KR102686342B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is used as an organic layer material of an organic electroluminescent device, preferably an electron transport layer material and an electron transport auxiliary layer material, thereby emitting organic electroluminescence. The luminous efficiency, driving voltage, and lifespan of the device can be improved.

Description

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

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.

Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices'), which led to blue electroluminescence using anthracene single crystals in 1965, was conducted by Tang in 1987. (Tang) presented an organic EL device with a stacked structure divided into a hole layer and a light-emitting functional layer. Since then, in order to create high-efficiency, long-life organic EL devices, there has been development in the form of introducing each characteristic organic layer within the device, leading to the development of specialized materials used for this.

When a voltage is applied between two electrodes in an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Materials for forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials depending on the color of the light. In addition, yellow and orange luminescent materials are also used as luminescent materials to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

So far, hole injection layer and hole transport layer. As hole blocking layers and electron transport layers, NPB, BCP, Alq3, etc. expressed by the following chemical formulas are widely known, and as light emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. In particular, among light emitting materials, phosphorescent materials that have great advantages in terms of efficiency improvement include metal complex compounds containing Ir such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which are used as blue, green, and red dopant materials. , and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material. /

However, existing materials have advantages in terms of luminescence characteristics, but their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of lifespan in organic EL devices. Therefore, the development of organic layer materials with excellent performance is required.

However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

Republic of Korea Patent Publication No. 10-2015-0033082 (Publication date: 2015. 04. 01)

The purpose of the present invention is to provide a new organic compound that can be applied to organic electroluminescent devices and has excellent hole and electron injection and transport capabilities, luminescence ability, etc.

Another object of the present invention is to provide an organic electroluminescent device that includes the novel organic compound, exhibits low driving voltage, high luminous efficiency, and has improved lifespan.

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

[Formula 1]

In Formula 1,

R ₁ and R ₂ are the same or different from each other, are an aryl group with C ₆ to C ₆₀ or a heteroaryl group with 5 to 60 nuclear atoms, and can condense with each other to form a ring,

L ₁ and L ₂ are the same or different from each other, and are each independently a single bond or selected from the group consisting of an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,

A is a substituent represented by the following formula (2),

[Formula 2]

In Formula 2,

X ₁ to X ₃ are the same or different from each other, and are each independently C(R) or N, or at least one is N,

R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group with 3 to 40 atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, It is selected from the group consisting of a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and forms an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring with adjacent groups or a spiro bond can be achieved,

The R alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, aryl Phosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of Alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl is substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group; , when substituted with a plurality of substituents, these may be the same or different from each other,

Ar ₁ and Ar ₂ are the same or different from each other and are either an aryl group with C ₆ to C ₆₀ or a heteroaryl group with 5 to 60 nuclear atoms.

In the present invention, "alkyl" refers to an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers contains the compound of Formula 1. An organic electroluminescent device is provided.

In the present invention, “alkyl” is a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. etc., but is not limited to this.

In the present invention, “alkenyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond, examples of which include ethynyl. , 2-propynyl, etc., but is not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a monovalent ring in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule has non-aromaticity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, etc.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, contain heteroatoms selected from N, O, P, S, and Se in addition to carbon as ring forming atoms, and the entire molecule is non-aromatic. It is interpreted to include monovalent groups with aromaticity. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polyglycans such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl click hook; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

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

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

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.

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

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, is N, O, It is substituted with a hetero atom such as S or 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 60 carbon atoms.

“Condensed ring” in the present invention means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

When applied to an organic electroluminescent device, the organic light-emitting compound according to the present invention has excellent hole and electron injection and transport capabilities, and luminescence performance, has a low driving voltage and high luminous efficiency, and has the effect of improving lifespan.

