Synthesis of A-3

[1] Synthesis of 7-(2-benzylphenyl)-10-bromo-7H-benzo[de]anthracen-7-ol

로 냉각 교반시켰다. 그 후 2.5M n-부틸리튬을 30.5mL을 천천히 적가하였다. 30분 후 상기 10-브로모-7H-벤조[de]안트라센-7-온 21.5g을 무수 THF 100mL에 녹여 천천히 넣어준 후, 상온에서 3시간 교반하였다. 반응이 종료되면 물 250mL를 넣어 반응을 종료하고 MC 로 추출한 후 얻어진 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 생성물 7-(2-벤질페닐)-10-브로모-7H-벤조[de]안트라센-7-올 (22.5g, 순도 72%)을 얻었다.In a flask under nitrogen atmosphere, 20 g of 1-bromo-2-phenoxybenzene synthesized in Preparation Example 1-2 and 250 mL of THF were added, and -78

was cooled and stirred. After that, 30.5 mL of 2.5M n-butyllithium was slowly added dropwise. After 30 minutes, 21.5 g of the 10-bromo-7H-benzo [de] anthracen-7-one was dissolved in 100 mL of anhydrous THF and slowly added thereto, followed by stirring at room temperature for 3 hours. When the reaction is complete, 250 mL of water is added to terminate the reaction, and the organic layer obtained after extraction with MC is dried over magnesium sulfate, concentrated, and the resulting compound is purified by column chromatography to obtain product 7-(2-benzylphenyl)-10-bro The parent-7H-benzo [de] anthracen-7-ol (22.5 g, purity 72%) was obtained.

[2] Synthesis of 10'-bromo-10H-spiro [anthracene-9,7'-benzo [de] anthracene]

22.5 g of 7-(2-benzylphenyl)-10-bromo-7H-benzo [de] anthracen-7-ol, 200 mL of acetic acid, and 5.4 mL of HCl were added to the flask and stirred under reflux. After the reaction was completed, it was cooled to room temperature, 270 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 10'-bromo-10H-spiro[anthracene-9,7'-benzo[ de]anthracene] (16.8 g, yield 74%) was obtained.

[3] Synthesis of A-3

에서 5분 동안 교반시키고 상온으로 올려서 iodomethane 40g을 첨가하였다. 반응이 완료되면 MC와 물로 추출한 후 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 A-3 (16.1g, 수율 90%)을 얻었다.In a round-bottom flask, 16.8 g of 10'-bromo-10H-spiro [anthracene-9,7'-benzo [de] anthracene] obtained in the above synthesis, 30 g of KOt-Bu, and 1 L of DMF were dissolved in 0

After stirring for 5 minutes at room temperature, 40 g of iodomethane was added. Upon completion of the reaction, the mixture was extracted with MC and water, the organic layer was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain Compound A-3 (16.1 g, yield 90%).

1H-NMR: 8.50 (d, 1H), 8.05 (d, 2H), 7.91 (d, 2H), 7.74 (t, 1H), 7,44-7.19 (m, 11H), 6.86 (d, 1H), 1.69 (s, 6H)

Mass : [(M+H) ⁺ ] : 489

[Preparation Example 4] Synthesis of A-4

에서 4시간 동안 가열 환류 하였다. 그 다음, 상기 가열 환류 하여 얻은 반응액의 온도를 상온으로 냉각하고, 상기 반응액에 염화암모늄 수용액 500mL를 투입하여 반응을 종결시킨 다음, EA 1.0 L로 추출하고, 증류수로 세척하여 유기층을 얻었다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압 증류한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 A-4 14.2g (수율 66%)을 얻었다.25.0 g of A-3 obtained in Preparation Example 3 and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-by (1,3,2-dioxabo) loran) was added to 16.5 g of 1,4-dioxane 500 mL. Then, after adding 2.3 g of Pd(dppf)Cl2 and 16.0 g of KOAc to the mixture, 130

It was heated and refluxed for 4 hours. Then, the temperature of the reaction solution obtained by heating and refluxing was cooled to room temperature, and 500 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water to obtain an organic layer. Thereafter, the obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and the resulting compound was purified by column chromatography to obtain 14.2 g of Compound A-4 (yield 66%).

