KR102617613B1 - Organic compounds and organic electro luminescence device comprising 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 in the organic material layer, preferably the light-emitting layer, of the organic electroluminescent device, thereby improving the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device. etc. can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING 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 the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a hole layer and a functional layer of the light-emitting layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. 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 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.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve 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. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

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

However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their 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.

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

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

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

[Formula 1]

In Formula 1,

X ₁ to X ₄ are each independently N or C(R ₂ );

R ₁ and R ₂ are each independently substituents represented by the following formula (2), and when R ₂ is plural, they are the same or different from each other;

[Formula 2]

In Formula 2,

* refers to the part where the combination takes place;

L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₃ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The arylene group and heteroarylene group of L ₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R ₃ , Alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group, and two adjacent R The aromatic ring, non-aromatic condensed polycyclic ring, aromatic hetero ring and non-aromatic condensed hetero polycyclic ring formed by combining ₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~ C ₆₀ arylsilyl group, and when substituted with a plurality of substituents, they are the same or different from each other.

The present invention provides an organic electroluminescent device comprising 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 of Formula 1. .

In the present invention, “alkyl” is a monovalent substituent derived from a straight or branched 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.

“Heteroaryl” in the present invention 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.

In the present invention, “aromatic ring” 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. Examples of such aromatic rings include, but are not limited to, phenyl, naphthyl, phenanthrenyl, and anthrenyl.

In the present invention, "non-aromatic condensed polycyclic" refers to a polycyclic ring in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom, and has non-aromaticity as a whole. refers to a group (eg, having 8 to 60 carbon atoms). Examples of the non-aromatic condensed polycyclic ring may include, but are not limited to, a fluorenyl group.

“Aromatic heterocycle” in the present invention means 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, and contain heteroatoms selected from N, O, P, S, and Se in addition to carbon as ring forming atoms. 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, "non-aromatic condensed heteropolycyclic" means that two or more rings are condensed with each other, and includes a hetero atom selected from N, O, P and S in addition to carbon as a ring forming atom, and the entire molecule is It refers to a group having non-aromaticity (for example, having 2 to 60 carbon atoms). Examples of the non-aromatic condensed heteropolycyclic ring may include, but are not limited to, a carbazolyl group.

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

Since the compound of the present invention has excellent thermal stability, carrier transport ability, luminescence ability, etc., it can be usefully applied as an organic layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device containing the compound of the present invention in the organic material layer has greatly improved aspects such as luminous performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full color display panels.

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 new compound of the present invention can be represented by the following formula (1):

[Formula 1]

In Formula 1,

X ₁ to X ₄ are each independently N or C(R ₂ );

R ₁ and R ₂ are each independently substituents represented by the following formula (2), and when R ₂ is plural, they are the same or different from each other;

[Formula 2]

In Formula 2,

* refers to the part where the combination takes place;

L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₃ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The arylene group and heteroarylene group of L ₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R ₃ , Alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group, and two adjacent R The aromatic ring, non-aromatic condensed polycyclic ring, aromatic hetero ring and non-aromatic condensed hetero polycyclic ring formed by combining ₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~ C ₆₀ arylsilyl group, and when substituted with a plurality of substituents, they are the same or different from each other.

In the present invention, the compound represented by Formula 1 has excellent EWG (electronwithdrawing froup) properties, is electrochemically stable compared to the previously known 6-membered heterocyclic structure, has excellent electron mobility, and has a high glass transition temperature and Excellent thermal stability. For this reason, since the compound represented by Formula 1 of the present invention has excellent electron transport ability and luminescence properties, it can be used in any one of the organic material layers of the organic electroluminescent device: a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. It can be used as a material. Preferably, it can be used as a material for any one of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer additionally laminated on the electron transport layer, and more preferably, the material for the electron transport layer or the electron transport auxiliary layer.