Figure 1 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Figure 2 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. Novel organic compounds

The novel compound of the present invention may be represented by the following formula (1):

[Formula 1]

In Formula 1,
R ₁ and R ₂ are the same or different from each other, are an aryl group with C ₆ to C ₆₀ or a heteroaryl group with 5 to 60 nuclear atoms, and can condense with each other to form a ring,

L ₁ and L ₂ are the same or different from each other, and are each independently a single bond or selected from the group consisting of an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,

delete

A is a substituent represented by the following formula (2),

[Formula 2]

In Formula 2,

X ₁ to X ₃ are the same or different from each other, and are each independently C(R) or N, or at least one is N,

R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group with 3 to 40 atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, It is selected from the group consisting of a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and forms an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring with adjacent groups or a spiro bond can be achieved,

The R alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, aryl Phosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of Alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl is substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group; , when substituted with a plurality of substituents, these may be the same or different from each other,

Ar ₁ and Ar ₂ are the same or different from each other and are either an aryl group with C ₆ to C ₆₀ or a heteroaryl group with 5 to 60 nuclear atoms.
R ₁ or R ₂ of the compound represented by Formula 1 according to the present invention may be a substituent selected from the group consisting of R-1 to R-6 below.

delete

In R-1 to R-6, * is a portion where a bond is formed.

The L ₁ or L ₂ may be a single bond or a linker selected from L-1 to L-5 below.

In L-1 to L-5, * is the part where bonding takes place.

A in Formula 1 may be a substituent selected from the group consisting of A-1 to A-3 below.

In A-1 to A-3, * is a portion where bonding occurs.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto.

The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods (Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) ), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described later.

2. Organic electroluminescent device

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described 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 a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more types.

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 emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is represented by the formula (1) Contains compounds. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer, 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, and in this case, the host material may include the compound of Formula 1 above. Additionally, 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 light-emitting layer material of an organic electroluminescent device, preferably a blue, green, and red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer increases, thereby increasing the efficiency of the organic electroluminescent device. (Luminous efficiency and power efficiency), lifespan, brightness, and driving voltage 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, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Formula 1 of the present invention is a green phosphorescent exciplex N-type host material of a highly efficient 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, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. At this time, one or more of the hole injection layer, hole transport layer, auxiliary light emitting layer, light emitting layer, electron transport layer, and electron injection layer may include the compound represented by Formula 1, preferably a light emitting layer, more preferably a phosphorescent host. may include a compound represented by Formula 1 above. Meanwhile, an electron injection layer may be additionally laminated 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 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 above-mentioned organic material layer contains the compound represented by Formula 1 above. there is.

The organic material layer may be formed by vacuum deposition or solution application. 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 include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

Additionally, the anode material may be any cathode material known in the art without limitation. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

Additionally, as the anode material, any anode material known in the art may be used without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO2/Al, etc., but are not limited thereto.

Additionally, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and common materials known in the art can be used without limitation.

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

[Preparation Example 1] Synthesis of Core1

<Step 1> Synthesis of 9-benzhydryl-2-bromo-9H-fluoren-9-ol

Dissolve diphenylmethane (50 g, 297.2 mmol) in THF (500ml) under a nitrogen stream and cool to 0°C. Afterwards, 1.6M n-Butyllithium (186ml, 297.2mmol) was slowly added and stirred for 1 hour, then 2-bromo-9H-fluoren-9-one (69.3g 267.5mmol) was added and incubated at room temperature for 24 hours. Stirred. After completion of the reaction, the ammonium chloride aqueous solution was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, 9-benzhydryl-2-bromo-9H-fluoren-9-ol was obtained using column chromatography.

<Step 2> Synthesis of Core1

9-benzhydryl-2-bromo-9H-fluoren-9-ol and p-Toluenesulphonic acid (9.2g 53.5mmol) dissolved in 1L of toluene under a nitrogen stream were added, and refluxed and stirred at 100°C for 6 hours. After completion of the reaction, the temperature was lowered to room temperature, 10% NaHCO3 aqueous solution was added and stirred for 30 minutes, extracted with methylene chloride, _MgSO4 was added and filtered. After removing the solvent in the filtered organic layer, Core1 (42 g yield 70%) was obtained using column chromatography.

[LCMS] : 410

[Preparation Example 2] Synthesis of Core 2

Except for using 4-bromo-9H-fluoren-9-one instead of 2-bromo-9H-fluoren-9-one, the same process as [Preparation Example 1] was performed to obtain 40g of Core2 (yield 67%). got it

[LCMS] : 410

[Preparation Example 3] Synthesis of Core3

Dissolve 2,9-dibromo-9H-fluorene (50g, 154.31mmol) and 9-bromo-9H-fluorene (37.8g, 154.31mmol) KOH in a solvent mixed at a ratio of DMSO : MeOH = 8 : 2, then leave for 30 minutes. It was stirred for a while. Acetic acid was then added and stirred for 10 minutes, and then the reactant was poured into water. The precipitate produced at this time was filtered under reduced pressure and then recrystallized using Benzene and Ether to obtain 48 g of Core3 (yield 76%).

