KR20230095190A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound having excellent hole and electron injection and transport capabilities, luminescent performance, and the like, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the organic compound in one or more organic material layers.

Description

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

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

Research on organic electroluminescent devices, which led to blue electroluminescence using an anthracene single crystal in 1965 from Bernanose's observation of organic thin film emission in the 1950s, was divided into a hole layer and a functional layer of light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure is presented. 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 specialized materials used therein.

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

Materials for the light emitting layer of the organic electroluminescent device may be classified into blue, green, and red light emitting materials according to the light emitting color. In addition, yellow and orange light emitting materials are also used as light emitting materials for implementing better natural colors. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material may be divided into a phosphorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants. Until now, NPB, BCP, Alq ₃ , etc. are widely known as materials used in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials. . In particular, phosphorescent materials that have a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) ₂ and the like as blue, green, and red dopant materials. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.

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

An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and has excellent hole and electron injection and transport capabilities, luminescent performance, and the like.

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

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

In Formula 1,

A plurality of X's are the same as or different from each other, and are each independently C(R ₁ ) or N, provided that at least one of the plurality of X's is N,

When R ₁ is plural, the plural R _1s are the same as or different from each other, and are each independently selected from hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, and C ₂ to 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, 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 ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group, C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, a C ₅ ~ C ₆₀ arylheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms;

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a C ₁ ~ C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, a C ₂ ~ C ₄₀ alkynyl group, a C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phospha Nyl group, C ₆ ~ C ₆₀ monoarylphosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ arylheteroarylamine group and nuclear atom It is selected from the group consisting of 5 to 60 heteroarylamine groups, or they may combine with adjacent groups to form a condensed ring;

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

n and p are each an integer from 0 to 2,

an arylene group or a heteroarylene group of L; An _alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron of Ar 1 to Ar ₂ , and R ₁ Group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, heavy hydrogen (D), 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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, hetero having 5 to 60 nuclear atoms Aryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same as or different from each other.

In addition, the present invention is an organic electroluminescent device including an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound represented by Formula 1. provides

Here, the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a light emitting layer, an auxiliary light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer. there is. In this case, the compound represented by Formula 1 may be included as at least one material of the phosphorescent host material of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer.

For example, the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic electroluminescent device because it has excellent electron transport ability, luminescent ability, heat resistance, and the like.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host, electron transport layer or electron transport auxiliary layer material, it has high thermal stability, low driving voltage, fast mobility, and high current efficiency compared to conventional host materials or electron transport materials. and long life characteristics.

Accordingly, aspects such as excellent light emitting performance, low driving voltage, long lifespan, and high efficiency of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and thus can be effectively applied to a full color display panel or the like.

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

Hereinafter, the present invention will be described in detail.

<New organic compounds>

In the present invention, it is intended to provide a novel aryl-based compound having excellent thermal stability, carrier transport ability, and luminescent ability, and a novel electroluminescent material that can simultaneously realize characteristics of a device, such as low voltage, high efficiency, and long lifespan.

Specifically, the novel compound represented by Formula 1 of the present invention adopts a terphenyl group as a core, and at least one electron withdrawing group (EWG) having excellent electron transport ability is bonded to the core structure. It forms the basic skeletal structure.

The compound represented by Formula 1, as the terphenyl group is substituted in the core, structurally increases steric hindrance, thereby increasing efficiency compared to conventionally known material structures, and in terms of glass transition temperature (Tg) and thermal stability. better than In addition, by introducing an azine group (e.g., nitrogen-containing heteroaromatic ring), which is a functional group with strong electron withdrawing ability (EWG), to improve the electron transfer rate, it is possible to have more suitable physicochemical properties for electron injection and electron transport. .

In addition, since the compound represented by Chemical Formula 1 of the present invention has high triplet energy, it is possible to prevent excitons generated in the light emitting layer from diffusing (moving) to an adjacent electron transport layer or hole transport layer. Accordingly, the number of excitons contributing to light emission in the light emitting layer is increased so that the light emitting efficiency of the device can be improved, and the lifespan of the device can be effectively increased by improving durability and stability of the device. Most of the developed materials are capable of low-voltage driving, thereby exhibiting physical characteristics that improve lifespan.

As described above, the compound represented by Formula 1 of the present invention is used as an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), an electron transport layer/injection layer material, and a hole hole material. When applied as a transport layer/injection layer material, a light emitting auxiliary layer material, and a lifespan improvement layer material, the performance and lifespan characteristics of the organic EL device can be greatly improved. As a result, such an organic light emitting device can maximize the performance of a full-color organic light emitting panel.