Therefore, when the compounds having the structure of Formula 1 of the present invention are used in an organic electroluminescent device, not only can they be expected to have excellent thermal stability and carrier transport ability (especially electron transport ability and luminescence ability), but also to improve the driving voltage, efficiency, and lifespan of the device. etc. can be improved, and due to high triplet energy, excellent efficiency can be achieved as a material for the latest organic electroluminescent devices.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by Formula 3 or 4 below:

[Formula 3]

[Formula 4]

In Formulas 3 and 4 above,

R ₁ and R ₄ to R ₇ may each independently be a substituent represented by Formula 2 above.

According to a preferred embodiment of the present invention, one or more of R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and R ₁ are bonded to each other to form an aromatic ring having 5 to 50 nuclear atoms. , forming a non-aromatic condensed polycycle having 5 to 50 nuclear atoms, an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle having 5 to 50 nuclear atoms;

The aromatic ring, non-aromatic condensed polycycle, aromatic heterocycle and non-aromatic condensed heteropolycyclic ring formed by combining R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and R ₁ are each Independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, number of nuclear atoms 5 to 60 heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₁ to C ₄₀ alkylsulfonyl group, C ₆ to C ₆₀ arylsulfonyl group, C ₆ ~C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ aryl It is substituted or unsubstituted with one or more substituents selected from the group consisting of a carbonyl group and a C ₆ to C ₆₀ arylsilyl group, and when substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by Formula 3 or 4, one or more of R ₄ and R ₅ , R ₅ and R ₆ , and R ₆ and R ₇ are each independently represented by the following Formulas 5 to 9: Can form a condensed ring with a ring represented by any of:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 5 to 9,

The dotted line indicates the part where condensation takes place;

Y ₁ to Y ₄ are each independently N or C(Ar ₁ ), and when there are multiple Ar _1s , they are the same or different from each other;

X ₅ is O, N, C(Ar ₂ )(Ar ₃ ), S or Si(Ar ₄ )(Ar ₅ );

Ar ₁ to Ar ₅ and R ₈ to R ₁₃ are each independently a substituent represented by the following formula (10);

[Formula 10]

In Formula 10 above,

* refers to the part where the combination takes place;

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

R ₁₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The alkyl group, _alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other.

According to a preferred embodiment of the present invention, the ring represented by Formula 5 may be represented by the following Formula 11 or 12:

[Formula 11]

[Formula 12]

In Formulas 11 and 12 above,

The dotted line indicates the part where condensation takes place;

R ₁₅ to R ₁₈ are each independently a substituent represented by the following formula (13);

[Formula 13]

In Formula 13 above,

* refers to the part where the combination takes place;

L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other.

According to a preferred embodiment of the present invention, in the ring represented by Formula 6, R ₈ and R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 5 nuclear atoms 60 heteroaryl groups, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ selected from the group consisting of a C ₆₀ mono or diarylphosphinyl group, a C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group,

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₈ and R ₉ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the ring represented by Formula 6 may be represented by the following Formula 14:

[Formula 14]

In Formula 14 above,

The dotted line indicates the part where condensation takes place;

R ₂₀ to R ₂₄ are each independently a substituent represented by the following formula (13);

[Formula 13]

In Formula 13 above,

* refers to the part where the combination takes place;

L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other.

According to a preferred embodiment of the present invention, in the ring represented by Formula 7, X ₅ is O, N, C(Ar ₂ )(Ar ₃ ), S, or Si(Ar ₄ )(Ar ₅ );

Here, Ar ₂ to Ar ₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ is selected from the group consisting of an alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group;

Ar ₂ to Ar ₅ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, aryl Sulfonyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, alkyl carbonyl group, aryl carbonyl group, and aryl silyl 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 alkynyl group, C ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ A group consisting of arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, the ring represented by Formula 7 may be represented by the following Formula 15 or 16:

[Formula 15]

[Formula 16]

In Formulas 15 and 16 above,

The dotted line indicates the part where condensation takes place;

R ₂₅ to R ₃₆ are each independently a substituent represented by the following formula (13);

[Formula 13]

In Formula 13 above,

* refers to the part where the combination takes place;

L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, They may be the same or different from each other;

X ₅ is as defined in Formula 7 above.