[LCMS]: 408

[Preparation Example 4] Synthesis of Core4

44 g of Core4 (yield 70%) was obtained by performing the same process as [Preparation Example 3] except that 4,9-dibromo-9H-fluorene was used instead of 2,9-dibromo-9H-fluorene.

[LCMS]: 408

[Preparation Example 5] Synthesis of Core 5

Except for using 3-bromo-9H-fluoren-9-one instead of 2-bromo-9H-fluoren-9-one, the same process as [Preparation Example 1] was performed to obtain 41g of Core5 (yield 69%). got it

[LCMS] : 410

[Preparation Example 6] Synthesis of Core6

45 g of Core6 (71% yield) was obtained by performing the same process as [Preparation Example 3] except that 3,9-dibromo-9H-fluorene was used instead of 2,9-dibromo-9H-fluorene.

[LCMS]: 408

[Synthesis Example 1] Synthesis of compound Inv 3

[Preparation Example 1] Core1 (5.0 g, 10.95 mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.5 g, 13.14 mmol), and Pd(OAc) ₂ ( 0.07 g, 0.32 mmol), Cs ₂ CO ₃ (7.1 g, 21.91 mmol), _and After completion of the reaction, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, Inv 3 (5.5 g, yield 78%), was obtained using column chromatography.

[LCMS] : 638

[Synthesis Example 2] Synthesis of compound Inv 7

Instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, use 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl- Except for using 1,3,5-triazine (5.5 g 13.14 mmol), the same process as [Synthesis Example 1] was performed to obtain the target compound, Inv 7 (5.8 g, yield 74%).

[LCMS] : 714

[Synthesis Example 3] Synthesis of compound Inv 14

2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine )-4,6-diphenyl-1,3,5-triazine (6.5g 13.14mmol) was used, and the same process as [Synthesis Example 1] was performed to prepare the target compound, Inv 14 (6.4 g, yield). 74%) was obtained.

[LCMS] : 790

[Synthesis Example 4] Synthesis of compound Inv 18

2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine The target compound, Inv 18 (5.5 g, yield 70%), was obtained by performing the same process as [Synthesis Example 1] except that -1,3,5-triazine (5.5 g 13.14 mmol) was used.

[LCMS] : 714

[Synthesis Example 5] Synthesis of compound Inv 103

Instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, use 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl- Except for using 1,3,5-triazine (5.7g 13.14mmol), the same process as [Synthesis Example 1] was performed to obtain the target compound, Inv 103 (5.9 g, yield 74%).

[LCMS] : 728

[Synthesis Example 6] Synthesis of compound Inv 145

4-([1,1'-biphenyl]-4-yl)-6-(6-chlorodibenzo[b,d] instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine The target compound, Inv 145 (6.4 g, yield 72%), was obtained by performing the same process as [Synthesis Example 1] except that furan-2-yl)-2-phenylpyrimidine (6.69 g 13.14 mmol) was used. .

[LCMS] : 803

[Synthesis Example 7] Synthesis of compound In 167

4-([1,1'-biphenyl]-4-yl)-6-(6-chlorodibenzo[b,d] instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine The target compound, Inv 167 (6.2 g, yield 70%), was obtained by performing the same process as [Synthesis Example 1] except that furan-2-yl)-2-phenylpyrimidine (5.5 g 13.14 mmol) was used. .

[LCMS] : 803

[Synthesis Example 8] Synthesis of compound Inv 182

Use Core2 instead of Core1 and 2-(4'-chloro-[1,1'-biphenyl]-3-yl)- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Except for using 4,6-diphenyl-1,3,5-triazine (5.5g 13.14mmol), the same process as [Synthesis Example 1] was performed to obtain the target compound, Inv 182 (5.7 g, yield 73%). ) was obtained.