On the other hand, the red and green light emitting layers of the organic electroluminescent device use phosphorescent materials, respectively, and their technological maturity is currently high. In contrast, the blue light emitting layer includes a fluorescent material and a phosphorescent material, of which the fluorescent material needs to improve its performance, and the blue phosphorescent material is still under development and thus has a high entry barrier. That is, since the blue light emitting layer has a high development potential but a relatively high technical difficulty, there is a limit to improving performance (eg, driving voltage, efficiency, lifespan, etc.) of a blue organic light emitting device including the blue light emitting layer. Accordingly, in the present invention, the compound of Chemical Formula 1 may be applied as a material for an electron transport layer (ETL) or an electron transport auxiliary layer in addition to the light emitting layer (EML). In this way, the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic electroluminescent device having the same can be improved through a material change of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic electroluminescent device. There is an advantage to being able to

According to the present invention, the compound represented by Formula 1 includes a terphenyl group as a core, and the core structure contains an electron withdrawing group (EWG) having excellent electron transport ability, such as a nitrogen-containing heterocyclic ring (X-containing rings) are bonded, but they form a basic skeleton structure in which they are directly linked or linked through a separate linker (L).

The nitrogen-containing heterocycle (eg, X-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom. For one embodiment of the nitrogen-containing heteroaromatic ring (eg, ring containing X), a plurality of X's are the same as or different from each other, and each independently represents N or CR ₁ , provided that at least one of the plurality of X's is N. For a specific example, the plurality of X's includes 2 to 3 N's, and preferably includes 3 N's. In this way, by including a heterocyclic ring containing 2 to 3 nitrogens, more excellent electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

In addition, the nitrogen-containing heterocycle (eg, X-containing ring) may be a polycyclic condensed ring formed by combining adjacent groups (eg, Ar ₁ to Ar ₂ ).

For one specific example, the nitrogen-containing heterocycle (X-containing ring) may be any one selected from the following structural formulas. However, it is not limited thereto.

In the above formula,

* means a site connected to Formula 1,

Z is O or S;

Here, Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 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 alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C It is selected from the group consisting of a ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, or by combining them with an adjacent group (eg, an X-containing ring-azine group) Can form condensed rings. Specifically, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently may be selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and more specifically It is preferable that they are each independently a C ₆ ~ C ₁₈ aryl group and a heteroaryl group having 5 to 18 nuclear atoms.

A specific example of Ar ₁ and Ar ₂ may be represented by the following structural formula.

In the above formula,

* means a site connected to Formula 1 above.

R ₁ located in the nitrogen-containing heterocycle (eg, ring containing X) is 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, 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ It may be selected from the group consisting of a ~C ₆₀ arylboron group, a C ₁ ~C ₄₀ phosphine group, a C ₁ ~C ₄₀ phosphine oxide group, and a C ₆ ~C ₆₀ arylamine group. Specifically, R ₁ is preferably selected from the group consisting of hydrogen, heavy hydrogen, a cyano group, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

The nitrogen-containing heterocycle (eg, X-containing ring) according to the present invention is connected to the terphenyl-based core through a direct bond or a separate linker (eg, L).

The terphenyl-based core is superior in terms of glass transition temperature (Tg) and thermal stability by structurally increasing steric hindrance. In particular, at least one aryl group (eg, phenyl group, etc.) at a specific position, for example, 1, 3, 4, 5 position, compared to a conventional terphenyl structure compound (eg, aryl group disposed at 1,2,3,5-position) By being arranged, triplet (T1) energy is increased by steric hinderance and efficiency can be increased by increasing electron mobility due to a weak donor effect. The terphenyl-based core is not particularly limited as long as it includes a terphenyl group moiety, and examples thereof include ortho-terphenyl, meta-terphenyl, and para-terphenyl. Specifically, the core includes a para-terphenyl group, and may have a structure in which at least two identical or different aryl groups are connected symmetrically or asymmetrically around the terphenyl group. For example, a phenyl group may be disposed on one side or one side and the other side centered on a terphenyl group. For example, a phenyl group (n = 0), a biphenyl group (n = 1), or a terphenyl group (n = 2) may be connected to one side of the terphenyl group, and a single bond (p = 0), a phenyl group (p = 1), a biphenyl group (p=2) may be connected.

The aforementioned terphenyl-based core and the nitrogen-containing aromatic ring (eg, X-containing ring) are bonded directly or through a linker (L). As such, when a separate linker exists between the above-mentioned moiety and the nitrogen-containing aromatic ring, the HOMO region can be expanded to give a benefit to the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO. .