According to a preferred embodiment of the present invention, in the compound represented by Formula 4, R ₇ and R ₁ are combined with each other to form an aromatic ring having 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring having 5 to 50 nuclear atoms, It may form an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle having 5 to 50 nuclear atoms, and specific examples thereof may be represented by the following formula 17 or 18, but are not limited thereto. :

[Formula 17]

[Formula 18]

In Formulas 17 and 18 above,

B ₁ and B ₂ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, or a heteroaryl group with 5 to 60 nuclear atoms, or are combined with each other to form an aromatic ring with 5 to 50 nuclear atoms. , forming a non-aromatic condensed polycycle with 5 to 50 nuclear atoms, an aromatic hetero ring with 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle with 5 to 50 nuclear atoms;

The aromatic ring, non-aromatic condensed polycycle, aromatic hetero ring and non-aromatic condensed hetero polycycle formed by combining the alkyl group, aryl group and heteroaryl group of B ₁ and B ₂ and B ₁ and B ₂ are each independently deuterium. , halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ to C ₆₀ arylsilyl groups, and when substituted with a plurality of substituents, they may be the same or different from each other;

A ₁ to A ₉ are each independently a substituent represented by the following formula (19);

[Formula 19]

In Formula 19 above,

* refers to the part where the combination takes place;

L ₄ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₃₇ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;

The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other.

According to a preferred embodiment of the present invention, L ₁ to L ₄ may each independently be selected from the group consisting of a phenylene group, a biphenylene group, a naphthalenyl group, a quinazolinyl group, and a carbazolyl group.

According to a preferred embodiment of the present invention, L ₁ to L ₄ may each independently be a linker represented by any one of the following formulas A-1 to A-6:

In the above formulas A-1 to A-6,

* refers to the part where the combination takes place;

q is an integer from 0 to 4;

A ₁₀ is 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, nuclear atom Heterocycloalkyl group with 3 to 40 atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ selected from the group consisting of an arylcarbonyl group and an arylamine group having C ₆ to C ₆₀ , and when there are more than one A ₁₀ , they are the same or different from each other;

Z ₁ to Z ₈ are each independently N or C(Ar ₆ );

In Formula A-3, any one of Z ₁ to Z ₄ and any one of Z ₅ to Z ₈ that is bonded as a linker is C(Ar ₆ ), wherein Ar ₆ is absent;

In Formula A-4, any two of Z ₁ to Z ₄ bonded as a linker are C(Ar ₆ ), and Ar ₆ is absent;

X ₆ is each independently O, S, N(Ar ₇ ) or C(Ar ₈ )(Ar ₉ );

X ₇ is N or C(Ar ₁₀ );

Ar ₆ to Ar ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkyl carbo selected from the group consisting of a nyl group, an arylcarbonyl group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , and when there is a plurality of Ar ₆ , they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl sulfo of A ₁₀ and Ar ₆ to Ar ₁₀ Nyl group, arylsulfonyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, aryl carbonyl group, and aryl silyl group are each independently a deuterium, halogen, cyano, or nitro group. , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ Arylphosphanyl group of C ₆₀ , mono or diarylphosphinyl group of C ₆ ~ C ₆₀ , alkylcarbonyl group of C ₁ ~ C ₄₀ , arylcarbonyl group of C ₆ ~ C ₆₀ and arylsilyl of C ₆ ~ C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, any one of R ₁ , R ₃ , R ₁₄ , R ₁₉ and R ₃₇ is a C ₂ to C ₄₀ alkenyl group, a C ₆ to C ₆₀ aryl group, or the number of nuclear atoms. 5 to 60 heteroaryl groups, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylsulfonyl group, C ₆ to C ₆₀ arylsulfonyl group, C ₁ ~C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkyl selected from the group consisting of a carbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group,

The alkenyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, of R ₁ , R ₃ , R ₁₄ , R ₁₉ and R ₃₇ Arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group are each independently halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C When unsubstituted or substituted with one or more substituents selected from the group consisting of an alkynyl group of ₂ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms, and substituted with a plurality of substituents, These may be the same or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₁ and R ₃ is each independently an alkenyl group of C ₂ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , or a heteroaryl group of 5 to 60 nuclear atoms. group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ selected from the group consisting of a C ₆₀ arylcarbonyl group and a C ₆ to C ₆₀ arylamine group,

The alkenyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diaryl of R ₁ and R ₃ Phosphinyl group, alkylcarbonyl group, arylcarbonyl group, and arylsilyl group are each independently halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C It is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups having ₆ to C ₆₀ and heteroaryl groups having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁₄ is an alkenyl group of C ₂ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, alkyl of C ₃ to C ₄₀ Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl Boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~C ₆₀ selected from the group consisting of arylamine groups,

The alkenyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group of R ₁₄ , alkylcarbonyl group, arylcarbonyl group, and arylsilyl group are each independently halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having ₆₀ atoms and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁₉ is an alkenyl group of C ₂ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, alkyl of C ₃ to C ₄₀ Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl Boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~C ₆₀ selected from the group consisting of arylamine groups,

The alkenyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group of R ₁₉ , alkylcarbonyl group, arylcarbonyl group, and arylsilyl group are each independently halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having ₆₀ atoms and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₃₇ is an alkenyl group of C ₂ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, alkyl of C ₃ to C ₄₀ Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl Boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~C ₆₀ selected from the group consisting of arylamine groups,

The alkenyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group of R ₃₇ , alkylcarbonyl group, arylcarbonyl group, and arylsilyl group are each independently halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having ₆₀ atoms and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₁ , R ₃ , R ₁₄ , R ₁₉ and R ₃₇ may each independently be a substituent represented by any one of the following formulas B-1 to B-7. :

In the above formulas B-1 to B-7,

Z ₉ to Z ₁₃ are each independently N or C(B ₄ );

In Formula B-4, any one of Z ₉ to Z ₁₂ bonded as a substituent is C(Ar ₁₁ ), and in this case, Ar ₁₁ is absent;

T ₁ and T ₂ are each independently a single bond, C(Ar ₁₂ )(Ar ₁₃ ), N(Ar ₁₄ ), O, S, S(=O)(=0), B(Ar ₁₅ ), and Si( Ar ₁₆ )(Ar ₁₇ ), but both T ₁ and T ₂ are not single bonds;

T ₃ is N(Ar ₁₈ ) or O;

r and s are each independently integers from 0 to 4;

A ₁₁ and A ₁₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, selected from the group consisting of an arylcarbonyl group of C ₆ to C ₆₀ and an arylamine group of C ₆ to C ₆₀ , and when each of A ₁₁ and A ₁₂ is plural, they are the same or different from each other;

B ₃ , B ₄ and Ar ₁₁ to Ar ₁₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ is selected from the group consisting of an alkylcarbonyl group of ~C ₄₀ , an arylcarbonyl group of _C6 ~ _C60 , and an arylamine group of _C6 ~ _C60 , and when there are multiple B ₄ and Ar ₁₁ to Ar ₁₈ , they are each other. identical or different;

A ₁₁ , A ₁₂ , B ₃ , B ₄ and Ar ₁₁ to Ar ₁₈ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group are each independently deuterated. , halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ to C ₆₀ arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

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 electric field light emitting element

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.

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, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic material layers has the formula above. It may include a compound represented by 1.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, but referring to Figure 1 as an example, for example, an anode 10 and a cathode 20 facing each other, and the anode 10 and the cathode ( 20) and includes an organic layer 30 located between them. Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.

Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode. An electron injection layer 36 may be further included between (20).

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 not only improves the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31. Rather, it is a layer that is applied on top of the ITO, which has an uneven surface, and functions to smooth the surface of the ITO. It can be used without particular restrictions as long as it is commonly used in the art. For example, an amine compound can be used. It is not limited to this.

In addition, the electron injection layer 36 is a layer that is laminated on the top of the electron transport layer to facilitate electron injection from the cathode and ultimately improves power efficiency. If it is commonly used in the art, it is a special layer. It can be used without limitation, and for example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO, etc. can be used.

In addition, although not shown in the drawings, in the present invention, a light-emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light-emitting layer 32. The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer 32 and adjust the thickness of the organic layer 30. The light emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport layer 31.