[LCMS] : 714

[Synthesis Example 9] Synthesis of compound Inv 194

2-([1,1'-biphenyl]-4- instead of 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Except for using yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (5.5g 13.14mmol), the same process as [Synthesis Example 8] was performed to obtain the target compound. Inv 194 (5.5 g, 70% yield) was obtained.

[LCMS] : 714

[Synthesis Example 10] Synthesis of compound Inv 267

2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-(3-chlorophenyl)-2-phenyl-6- (4-(pyridin-3-yl)phenyl)pyrimidine (5.5g 13.14mmol) was used, and the same process as [Synthesis Example 8] was performed to obtain the target compound, Inv 267 (5.6 g, yield 71%). ) was obtained.

[LCMS] : 714

[Synthesis Example 11] Synthesis of compound Inv 276

Instead of 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, use 2-(4-chlorophenyl)-4-(dibenzo[b ,d]furan-4-yl)-6-phenyl-1,3,5-triazine (5.7g 13.14mmol) was used, and the same process as [Synthesis Example 8] was performed to prepare the target compound, Inv. 196 (5.8 g, yield 72%) was obtained.

[LCMS] : 728

[Synthesis Example 12] Synthesis of compound Inv311

2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3'-chloro-[1,1'- The above [ By performing the same process as in Synthesis Example 8, the target compound, Inv 311 (6.3 g, yield 71%) was obtained.

[LCMS]: 804

[Synthesis Example 13] Synthesis of compound Inv 327

2-(8-chlorodibenzo[b,d]furan-2 instead of 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine Except that -yl)-4,6-diphenyl-1,3,5-triazine (5.7g 13.14mmol) was used, the same process as [Synthesis Example 8] was performed to prepare the target compound, Inv 327 (5.9 g). , yield 74%) was obtained.

[LCMS] : 728

[Synthesis Example 14] Synthesis of compound Inv 346

2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4-(dibenzo[b,d]furan The target compound was obtained by performing the same process as [Synthesis Example 8] except that -3-yl)-6-(naphthalen-1-yl)-1,3,5-triazine (5.3g 13.14mmol) was used. Phosphorus Inv 346 (5.5 g, yield 71%) was obtained.

[LCMS] : 702

[Synthesis Example 15] Synthesis of compound Inv 356

2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(4'-chloro-[1,1'- The target compound, Inv, was prepared in the same manner as [Synthesis Example 8] except that biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (5.5 g 13.14 mmol) was used. 356 (5.7 g, yield 72%) was obtained.

[LCMS] : 714

[Synthesis Example 16] Synthesis of compound Inv 367

Use Core 3 instead of Core 1 and 2-(4''-chloro-[1,1':3',1' instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine The target compound was obtained by performing the same process as [Synthesis Example 1] except that '-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (6.5g 13.2mmol) was used. Phosphorus Inv 367 (6.1 g, yield 70%) was obtained.

[LCMS] : 788

[Synthesis Example 17] Synthesis of compound Inv 426

4-([1, Except for using 1'-biphenyl]-4-yl)-2-(4-chlorophenyl)-6-phenylpyrimidine (5.5g 13.2mmol), the same process as [Synthesis Example 16] was performed to obtain the target compound. Inv 426 (5.6 g, yield 71%) was obtained.

[LCMS] : 711

[Synthesis Example 18] Synthesis of compound Inv 451

2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(4-chlorophenyl )-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.7g 13.2 mmol), except that the same as [Synthesis Example 16] was used. The process was performed to obtain the target compound, Inv 263 (5.8 g, yield 72%).

[LCMS] : 726

[Synthesis Example 19] Synthesis of compound Inv 472

2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1, Using 1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (6.7g 13.2mmol) Except that, the same process as [Synthesis Example 16] was performed to obtain the target compound, Inv 472 (6.3 g, yield 71%).

[LCMS] : 802

[Synthesis Example 20] Synthesis of compound Inv 489

2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(6-chlorodibenzo [b,d]furan-2-yl)-4,6-diphenylpyrimidine (5.7 g 13.2 mmol) was used, and the same process as [Synthesis Example 16] was performed to prepare the target compound, Inv 489 (5.6 g). , yield 70%) was obtained.