1H-NMR: 8.50 (d, 1H), 8.05 (d, 2H), 7.91 (d, 2H), 7.74 (t, 1H), 7,44-7.19 (m, 11H), 6.86 (d, 1H), 1.69 (s, 6H), 1.20 (s, 12H)

Mass : [(M+H) ⁺ ] : 535

[Preparation Example 5] Synthesis of A-5

[1] Synthesis of 10-bromo-7- (2-phenoxyphenyl) -7H-benzo [de] anthracen-7-ol

로 냉각 교반시켰다. 그 후 2.5M n-부틸리튬을 30.5mL을 천천히 적가하였다. 30분 후 상기 10-브로모-7H-벤조[de]안트라센-7-온 21.5g을 무수 THF 100mL에 녹여 천천히 넣어준 후, 상온에서 3시간 교반하였다. 반응이 종료되면 물 250mL를 넣어 반응을 종료하고 MC 로 추출한 후 얻어진 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 생성물 10-브로모-7(2-(페닐싸이오)페닐)-7H-벤조[de]안트라센-7-올 (22.5g, 순도 72%)을 얻었다.In a flask under nitrogen atmosphere, 20 g of 1-bromo-2-phenoxybenzene synthesized in Preparation Example 1-2 and 250 mL of THF were added, and -78

was cooled and stirred. After that, 30.5 mL of 2.5M n-butyllithium was slowly added dropwise. After 30 minutes, 21.5 g of the 10-bromo-7H-benzo [de] anthracen-7-one was dissolved in 100 mL of anhydrous THF and slowly added thereto, followed by stirring at room temperature for 3 hours. Upon completion of the reaction, 250 mL of water was added to terminate the reaction, and the organic layer obtained after extraction with MC was dried over magnesium sulfate and concentrated, and the resulting compound was purified by column chromatography to obtain the product 10-bromo-7 (2-(phenylthio o)phenyl)-7H-benzo[de]anthracen-7-ol (22.5g, purity 72%) was obtained.

[2] Synthesis of A-5

22.5 g of 10-bromo-7(2-(phenylthio)phenyl)-7H-benzo[de]anthracen-7-ol, 200mL of acetic acid, and 5.4mL of HCl were added to the flask, and the mixture was stirred under reflux. After the reaction was completed, it was cooled to room temperature, 270 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 Compound A-5 (16.8 g, yield 74%).

1H-NMR: 8.50 (d, 1H), 8.05 (d, 2H), 7.91 (d, 1H), 7.74 (t, 1H), 7.69 (d, 2H), 7.44-7.30 (m, 5H), 7.05- 6.98 (m, 4H), 6.86 (d, 1H)

Mass : [(M+H) ⁺ ] : 479

[Preparation Example 6] Synthesis of A-6

에서 4시간 동안 가열 환류 하였다. 그 다음, 상기 가열 환류 하여 얻은 반응액의 온도를 상온으로 냉각하고, 상기 반응액에 염화암모늄 수용액 500mL를 투입하여 반응을 종결시킨 다음, EA 1.0 L로 추출하고, 증류수로 세척하여 유기층을 얻었다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압 증류한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 A-6 14.2g (수율 66%)을 얻었다.25.0 g of A-5 obtained in Preparation Example 5 and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-by (1,3,2-dioxabo) loran) was added to 16.5 g of 1,4-dioxane 500 mL. Then, after adding 2.3 g of Pd(dppf)Cl2 and 16.0 g of KOAc to the mixture, 130

It was heated and refluxed for 4 hours. Then, the temperature of the reaction solution obtained by heating and refluxing was cooled to room temperature, and 500 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water to obtain an organic layer. Then, the obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and the resulting compound was purified by column chromatography to obtain 14.2 g of Compound A-6 (yield 66%).