In addition, although not shown in the drawings, in the present invention, a lifespan improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light-emitting device to the light-emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer and cannot diffuse or move to the electron transport layer, thereby limiting the holes to the light-emitting layer. . This function of limiting holes to the light-emitting layer prevents holes from diffusing into the electron transport layer, which moves electrons through reduction, and suppresses the phenomenon of lifespan reduction through irreversible decomposition reactions due to oxidation, contributing to improving the lifespan of organic light-emitting devices. You can.

In the present invention, the compound represented by Formula 1 has excellent EWG (electronwithdrawing froup) properties, is electrochemically stable compared to the previously known 6-membered heterocyclic structure, has excellent electron mobility, and has a high glass transition temperature and Excellent thermal stability. For this reason, since the compound represented by Formula 1 of the present invention has excellent electron transport ability and luminescence properties, it can be used in any one of the organic material layers of the organic electroluminescent device: a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. It can be used as a material. Preferably, it can be used as a material for any one of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer additionally laminated on the electron transport layer. More preferably, it can be used as a material for the electron transport layer or the electron transport auxiliary layer.

In addition, when using the compound according to the present invention as a light-emitting layer material, specifically, the compound represented by Formula 1 can be used as a phosphorescent host, fluorescent host, or dopant material of the light-emitting layer, preferably a phosphorescent host (blue, green) and/or a red phosphorescent host material).

In addition, in the present invention, the organic electroluminescent device not only includes an anode, one or more organic material layers, and a cathode sequentially stacked as described above, but may additionally include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic layers (e.g., electron transport auxiliary layer) includes the compound represented by Formula 1 above. It can be manufactured by forming other organic layers and electrodes.

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.

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material may be made of, for example, a conductor with a high work function to facilitate hole injection, and may 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.

In addition, the cathode material can be made of a conductor with a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. Same metals or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

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

[ Preparation example 1] Synthesis of A-1

At room temperature, hydrazine monohydrate (0.75 g, 15 mmol), acetic acid (0.06 g, 1 mmol), 1-(6-chloropyridin-2-yl)ethan-1-one (1.55 g, 10 mmol), ethanol ( 50 ml) were mixed and then heated and stirred for 6 hours. Then, EtOAc (250 ml), ethanol (50 ml), and Cu(OAc) ₂ (0.09 g, 0.5 mmol) were added and stirred at 60°C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, extracted with EtOAc, then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, the target compound A-1 (1.17 g, yield 70%) was obtained using column chromatography.

¹ H-NMR: δ 2.38 (s, 3H), 7.30 (d, 1H), 7.95 (m, 2H)

[ Preparation example 2] Synthesis of A-2

[Preparation] except that (5-chloropyridin-2-yl)(phenyl)methanone (2.17 g, 10 mmol) was used instead of 1-(6-chloropyridin-2-yl)ethan-1-one as a reactant. By performing the same process as in Example 1, the target compound A-2 (1.58 g, yield 69%) was obtained.

¹ H-NMR: δ 7.53 (m, 4H), 7.84 (m, 2H), 7.99 (d, 1H), 8.79 (s, 1H)

[ Preparation example 3] Synthesis of A-3

[Preparation] except that (3-chlorophenyl)(pyridin-2-yl)methanone (2.17 g, 10 mmol) was used instead of 1-(6-chloropyridin-2-yl)ethan-1-one as a reactant. By performing the same process as in Example 1, the target compound A-3 (1.56 g, yield 68%) was obtained.

¹ H-NMR: δ 7.36 (t, 1H), 7.48 (m, 2H), 7.60 (d, 1H), 7.72 (d, 1H), 7.97 (s, 1H), 8.59 (d, 1H), 8.98 ( t, 1H)

[ Preparation example 4] Synthesis of A-4

[ By performing the same process as [Preparation Example 1], the target compound A-4 (1.54 g, yield 67%) was obtained.

¹ H-NMR: δ 7.28 (t, 1H), 7.52 (m, 2H), 7.98 (m, 2H), 8.83 (d, 1H), 9.25 (d, 1H)

[ Preparation example 5] Synthesis of A-5

[Preparation Example 1] except that 6-chloroquinolinine-2-carbaldehyde (1.91 g, 10 mmol) was used as a reactant instead of 1-(6-chloropyridin-2-yl)ethan-1-one The same process was performed to obtain target compound A-5 (1.34 g, yield 66%).