[LCMS] : 725

[Synthesis Example 21] Synthesis of compound Inv 518

2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1, The same process as [Synthesis Example 16] was performed, except that 1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.5g 13.2mmol) was used. The target compound, Inv 518 (5.1 g, yield 72%) was obtained.

[LCMS] : 636

[Synthesis Example 22] Synthesis of compound Inv 533

Use Core4 instead of Core1 and 2-(3'-chloro-[1,1'-biphenyl]-4-yl)- instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine. Except for using 4,6-diphenyl-1,3,5-triazine (5.5g 13.2mmol), the same process as [Synthesis Example 1] was performed to obtain the target compound, Inv 533 (5.5 g, yield 70%). ) was obtained.

[LCMS] : 712

[Synthesis Example 23] Synthesis of compound Inv 555

2-([1,1'-biphenyl]-3- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine Except for using yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (5.5g 13.2mmol), the same process as [Synthesis Example 22] was performed to produce the target compound. Inv 555 (5.4 g, yield 69%) was obtained.

[LCMS] : 712

[Synthesis Example 24] Synthesis of compound Inv 618

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-(4-chlorophenyl)-2-phenyl-6- (4-(pyridin-3-yl)phenyl)pyrimidine (5.5g 13.2mmol) was used, and the same process as [Synthesis Example 22] was performed to obtain the target compound, Inv 618 (5.6 g, yield 71%). ) was obtained.

[LCMS] : 712

[Synthesis Example 25] Synthesis of compound Inv 626

Instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine, use 2-(4-chlorophenyl)-4-(dibenzo[b ,d]furan-2-yl)-6-phenyl-1,3,5-triazine (5.7g 13.2mmol) was used, and the same process as [Synthesis Example 22] was performed to prepare the target compound, Inv. 626 (5.7 g, yield 71%) was obtained.

[LCMS] : 726

[Synthesis Example 26] Synthesis of compound Inv 658

2-(6-chlorodibenzo[b,d]thiophen-2 instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine Except that -yl)-4,6-diphenyl-1,3,5-triazine (5.9g 13.2mmol) was used, the same process as [Synthesis Example 22] was performed to prepare the target compound, Inv 658 (5.9 g). , yield 72%) was obtained.

[LCMS] : 742

[Synthesis Example 27] Synthesis of compound Inv 685

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-([1,1'-biphenyl]-4- The purpose was performed in the same manner as in [Synthesis Example 22], except that yl)-6-(7-chlorodibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (6.7g 13.2mmol) was used. The compound Inv 658 (6.5 g, yield 73%) was obtained.

[LCMS] : 801

[Synthesis Example 28] Synthesis of compound Inv 697

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4-(dibenzo[b,d]furan The target compound was obtained by carrying out the same process as [Synthesis Example 22] except that -3-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (5.3g 13.2mmol) was used. Phosphorus Inv 374 (5.7 g, yield 74%) was obtained.

[LCMS] : 700

[Synthesis Example 29] Synthesis of compound Inv 712

Use Core5 instead of Core1 and 2,4-di([1 ,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (5.5g 13.2mmol) was used, and the same process as [Synthesis Example 1] was performed to produce the target compound. Inv 712 (5.6 g, yield 71%) was obtained.

[LCMS] : 714

[Synthesis Example 30] Synthesis of compound Inv 730

Use Core6 instead of Core1 and 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3'-chloro- [1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (5.5g 13.2mmol) was used in the same process as [Synthesis Example 1]. This was performed to obtain the target compound, Inv 730 (5.5 g, yield 70%).

[LCMS] : 714

[Examples 1 to 25] Fabrication of green organic EL device

Compounds Inv 3 to Inv 730 synthesized in the synthesis example were purified to high purity by sublimation according to a commonly known method, and then a green organic EL device was manufactured according to the process below.

First, ITO (Indium tin oxide) is 1,500 The glass substrate coated with a thin film was ultrasonically cleaned with distilled water. After cleaning 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), cleaning the substrate for 5 minutes using UV, and vacuum evaporation. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/each compound of Inv 3 to Inv 730 + 10% Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm) An organic EL device was manufactured by stacking in the following order: nm)/LiF (1 nm)/Al (200 nm).