1H-NMR: 8.50 (d, 1H), 8.05 (d, 2H), 7.91 (d, 1H), 7.74 (t, 1H), 7.69 (d, 2H), 7.44-7.30 (m, 5H), 7.05- 6.98 (m, 4H), 6.86 (d, 1H), 1.20 (s, 12H)

Mass : [(M+H) ⁺ ] : 526

[Synthesis Example 1] Synthesis of compound 2

에서 3시간 동안 가열 환류하였다. 이후, 상기 가열 환류된 반응액의 온도를 상온으로 냉각한 다음, 이 반응액에 정제수 150mL를 투입하여 반응을 종결하였다. 반응 종결한 후 얻은 혼합액을 E.A 150mL로 추출한 후, 증류수로 세척하여 유기층을 얻었다. 얻어진 유기층을 황산 마그네슘으로 건조하고, 감압증류한 다음, 실리카겔 컬럼 크로마토그래피로 정제하여 화합물 2 (4.9g, 수율 72%)을 얻었다.After adding 100 mL of toluene to 5 g (1eq, 10.8 mmol) of A-1 obtained in Preparation Example 1 and 2.7 g (1eq, 10.8 mmol) of N-phenyl-[1,1'-biphenyl]-4-amine, this Pd ₂ (dba) ₃ 0.5g (0.05eq, 0.5 mmol), XPhos 0.5g (0.1eq, 1.1 mmol), NaOt-Bu 2.1g (2eq, 21.7 mmol) in the reaction solution, 120

It was heated and refluxed for 3 hours. Thereafter, the temperature of the heated and refluxed reaction solution was cooled to room temperature, and 150 mL of purified water was added to the reaction solution to terminate the reaction. After completion of the reaction, the obtained mixture was extracted with 150 mL of EA, and washed with distilled water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by silica gel column chromatography to obtain compound 2 (4.9 g, yield 72%).

Mass : [(M+H) ⁺ ] : 627

[Synthesis Example 2] Synthesis of compound 12

5g (leq, 9.8 mmol) of A-2 synthesized in Preparation Example 2 and 3.9g (leq, 9.8) of N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-3-amine mmol), tetrakisphenylphosphine palladium(0)[Pd(PPh ₃ ) ₄ ] 0.6 g (0.05eq, 0.5 mmol), and K ₂ CO ₃ 2.7 g (2eq, 19.7 mmol) in 100 ml of toluene, 25 ml of ethanol; It was put in 25ml of water and stirred 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 compound 12 (4.9 g, yield 71%).

Mass : [(M+H) ⁺ ] : 703

[Synthesis Example 3] Synthesis of compound 17

Compound 17 in the same manner as in Synthesis Example 1, except that N-phenyldibenzo[b,d]furan-3-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine (4.7 g, yield 69%) was prepared.

Mass : [(M+H) ⁺ ] : 640

[Synthesis Example 4] Synthesis of compound 27

N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-3-amine instead of N N-(4-bromophenyl)-N-phenyldibenzo[b,d]furan Compound 27 (4.6 g, yield 67%) was prepared in the same manner as in Synthesis Example 2, except that -3-amine was used.

Mass : [(M+H) ⁺ ] : 717

[Synthesis Example 5] Synthesis of compound 37

A compound in the same manner as in Synthesis Example 1, except that bis(dibenzo[b,d]furan-3-yl)amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine 37 (4.8 g, yield 68%) was prepared.

Mass : [(M+H) ⁺ ] : 731

[Synthesis Example 6] Synthesis of compound 47

N-(4-bromophenyl)-N-(dibenzo[b,d]furan- instead of N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-3-amine Compound 47 (4.6 g, yield 67%) was prepared in the same manner as in Synthesis Example 2, except that 3-yl) dibenzo [b, d] furan-2-amine was used.

Mass : [(M+H) ⁺ ] : 807

[Synthesis Example 7] Synthesis of compound 52

A compound in the same manner as in Synthesis Example 1, except that N-phenyldibenzo[b,d]thiophen-3-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine 52 (5.1 g, yield 73%) was prepared.