The linker (eg, L) is not particularly limited, and may be a single bond or a conventional divalent group linker known in the art. For example, L is the same as or different from each other, and each independently a single bond (eg, direct bond) or C ₆ ~ C ₁₈ It is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. can Specifically, it has an arylene group moiety of Formula 2 below or a dibenzo-based moiety of Formula 3 below.

[Formula 2]

[Formula 3]

In Formula 2 or 3,

* denotes a portion bonded to Formula 1,

Y is selected from the group consisting of O, S and Se,

m is an integer from 1 to 3;

The moiety of Formula 2 may be an arylene linker known in the art, and specific examples thereof include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, and a carbazolyl group. A rene group, a thiophenylene group, an indolylene group, a purinylene group, a quinolinylene group, a pyrrolene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a pyridinylene group, a pyrimidinylene group, and the like. More specifically, the linker (L) represented by Formula 2 is preferably a phenylene group or a biphenylene group.

For one embodiment of the present invention, the linker (L) of Formula 2 may be a linker selected from the following structural formulas.

In addition, the linker of Chemical Formula 3 may be a dibenzo-based moiety known in the art. For example, it has a dibenzofuran-based (Y = O) moiety, a dibenzothiophene-based (Y = S) moiety, and/or a dibenzoselenophenone-based (Y = Se) moiety.

The dibenzo-based moiety represented by Chemical Formula 3 may be more specifically represented by the following structural formula.

In the above formula,

* means a part where the bond with Formula 1 is made. In addition, although the linker (L) of Formulas 2 and/or 3 described above is not shown in the formula, at least one substituent (eg, R ₁ ) known in the art may be substituted.

In the above formula (1), the L of the arylene group, heteroarylene group; An _alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron of Ar 1 to Ar ₂ , and R ₁ Group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, heavy hydrogen (D), 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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, hetero having 5 to 60 nuclear atoms Aryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same as or different from each other.

According to an embodiment of the present invention, the compound represented by Chemical Formula 1 may be further embodied by any one of the following Chemical Formulas 4 to 7 according to the type of the linker (L) and Ar ₁ to Ar ₂ . However, it is not limited thereto.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In the above formula,

X, Y, Ar ₁ , Ar ₂ , m, n and p are each as defined in Formula 1.

For another embodiment of the present invention, the compound represented by Formula 1 may be further embodied by any one of the following Formulas 8 to 13 according to the type of polycyclic condensed ring formed by combining an X-containing ring, which is an EWG group, with an adjacent group. However, it is not limited thereto.

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In the above formula,

L, Z, Ar ₂ , n and p are each as defined in Formula 1.

In another embodiment of the present invention, the compound represented by Formula 1 is one of the following Formulas 14 to 17 depending on the bonding position of the aromatic ring (eg, the first aryl group) bonded to one side of the terphenyl-based core. can be displayed However, it is not limited thereto.

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Formulas 14 to 17,

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

For another embodiment of the present invention, the compound represented by Chemical Formula 1 is represented by the following Chemical Formulas 18 to 10 according to the number (eg, p) of aromatic rings (eg, second aryl groups) bonded to the other side of the terphenyl-based core. It can be displayed as any one of 20. However, it is not limited thereto.

[Formula 18]

[Formula 19]

[Formula 20]

In Chemical Formulas 18 to 20,

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

The compound represented by Formula 1 of the present invention described above may be further exemplified by compounds represented by 1 to 592, such as the compounds exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

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

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

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

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

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.

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

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. can include Examples of 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" means 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 one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or a heteroatom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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.

<Electron transport layer material>

The present invention provides an electron transport layer comprising the compound represented by Formula 1 above.

The electron transport layer (ETL) serves to move electrons injected from the cathode to an adjacent layer, specifically the light emitting layer.

The compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with electron transport layer materials known in the art. It is preferably used alone.

Materials for the electron transport layer that can be mixed with the compound of Formula 1 include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene ( perylene)-based compounds, aluminum complexes (e.g. Alq ₃ (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq '2OAc, 2(Gaq'2)), 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 electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and may be appropriately adjusted within a range known in the art.

<Electron Transport Auxiliary Layer Material>

In addition, the present invention provides an electron transport auxiliary layer comprising the compound represented by Formula 1 above.

The electron transport layer is disposed between the light emitting layer and the electron transport layer, and serves to prevent diffusion of excitons or holes generated in the light emitting layer to the electron transport layer.

The compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with electron transport layer materials known in the art. It is preferably used alone.

The electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a nitrogen-containing heterocyclic derivative, and the like.

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

<Organic electroluminescent device>

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) including the compound represented by Formula 1 according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising 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 It includes the compound represented by Formula 1 above. In this case, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer among them may be one or more of the above chemical formula. It includes the compound represented by 1. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer (more specifically, a phosphorescent host material), an electron transport layer, and an electron transport auxiliary layer.

The light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material. In this case, the compound of Formula 1 may be included as the host material. In addition, the light emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

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

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are 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 a light emitting layer, more preferably a phosphorescent host. may include the compound represented by Formula 1 above. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

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 may 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 among the organic material layers includes the compound represented by Chemical Formula 1. there is.

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

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

In addition, as the cathode material, any cathode material known in the art may be used without limitation. For example, 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, as the negative electrode material, negative electrode materials known in the art may be used without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multi-layered materials such as LiF/Al or LiO2/Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.

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

[Preparation example]

[Preparation Example 1]

<Step 1> Synthesis of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl

2'-bromo-6'-chloro-1,1':4',1''-terphenyl 50g (145.5mmol) and phenylboronic acid 21.3g (174.6mmol), Pd(PPh3)4 5.04g (4.36mmol), 60.3g (436.5.4mmol) of K2CO3 was added to 400ml of Toluene, 100ml of EtOH, and 100ml of H2O, followed by heating under reflux for 3 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl (40.2 g, yield 81%).

Mass : [(M+H) ⁺ ] : 341

<Step 2> Synthesis of Core1

3'-chloro-5'-phenyl-1,1':2',1''-terphenyl (40.2g, 117.9 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (36 g, 141.5 mmol) and Pd(dppf)Cl ₂ (2.59 g, 3.54 mmol), KOAc (34.7 g, 353.8 mmol), Xphos (5.62 g, 11.79 mmol) was added to 750 ml of 1,4-Dioxane and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, Core1 (34.6 g, yield 68%) was obtained by column chromatography.

[LCMS]: 433

[Preparation Example 2] Synthesis of Core 2

[Preparation Example 1] Except for using [1,1'-biphenyl]-2-ylboronic acid as the reactant in <Step 1>, the same process as in [Preparation Example 1] was performed to obtain 38.7 g of Core2 (yield: 68%). got

[LCMS]: 509

[Preparation Example 3] Synthesis of Core 3

[Preparation Example 1] Except for using [1,1'-biphenyl]-3-ylboronic acid as the reactant in <Step 1>, the same process as in [Preparation Example 1] was performed to obtain 40.4 g of Core3 (71% yield). got

[LCMS]: 509

[Preparation Example 4] Synthesis of Core 4

[Preparation Example 1] Except for using [1,1'-biphenyl]-4-ylboronic acid as the reactant in <Step 1>, the same process as in [Preparation Example 1] was performed to obtain 39.4 g of Core4 (yield: 69%). got

[LCMS]: 509

[Synthesis Example]

[Synthesis Example 1] Synthesis of Compound Inv 3

[Preparation Example 1] Core1 (10 g, 23.1 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (8.1 g, 19.3 mmol) and Pd (OAc) ₂ ( 0.13 g, 0.57 mmol), Cs ₂ CO ₃ (12.5 g, 38.5 mmol), and Xphos (0.92 g, 1.92 mmol) were added to 100 ml of Toluene, 25 ml of EtOH, and 25 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent from the filtered organic layer, Inv 3 (8.8 g, yield 66%) was obtained by column chromatography.

[LCMS]: 690

[Synthesis Example 2] Synthesis of Compound Inv 23

4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1, Inv 23 (9.3 g, yield 63%) was obtained in the same manner as in [Synthesis Example 1] except that 1'-biphenyl] -4-yl) -2-phenylpyrimidine (9.54 g 19.27 mmol) was used.

[LCMS]: 765

[Synthesis Example 3] Synthesis of Compound Inv 38

2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using 1,3,5-triazine (8.36g 19.2mmol), Inv 38 (8.9 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 704

[Synthesis Example 4] Synthesis of compound Inv 61

2-(6-(3-chlorophenyl)dibenzo[b,d]furan-2-yl)-4,6-diphenyl instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using -1,3,5-triazine (9.82g 19.2mmol), Inv 61 (9.5 g, yield 63%) was obtained in the same manner as [Synthesis Example 1].

[LCMS] : 780

[Synthesis Example 5] Synthesis of Compound Inv 78

2-(3-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using phenyl-1,3,5-triazine (9.32g 19.2mmol), Inv 78 (9.3 g, yield 64%) was obtained in the same manner as in [Synthesis Example 1].