[Comparative Example 1] Fabrication of green organic EL device

The green organic EL device of Comparative Example 1 was manufactured in the same process as Example 1, except that CBP was used instead of compound Inv3 as the light-emitting host material when forming the light-emitting layer.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP, and BCP used in Examples 1 to 30 and Comparative Example 1 are as follows.

[Evaluation Example 1]

The driving voltage, current efficiency, and luminescence peak at a current density (10) mA/cm2 were measured for each green organic EL device manufactured in Examples 1 to 30 and Comparative Example, and the results are shown in Table 1 below. .

Sample host driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 Inv3 3.8 456 64.2 Example 2 Inv7 3.9 455 65.4 Example 3 Inv14 3.6 455 66.2 Example 4 Inv18 3.7 456 64.5 Example 5 Inv103 3.9 457 66.9 Example 6 Inv145 3.8 454 64.2 Example 7 Inv167 4.0 458 68.3 Example 8 Inv182 3.8 457 66.4 Example 9 Inv194 3.7 456 61.1 Example 10 Inv267 3.9 455 62.8 Example 11 Inv276 3.8 454 62.2 Example 12 Inv311 4.0 457 63.3 Example 13 Inv327 4.2 455 61.4 Example 14 Inv346 3.9 458 61.9 Example 15 Inv356 4.1 459 62.8 Example 16 Inv367 4.2 456 60.6 Example 17 Inv426 4.5 457 59.7 Example 18 Inv451 3.9 455 58.4 Example 19 Inv472 4.1 454 59.2 Example 20 Inv489 4.1 458 58.8 Example 21 Inv518 4.2 457 60.2 Example 22 Inv533 4.0 457 59.4 Example 23 Inv555 4.3 456 58.8 Example 24 Inv618 4.1 454 58.6 Example 25 Inv626 4.2 455 57.2 Example 26 Inv658 3.8 454 62.2 Example 27 Inv685 4.0 457 63.3 Example 28 Inv697 4.2 455 61.4 Example 29 Inv712 3.9 458 61.9 Example 30 Inv730 4.1 459 62.8 Comparative Example 1 CBP 5.6 459 42.6

As shown in Table 1, the green organic EL devices of Examples 1 to 30 using the compounds Inv 3 to Inv 730 according to the present invention as the emitting layer are different from the green organic EL devices using Comparative Example 1 using conventional CBP as the emitting layer. In comparison, it was found that it showed better performance in terms of efficiency and driving voltage.

[Examples 31 to 40] Fabrication of blue organic electroluminescent device

Compounds Inv 3 to Inv 712 synthesized in the synthesis example were purified by sublimation to high purity according to a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring 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 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30nm)/ each of Inv 3 to Inv 712. An organic electroluminescent device was manufactured by stacking compounds (30 nm)/LiF (1 nm)/Al (200 nm) in that order.

The structures of NPB, ADN, and Alq3 used at this time are as follows.

[Comparative Example 2] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 31, except that Alq3 was deposited at 30 nm instead of Inv 7 as the electron transport layer material.

[Evaluation Example 2]

For each blue organic electroluminescent device manufactured in Examples 31 to 40 and Comparative Example 2, the driving voltage, current efficiency, and luminescence peak at a current density (10) mA/cm2 were measured, and the results are shown in Table 2 below. indicated.

Sample electron transport layer driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 31 Inv3 4.0 458 7.0 Example 32 Inv18 4.1 459 7.0 Example 33 Inv194 3.8 459 6.9 Example 34 Inv346 3.9 459 7.0 Example 35 Inv356 3.8 459 7.1 Example 36 Inv426 3.7 458 7.1 Example 37 Inv451 4.2 459 7.1 Example 38 Inv518 3.8 459 7.2 Example 39 Inv626 3.9 458 7.0 Example 40 Inv697 4.1 459 6.9 Comparative Example 2 Alq ₃ 4.8 460 5.8

As shown in Table 2, the blue organic electroluminescent device of Examples 31 to 40 in which the compound of the present invention was applied as the electron transport layer compared to the blue organic electroluminescent device of Comparative Example 2 in which conventional Alq ₃ was used as the electron transport layer. , it was found to exhibit excellent performance in terms of driving voltage, luminescence peak, and current efficiency.