Mass : [(M+H) ⁺ ] : 657

[Synthesis Example 8] Synthesis of compound 62

N-(4-bromophenyl)-N-(dibenzo[b,d]furan- instead of N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-3-amine Compound 62 (4.8 g, yield 69%) was prepared in the same manner as in Synthesis Example 2, except that 3-yl) dibenzo [b, d] furan-2-amine was used.

Mass : [(M+H) ⁺ ] : 733

[Synthesis Example 9] Synthesis of compound 77

In the same manner as in Synthesis Example 1, except that N,9,9-triphenyl-9H-fluoren-2-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine Compound 77 (5.2 g, yield 71%) was prepared.

Mass : [(M+H) ⁺ ] : 791

[Synthesis Example 10] Synthesis of compound 92

N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine instead of N-phenyl-[1,1'-biphenyl]-4-amine Compound 92 (5.0 g, yield 69%) was prepared in the same manner as in Synthesis Example 1, except that it was used.

Mass : [(M+H) ⁺ ] : 757

[Synthesis Example 11] Synthesis of compound 102

Compound 102 (5.2 g, yield 70%) was prepared in the same manner as in Synthesis Example 1, except that A-3 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 653

[Synthesis Example 12] Synthesis of compound 112

Compound 112 (5.0 g, yield 68%) was prepared in the same manner as in Synthesis Example 2, except that A-4 was used instead of A-2.

Mass : [(M+H) ⁺ ] : 729

[Synthesis Example 13] Synthesis of compound 127

Compound 127 (4.8 g, yield 66%) was prepared in the same manner as in Synthesis Example 4, except that A-4 was used instead of A-2.

Mass : [(M+H) ⁺ ] : 743

[Synthesis Example 14] Synthesis of compound 152

Compound 152 (5.0 g, yield 68%) was prepared in the same manner as in Synthesis Example 7, except that A-3 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 683

[Synthesis Example 15] Synthesis of compound 177

Compound 177 (5.3 g, yield 67%) was prepared in the same manner as in Synthesis Example 9, except that A-3 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 818

[Synthesis Example 16] Synthesis of compound 192

Compound 192 (5.3 g, yield 69%) was prepared in the same manner as in Synthesis Example 10, except that A-3 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 784

[Synthesis Example 17] Synthesis of compound 202

Compound 202 (4.2 g, yield 63%) was prepared in the same manner as in Synthesis Example 1, except that A-5 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 643

[Synthesis Example 18] Synthesis of compound 212

Compound 212 (4.2 g, yield 61%) was prepared in the same manner as in Synthesis Example 2, except that A-6 was used instead of A-2.

Mass : [(M+H) ⁺ ] : 719

[Synthesis Example 19] Synthesis of compound 217

Compound 217 (4.0 g, yield 58%) was prepared in the same manner as in Synthesis Example 3, except that A-5 was used instead of A-1.

Mass : [(M+H) ⁺ ] : 657

[Synthesis Example 20] Synthesis of compound 262

Compound 112 (2.8 g, yield 41%) was prepared in the same manner as in Synthesis Example 8, except that A-6 was used instead of A-2.

Mass : [(M+H) ⁺ ] : 733

[Example 1] Fabrication of organic electroluminescent device

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a green organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500A was ultrasonically cleaned with distilled water. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE washer (Power sonic 405, Hwashin Tech), washed for 5 minutes using UV, and coated with a vacuum evaporator. The substrate was transferred.

m-MTDATA (60 nm)/(80 nm)/DS-H522 + 5% DS-501 (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/ An organic EL device was fabricated by stacking LiF (1 nm)/Al (200 nm) in the order. DS-H522 and DS-501 used at this time are products of Doosan Electronics BG, and the structures of m-MTDATA and BCP are as follows.

[Comparative Example 1] Fabrication of an organic electroluminescent device

An organic EL device was manufactured in the same manner as in Example 1, except that NPB was used as the hole transport layer material instead of Compound 2 used as the hole transport layer material when the hole transport layer was formed in Example 1. The structure of the used NPB is as follows.