[LCMS]: 754

[Synthesis Example 6] Synthesis of Compound Inv 97

4-(3-chlorophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (7.18g) instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Inv 97 (8.4 g, yield 68%) was obtained by performing the same procedure as [Synthesis Example 1] except that 19.2 mmol) was used.

[LCMS]: 643

[Synthesis Example 7] Synthesis of Compound Inv 134

4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Inv 134 (8.6 g, yield 65%) was obtained by performing the same procedure as [Synthesis Example 1] except that (8.07 g 19.2 mmol) was used.

[LCMS]: 689

[Synthesis Example 8] Synthesis of Compound Inv 155

2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b Inv 155 (9.2 g, Yield 61%) was obtained.

[LCMS] : 780

[Synthesis Example 9] Synthesis of Compound Inv 184

2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using 1,3,5-triazine (8.67g 19.2mmol), Inv 184 (9.0 g, yield 65%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 720

[Synthesis Example 10] Synthesis of Compound Inv 190

2-(4-chlorophenyl)-4-(naphtho[2,3-b]benzofuran-2-yl)-6- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using phenyl-1,3,5-triazine (9.32g 19.2mmol), Inv 190 (9.6 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 754

[Synthesis Example 11] Synthesis of Compound Inv 205

2-(benzo[kl]xanthen-8-yl)-4-(4-chlorophenyl)-6-phenyl-1 instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine; Except for using 3,5-triazine (9.32g 19.2mmol), Inv 205 (9.1 g, yield 63%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 754

[Synthesis Example 12] Synthesis of Compound Inv 217

2-(4-chlorophenyl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl) instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Except for using -6-phenyl-1,3,5-triazine (9.83g 19.2mmol), Inv 217 (9.5 g, yield 63%) was obtained in the same manner as in [Synthesis Example 1].

[LCMS] : 780

[Synthesis Example 13] Synthesis of Compound Inv 239

Core2 (10 g, 19.66 mmol) was used instead of Core1, and 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (5.61 g) was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Inv 239 (7.6 g, yield 67%) was obtained by performing the same procedure as [Synthesis Example 1] except that 16.39 mmol) was used.

[LCMS]: 689

[Synthesis Example 14] Synthesis of Compound Inv 257

2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine ( Inv 257 (8.1 g, yield 63%) was obtained by performing the same procedure as [Synthesis Example 13] except that 7.11g 16.3mmol) was used.

[LCMS] : 780

[Synthesis Example 15] Synthesis of Compound Inv 283

2-(6-(3-chlorophenyl)dibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine Inv 283 (8.9 g, yield 63%) was obtained by performing the same procedure as [Synthesis Example 13] except that (8.35 g 16.3 mmol) was used.

[LCMS]: 857

[Synthesis Example 16] Synthesis of Compound Inv 315

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4-(naphtho[2,1-b]benzofuran-9 instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine Inv 315 (9.5 g, yield 64%) was obtained by performing the same procedure as in [Synthesis Example 13] except that -yl) -6-phenyl-1,3,5-triazine (9.17g 16.3mmol) was used. .

[LCMS]: 907

[Synthesis Example 17] Synthesis of Compound Inv 331

2-(3-chlorophenyl)-4-(3-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenyl-1,3 instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine Except for using ,5-triazine (8.35 g, 16.3 mmol), Inv 331 (9.3 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 13].

[LCMS]: 857

[Synthesis Example 18] Synthesis of Compound Inv 336

2-(3-chlorophenyl)-4-phenyl-6-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,5- instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine Inv 336 (9.2 g, yield 65%) was obtained by performing the same procedure as [Synthesis Example 13] except that triazine (8.35 g 16.3 mmol) was used.

[LCMS]: 857

[Synthesis Example 19] Synthesis of Compound Inv 348

Core3 (10 g, 19.66 mmol) was used instead of Core1 and 2-([1,1'-biphenyl]-4-yl) instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Inv 348 (8.5 g, yield 68%) was obtained.

[LCMS]: 766

[Synthesis Example 20] Synthesis of Compound Inv 376

2-(3'-chloro-[1,1') instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine Except for using -biphenyl]-4-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (8.35g 16.3mmol) [synthesis Example 19] to obtain Inv 376 (9.2 g, yield 65%).

[LCMS]: 857

[Synthesis Example 21] Synthesis of Compound Inv 412

2-(3-chlorophenyl)-4-(naphtho[ Inv 412 (Inv 412 ( 9.0 g, yield 66%) was obtained.