[Examples 41 to 60] Preparation of blue organic electroluminescent device

The compounds Inv 7 to Inv 730 synthesized in the synthesis example were purified by sublimation to high purity according to a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

ITO (Indium tin oxide) is 1,500 The glass substrate coated with a thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm) / each compound of Inv 7 to Inv 730 (30 nm) )/Alq3 (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in that order to manufacture an organic electroluminescent device.

The structures of NPB, ADN, and Alq3 used at this time are as follows.

[Comparative Example 3] Preparation of blue organic electroluminescent device

Blue organic electroluminescence was produced in the same manner as in Example 41, except that Inv7, which was used as the electron transport auxiliary layer material in Example 41, was not used, and Alq3, the electron transport layer material, was deposited at 30 nm instead of 25 nm. The device was manufactured.

[Evaluation Example 3]

For the organic electroluminescent devices manufactured in Examples 41 to 60 and Comparative Example 3, the driving voltage, emission wavelength, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm2, and the results are shown in Table 3 below. indicated.

Sample electronic transport
auxiliary floor driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 41 Inv7 4.3 6.8 457 Example 42 Inv14 4.0 7.2 458 Example 43 Inv103 4.1 7.3 458 Example 44 Inv145 3.9 7.4 457 Example 45 Inv167 4.0 7.2 458 Example 46 Inv182 4.4 7.1 458 Example 47 Inv267 4.3 7.2 458 Example 48 Inv276 4.1 7.3 458 Example 49 In311 4.2 7.2 458 Example 50 Inv327 4.1 7.2 457 Example 51 Inv367 4.3 7.1 458 Example 52 Inv472 4.0 7.0 458 Example 53 Inv489 4.2 7.5 458 Example 54 Inv533 4.3 7.1 458 Example 55 Inv555 4.0 7.2 458 Example 56 Inv618 4.0 7.1 458 Example 57 Inv658 4.4 7.0 458 Example 58 Inv685 4.3 7.1 458 Example 59 Inv713 4.1 7.4 457 Example 60 Inv730 4.2 7.0 458 Comparative Example 3 - 4.7 5.6 457

As shown in Table 3, the blue organic electroluminescent devices of Examples 41 to 60 in which the compound according to the present invention was applied as an electron transport auxiliary layer were those of Comparative Example 3 including an electron transport layer made of Alq ₃ without an electron transport auxiliary layer. Compared to organic electroluminescent devices, it was found to exhibit excellent performance in terms of current efficiency and driving voltage.

10: anode 20: cathode
30: Organic layer 31: Hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (7)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R ₁ and R ₂ are the same or different from each other, are an aryl group of C ₆ to C ₆₀ , or a heteroaryl group of 5 to 60 nuclear atoms, and may condense with each other to form a ring,
L ₁ and L ₂ are the same or different from each other, and are each independently a single bond or selected from the group consisting of an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,
A is a substituent represented by the following formula (2),
[Formula 2]

In Formula 2,
X ₁ to X ₃ are the same or different from each other, and are each independently C(R) or N, or at least one is N,
R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group with 3 to 40 atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, It is selected from the group consisting of a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and forms an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring with adjacent groups or a spiro bond can be achieved,
The R alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, aryl Phosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of Alkynyl group, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryl Amine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl is substituted or unsubstituted with one or more substituents selected from the group consisting of a boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group; , when substituted with a plurality of substituents, these may be the same or different from each other,
Ar ₁ and Ar ₂ are the same or different from each other and are either an aryl group with C ₆ to C ₆₀ or a heteroaryl group with 5 to 60 nuclear atoms. According to paragraph 1,
A compound characterized in that R ₁ or R ₂ is a substituent selected from the group consisting of R-1 to R-6 below:

In R-1 to R-6, * is a portion where a bond is formed. According to paragraph 1,
A compound characterized in that L ₁ or L ₂ is a single bond or a linker selected from the following L-1 to L-5:

In L-1 to L-5,
* is the part where the combination takes place. According to paragraph 1,
A compound of Formula 1 is characterized in that A is a substituent selected from the group consisting of A-1 to A-3 below:

In A-1 to A-3, * is a portion where bonding occurs. According to paragraph 1,
The compound is characterized in that it is selected from the group consisting of the following compounds.










































An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes the compound represented by the formula (1) of claim 1. According to clause 6,
The organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.