[Evaluation Example 1]

For each of the green organic electroluminescent devices manufactured in Examples 1 to 20 and Comparative Example 1, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 1 compound 2 3.8 23.9 Example 2 compound 12 3.7 23.8 Example 3 compound 17 3.4 23.9 Example 4 compound 27 3.7 23.9 Example 5 compound 37 3.9 23.2 Example 6 compound 47 3.8 23.1 Example 7 compound 52 2.9 23.2 Example 8 compound 62 3.6 23.6 Example 9 compound 77 3.8 23.6 Example 10 compound 92 3.9 23.5 Example 11 compound 102 3.8 23.4 Example 12 compound 112 3.9 23.9 Example 13 compound 127 3.7 24.1 Example 14 compound 152 4.1 23.1 Example 15 compound 177 4.1 23.8 Example 16 compound 192 3.9 24.1 Example 17 compound 202 4.1 24.6 Example 18 compound 212 3.9 23.1 Example 19 compound 217 4.1 24.0 Example 20 compound 262 3.8 23.5 Comparative Example 1 NPB 4.8 20.5

As shown in Table 1, the organic electroluminescent devices of Examples 1 to 20 using the compound according to the present invention as a hole transport layer have current efficiency and It was found that the driving voltage exhibited excellent performance.

Claims (13)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X is C(R ₅ R ₆ ), O or S;
a to d are each independently an integer of 0 to 4,
R ₁ To R ₆ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C A 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,
However, at least one of R ₁ to R ₄ is represented by the following formula (2),
[Formula 2]

In Formula 2,
* is the part where the bond is made,
n is an integer from 0 to 3,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a C 3 to C 18 heteroarylene group,
Ar ₁ and Ar ₂ are the same as or different from each other, and 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, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , 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 An aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,
Arylene group of L, heteroarylene group, Ar ₁ To Ar ₂ And R ₁ To R ₆ Of the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, arylox Group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine 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 ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₁ to C ₄₀ Alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ 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 Arylamine It is substituted or unsubstituted with one or more substituents selected from the group consisting of a group, and in this case, when a plurality of the substituents are the same or different from each other.
According to claim 1,
Wherein Ar ₁ And Ar ₂ Are the same as or different from each other, and each independently C ₆ ~ C ₆₀ A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
According to claim 1,
Wherein Ar ₁ And Ar ₂ Are the same as or different from each other, and each independently a compound represented by any one of the following Chemical Formulas 3 and 4:
[Formula 3]

[Formula 4]

In Formula 3 or 4,
* means a portion where a bond is formed with Chemical Formula 2,
Z is (CR ₇ R ₈ ) or O,
m is an integer from 1 to 3,
R, R ₇ and R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ 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,
These may combine to form a condensed ring.
According to claim 1,
Wherein Ar ₁ And Ar ₂ Are the same as or different from each other, and each independently a compound selected from the following structural formula:

In the above formula,
* denotes a portion in which a bond with Chemical Formula 2 is formed.
According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 5 and 6 below:
[Formula 5]

[Formula 6]

In Formulas 5 and 6,
X, Ar ₁ , Ar ₂ , L and n are each as defined in claim 1.
According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 7 to 12:
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formulas 7 to 12,
X, L and Ar ₁ and Ar ₂ are each as defined in claim 1.
According to claim 1,
wherein L is a single bond or a linker selected from the following structural formulae.

In the above formula,
* denotes a portion at which a bond with Chemical Formula 1 is formed.
According to claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of the following compounds:

According to claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of the following compounds:

According to claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of the following compounds:

According to claim 1,
The compound represented by Formula 1 is a material of a hole transport layer or a hole injection layer.
(i) an anode, (ii) a cathode, and (iii) a single layer interposed between the anode and the cathode
As an organic electroluminescent device comprising the above organic material layer,
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 11.
13. The method of claim 12,
The organic material layer containing the compound is an organic electroluminescent device that is a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer or a life improvement layer.