¹ H-NMR: δ 7.26 (d, 1H), 7.70 (m, 2H), 7.95 (m, 2H), 8.45 (d, 1H)

[ Preparation example 6] Synthesis of A-6

[ By performing the same process as in Preparation Example 1, the target compound A-6 (1.81 g, yield 65%) was obtained.

¹ H-NMR: δ 7.50 (m, 4H), 7.66 (m, 2H), 7.98 (m, 2H), 8.11 (d, 1H), 9.15 (s, 1H)

[ Preparation example 7] Synthesis of A-7

[ By performing the same process as in Preparation Example 1, the target compound A-7 (2.79 g, yield 64%) was obtained.

¹ H-NMR: δ 7.62~7.65 (m, 6H), 7.98 (m, 3H), 8.45 (d, 1H)

[ Preparation example 8] Synthesis of A-8

Except that (2-chlorophenanthridin-6-yl)(phenyl)methanone (3.17 g, 10 mmol) was used as a reactant instead of 1-(6-chloropyridin-2-yl)ethan-1-one. The same process as [Preparation Example 1] was performed to obtain the target compound A-8 (2.07 g, yield 63%).

¹ H-NMR: δ 7.50 (m, 6H), 7.86 (m, 6H)

[ Preparation example 9] Synthesis of A-9

5-chloro-7H-indeno[2,1-c]isoquinolin-7-one (2.65 g, 10 mmol) was used as a reactant instead of 1-(6-chloropyridin-2-yl)ethan-1-one. The target compound A-9 (1.72 g, yield 62%) was obtained by performing the same process as [Preparation Example 1] except that.

¹ H-NMR: δ 7.70 (m, 2H), 7.81 (d, 1H), 8.10 (d, 2H), 8.42 (m, 3H)

[ Preparation example 10] Synthesis of A-10

[1,2,3]triazolo[1,5-a]quinoline (0.99 g, 5.91 mmol) was dissolved in 15 mL of THF and cooled to -78°C. 1.5M n-BuLi (7.88 mL, 11.84 mmol) was added dropwise here, stirred for 2 hours, and then iodine (6.09 g, 24 mmol) dissolved in 10 mL of THF was added dropwise. After the dropwise addition, the temperature was gradually raised to room temperature, stirred for 2 hours, and then recrystallized from dichloromethane to obtain the target compound, A-10 (1.51 g, yield 61%).

¹ H-NMR: δ 7.20 (m, 2H), 7.81 (d, 1H), 8.24 (m, 2H)

[ Preparation example 11] Synthesis of A-11

<Step 1> 2-(3-(2-(3- Chlorobenzoyl )phenyl) Triaz -2-N-1-Day) of acetonitrile synthesis

Add sodium nitrate (0.68 g, 10 mmol) and HCl (0.8 ml) to (2-aminophenyl)(3-chlorophenyl)methanone (2.31 g, 10 mmol) to make diazonium salt, and then add amino phenyl (3-chlorophenyl)methanone (2.31 g, 10 mmol). Acetonitrile bisulfate (1.54 g, 10 mmol) was added and reacted for 0.5 hours. After completion of the reaction, it was neutralized with aqueous sodium carbonate solution while stirring for 2 hours. The product was filtered and recrystallized to obtain the target compound, 2-(3-(2-(3-chlorobenzoyl)phenyl)triaz-2-en-1-yl)acetonitrile (1.70 g, yield 57%).

¹ H-NMR: δ 3.77 (s, 2H), 7.34 (d, 1H), 7.55 (m, 7H)

<Step 2> Synthesis of A-11

2-(3-(2-(3-chlorobenzoyl)phenyl)triaz-2-en-1-yl)acetonitrile (2.98 g, 10 mmol) obtained in step 1 was dissolved in chloroform (200ml) and then dried. Neutral alumina (30.58 g, 0.3 mol) was added and stirred at room temperature for 2 days. After completion of the reaction, the organic layer was concentrated and recrystallized after washing with chloroform several times to obtain the target compound, A-11 (1.54 g, yield 55%).