[LCMS]: 830

[Synthesis Example 22] Synthesis of Compound Inv 428

2-(3'-chloro-[1,1') instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine Except for using -biphenyl]-4-yl)-4-(naphtho[2,1-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine (9.17.0g 16.3mmol) was obtained by performing the same process as in [Synthesis Example 19] to obtain Inv 428 (9.1 g, yield 61%).

[LCMS]: 907

[Synthesis Example 23] Synthesis of Compound Inv 437

2-(3-chlorophenyl)-4-phenylbenzo[4 instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine Inv 437 (7.8 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 19] except that ,5]thieno[3,2-d]pyrimidine (6.11g 16.3mmol) was used.

[LCMS]: 719

[Synthesis Example 24] Synthesis of Compound Inv 449

2-(3-chlorophenyl)-4-(dibenzo[ b, d] furan-3-yl) -6- (naphthalen-2-yl) -1,3,5-triazine (7.93.0g 16.3mmol) except for using the same procedure as [Synthesis Example 19] This was carried out to obtain Inv 449 (8.8 g, yield 65%).

[LCMS]: 830

[Synthesis Example 25] Synthesis of Compound Inv 473

Core4 (10 g, 19.66 mmol) was used instead of Core1, and 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (5.61 g) was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Inv 473 (7.7 g, yield 68%) was obtained by performing the same procedure as [Synthesis Example 1] except that 16.3 mmol) was used.

[LCMS]: 689

[Synthesis Example 26] Synthesis of Compound Inv 495

2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-bis(dibenzo[b,d]furan- 3-yl) -1,3,5-triazine (9.83g 16.3mmol) except for using [Synthesis Example 25] to obtain Inv 495 (9.5 g, yield 61%) in the same manner as in [Synthesis Example 25].

[LCMS]: 947

[Synthesis Example 27] Synthesis of Compound Inv 508

2-(6-(4-chlorophenyl)dibenzo[b,d]thiophen-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine Inv 508 (8.9 g, yield 62%) was obtained by performing the same procedure as [Synthesis Example 25] except that (8.62 g 16.3 mmol) was used.

[LCMS]: 873

[Synthesis Example 28] Synthesis of Compound Inv 544

2-(benzo[kl]xanthen-9-yl)-4-(4'-chloro-[1,1'-biphenyl]-3-yl)- instead of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine Except for using 6-phenyl-1,3,5-triazine (9.17g 16.3mmol), Inv 544 (9.2 g, yield 62%) was obtained by performing the same procedure as in [Synthesis Example 25].

[LCMS]: 907

[Synthesis Example 29] Synthesis of Compound Inv 559

2-(4-chlorophenyl)-4-phenyl-6-(7-phenyldibenzo[b,d]furan-3-yl)-1,3,5- instead of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine Inv 559 (9.3 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 25] except that triazine (8.35 g 16.3 mmol) was used.

[LCMS]: 857

[Synthesis Example 30] Synthesis of Compound Inv 564

2-(4-chlorophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (6.45g 16.3mmol) instead of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine Inv 564 (7.9 g, yield 65%) was obtained by performing the same procedure as in [Synthesis Example 25] except for the use.

[LCMS]: 740

[Synthesis Example 31] Synthesis of Compound Inv 568

Instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3, Except for using 5-triazine (6.89g 19.2mmol), Inv 568 (8.0 g, yield 66%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 628

[Synthesis Example 32] Synthesis of Compound Inv 571

2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.86g 16.3mmol) instead of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine ) Inv 571 (7.7 g, yield 67%) was obtained by performing the same procedure as [Synthesis Example 13] except for using.

[LCMS]: 704

[Synthesis Example 33] Synthesis of Compound Inv 574

2-chloro-4-(dibenzo[b,d] instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine furan-2-yl) -6-phenyl-1,3,5-triazine (5.86g 16.3mmol) was carried out in the same manner as [Synthesis Example 19], except for using Inv 574 (7.5 g, yield 65%) ) was obtained.

[LCMS]: 704

[Synthesis Example 34] Synthesis of Compound Inv 579

2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.86g 16.3mmol) instead of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine ) Inv 579 (7.3 g, yield 63%) was obtained by performing the same procedure as [Synthesis Example 25] except for using.

[LCMS]: 704

[Synthesis Example 35] Synthesis of Compound Inv 581

2-chloro-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1 instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine; Except for using 3,5-triazine (7.86g 19.2mmol), Inv 581 (8.1 g, yield 62%) was obtained by performing the same procedure as [Synthesis Example 1].

[LCMS]: 678

[Examples 1 to 10] Fabrication of blue organic electroluminescent device

Compounds Inv 3 to Inv 581 were subjected to high-purity sublimation purification by a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

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

On the ITO transparent electrode prepared as above, DS-205 (Solus Advanced Materials, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Solus Advanced Materials, 30 nm)/ Inv 3 ~ Inv Each compound of 581 (30 nm)/LiF (1 nm)/Al (200 nm) was laminated in this order to prepare an organic electroluminescent device.

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

[Comparative Example 1] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq3 was deposited at 30 nm instead of Inv 3 as an electron transport layer material.

[Evaluation Example 1]

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

Sample electron transport layer driving voltage
(V) current efficiency
(cd/A) EL peak
(nm) Example 1 Inv 3 4.0 7.0 458 Example 2 Inv 97 4.1 7.0 459 Example 3 Inv 336 3.8 6.9 459 Example 4 Inv 449 3.9 7.0 459 Example 5 Inv 559 3.8 7.1 459 Example 6 Inv 568 3.7 7.1 458 Example 7 Inv 571 4.2 7.1 459 Example 8 Inv 574 3.8 7.2 459 Example 9 Inv 579 3.9 7.0 458 Example 10 Inv 581 4.1 6.9 459 Comparative Example 1 Alq3 4.8 5.8 460

As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 10 using the compound of the present invention for the electron transport layer are compared to the blue organic electroluminescent device of Comparative Example 1 using Alq3 as the electron transport layer material. It was found that excellent performance was exhibited in terms of driving voltage, emission peak and current efficiency.

[Examples 11 to 45] Preparation of blue organic electroluminescent device

Compounds Inv 3 to Inv 581 were subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.

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

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Solus Advanced Materials, 30 nm) / Inv 3 ~ Inv 581 of each compound ( 30 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare an organic electroluminescent device.

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

[Comparative Example 2] Preparation of blue organic electroluminescent device

Except for not using Inv 3 used as the electron transport auxiliary layer material in Example 11 and depositing the electron transport layer material Alq ₃ at 30 nm instead of 25 nm, the same procedure as in Example 11 was carried out to produce a blue organic material. An electroluminescent device was fabricated.

[Comparative Examples 3 to 4] Fabrication of blue organic electroluminescent device

Blue organic electroluminescent devices of Comparative Examples 3 to 4 were manufactured in the same manner as in Example 11, except that Compound A and Compound B were respectively used instead of Inv 3 as the electron transport auxiliary layer material.

The structures of Compound A and Compound B used in Comparative Examples 3 to 4 are as follows, respectively.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 11 to 45 and Comparative Examples 2 to 4, driving voltage, emission wavelength, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm 2 , and the results are shown in the table below. 2.

Sample electronic transportation
auxiliary layer driving voltage
(V) current efficiency
(cd/A) EL peak
(nm) Example 11 Inv 3 4.0 7.4 457 Example 12 Inv 23 3.8 7.6 458 Example 13 Inv 38 3.9 7.8 458 Example 14 Inv 61 3.9 7.6 457 Example 15 Inv 78 4.0 7.6 458 Example 16 Inv 97 4.1 7.5 458 Example 17 Inv 134 3.8 7.6 458 Example 18 Inv 156 3.7 7.3 458 Example 19 Inv 184 4.2 7.4 458 Example 20 Inv 190 4.1 7.2 457 Example 21 Inv 205 4.2 7.6 458 Example 22 Inv 217 3.9 7.2 458 Example 23 Inv 239 4.2 7.5 457 Example 24 Inv 257 4.2 7.2 458 Example 25 Inv 283 4.0 7.2 458 Example 26 Inv 315 3.7 7.4 458 Example 27 Inv 331 4.1 7.6 458 Example 28 Inv 336 4.3 7.6 458 Example 29 Inv 348 3.9 7.4 457 Example 30 Inv 376 4.2 7.8 458 Example 31 Inv 412 4.1 7.2 458 Example 32 Inv 428 3.8 7.8 457 Example 33 Inv 437 4.0 7.5 458 Example 34 Inv 449 3.9 7.5 458 Example 35 Inv 473 3.6 8.0 458 Example 36 Inv 495 3.6 7.4 457 Example 37 Inv 508 4.2 7.6 458 Example 38 Inv 544 3.6 8.2 458 Example 39 Inv 559 3.9 7.8 458 Example 40 Inv 564 3.6 7.8 457 Example 41 Inv 568 4.2 7.4 458 Example 42 Inv 571 3.6 7.8 458 Example 43 Inv 574 3.7 7.8 457 Example 44 Inv 579 3.9 7.4 458 Example 45 Inv 581 3.9 7.4 458 Comparative Example 2 - 4.7 5.6 457 Comparative Example 3 A 4.5 6.8 456 Comparative Example 4 B 4.4 6.5 457

As shown in Table 2, the blue organic electroluminescent devices of Examples 11 to 45 including the compound according to the present invention as an electron transport auxiliary layer material do not include an electron transport auxiliary layer and have an electron transport layer composed of Alq ₃ It was found that the organic electroluminescent device of Comparative Example 2 exhibited excellent performance in terms of current efficiency and driving voltage.

In addition, the blue organic electroluminescent devices of Examples 11 to 45 are similar to the compounds of the present application, but the compounds A and B in which a phenyl group is not disposed at the 1,3,4,5-position of the terphenyl center are used as an electron transport auxiliary layer Compared to Comparative Examples 3 and 4 included as a material, it was confirmed that it had a low driving voltage and high current efficiency.

Claims (15)

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

In Formula 1,
A plurality of X's are the same as or different from each other, and are each independently C(R ₁ ) or N, provided that at least one of the plurality of X's is N,
When R ₁ is plural, the plural R _1s are the same as or different from each other, and are each independently selected from hydrogen, heavy hydrogen, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, and C ₂ to 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, 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 ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ monoarylphosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group, C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, a C ₅ ~ C ₆₀ arylheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms;
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a C ₁ ~ C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, a C ₂ ~ C ₄₀ alkynyl group, a C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phospha Nyl group, C ₆ ~ C ₆₀ monoarylphosphinyl group, C ₆ ~ C ₆₀ diarylphosphinyl group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ arylheteroarylamine group and nuclear atom It is selected from the group consisting of 5 to 60 heteroarylamine groups, or they may combine with adjacent groups to form a condensed ring;
L is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
n and p are each an integer from 0 to 2,
an arylene group or a heteroarylene group of L; An _alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron of Ar 1 to Ar ₂ , and R ₁ Group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently hydrogen, heavy hydrogen (D), 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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, hetero having 5 to 60 nuclear atoms Aryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₅ ~ C ₆₀ It may be substituted with one or more substituents selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same as or different from each other. According to claim 1,
The X-containing ring is a compound selected from the group of substituents represented by the following formula:

In the above formula,
* means a site connected to Formula 1,
Z is O or S;
R ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms. According to claim 1,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents any one compound selected from the following structural formulas:

In the above formula,
* means a site connected to Formula 1 above. According to claim 1,
Wherein L is a single bond, or a compound represented by any one of Formulas 2 and 3 below:
[Formula 2]

[Formula 3]

In Formula 2 or 3,
* denotes a portion bonded to Formula 1,
Y is selected from the group consisting of O, S and Se,
m is an integer from 1 to 3; According to claim 5,
Formula 2 is a linker compound selected from the following structural formula.

In the above formula,
* means a part where the bond with Formula 1 is made. According to claim 5,
A compound in which Formula 3 is a linker selected from the following structural formula:

In the above formula,
* means a part where the bond with Formula 1 is made. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 4 to 7 below:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In the above formula,
X, Y, Ar ₁ , Ar ₂ , m, n and p are as defined in claim 1. According to claim 1,
The compound represented by Formula 1 is a compound represented by Formulas 8 to 13 below:
[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In the above formula,
L, Z, Ar ₂ , n and p are each as defined in claim 1. According to claim 1,
The compound represented by Formula 1 is a compound represented by Formulas 14 to 17 below:
[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Formulas 14 to 17,
X, L, Ar ₁ , Ar ₂ , and n are each as defined in claim 1. According to claim 1,
The compound represented by Formula 1 is a compound represented by Formulas 18 to 20 below:
[Formula 18]

[Formula 19]

[Formula 20]

In Chemical Formulas 18 to 20,
X, L, Ar ₁ , Ar ₂ , and n are each as defined in claim 1. According to claim 1,
The compound represented by Formula 1 is a material for a light emitting layer, an electron transport layer or an auxiliary electron transport layer. It 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 includes the compound according to any one of claims 1 to 12. electroluminescent device. According to claim 13,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer. According to claim 13,
The organic electroluminescent device wherein the compound is included as a material of at least one of a phosphorescent host material, an electron transport layer, and an electron transport auxiliary layer of the light emitting layer.