¹ H-NMR: δ 7.52 (m, 3H), 7.77 (m, 4H), 7.97 (s, 1H), 8.13 (d, 1H)

[ Preparation example 12] Synthesis of A-12

<Step 1> 3-phenyl- [1,2,3]triazolo[1,5-a]pyridine -6- Amin's synthesis

[Preparation] except that (5-aminopyridin-2-yl)(phenyl)methanone (1.98 g, 10 mmol) was used as a reactant instead of 1-(6-chloropyridin-2-yl)ethan-1-one. The same process as in Example 1 was performed to obtain the target compound 3-phenyl-[1,2,3]triazolo[1,5-a]pyridin-6-amine (1.13 g, yield 54%).

¹ H-NMR: δ 6.72 (s, 1H), 7.15 (d, 1H), 7.48 (m, 4H), 7.84 (m, 2H), 8.53 (s, 1H)

<Step 2> N-(2- bromophenyl )-3-phenyl- [1,2,3]triazolo[1,5-a]pyridine -6- Amin's synthesis

3-phenyl-[1,2,3]triazolo[1,5-a]pyridin-6-amine (2.10 g, 10 mmol), 1,2-dibromobenzene (2.35 g, 10 mmol), Pd(OAc) ₂ (0.11 g, 5 mol%), P(t-Bu) ₃ (0.20 g, 1 mmol), NaO(t-Bu) (1.92 g, 20 mmol), toluene (200 ml) was mixed and stirred at 110°C for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, the target compound, N-(2-bromophenyl)-3-phenyl-[1,2,3]triazolo[1,5-a]pyridine-6-, was obtained using column chromatography. Amine (1.93 g, yield 53%) was obtained.

¹ H-NMR: δ 7.07 (m, 4H), 7.50 (m, 4H), 7.66 (d, 1H), 7.84 (m, 2H), 8.53 (s, 1H), 9.23 (s, 1H)

<Step 3> Synthesis of A-12

N-(2-bromophenyl)-3-phenyl-[1,2,3]triazolo[1,5-a]pyridin-6-amine (3.65 g, 10 mmol) obtained in step 2 under nitrogen stream, Pd(PPh ₃ ) ₂ Cl ₂ (1.40 g, 20 mol%), NaOAc.3H ₂ O (3.4 g, 25 mmol), and DMA (150 ml) were mixed and stirred at 130°C for 16 hours. After completion of the reaction, it was concentrated and purified by column chromatography to obtain the target compound, A-12 (1.42 g, yield 50%).

¹ H-NMR: δ 7.23 (t, 1H), 7.55 (m, 2H), 7.84 (m, 2H), 7.97 (d, 1H), 8.10 (d, 1H), 11.71 (s, 1H)

[ Preparation example 13] Synthesis of A-13

<Step 1> 6- fluoro -3-phenyl- [1,2,3]triazolo[1,5-a]pyridine synthesis

[ The same process as in Preparation Example 1 was performed to obtain the target compound 6-fluoro-3-phenyl-[1,2,3]triazolo[1,5-a]pyridine (1.04 g, yield 49%).

¹ H-NMR: δ 7.36 (d, 1H), 7.50 (m, 4H), 7.84 (m, 2H), 8.30 (s, 1H)

<Step 2> 6-(2- bromo -4- Chlorophenoxy )-3-phenyl- [1,2,3]triazolo[1,5-a]pyridine synthesis

6-Fluoro-3-phenyl-[1,2,3]triazolo[1,5-a]pyridine (2.13 g, 10 mmol), 2-bromo-4-chlorophenol obtained in step 1 under nitrogen stream. (2.07 g, 10 mmol), K ₂ CO ₃ (2.76 g, 20 mmol), and NMP (150 ml) were mixed and stirred at 220°C for 12 hours. After completion of the reaction, it was concentrated and purified by column chromatography to obtain the target compound, 6-(2-bromo-4-chlorophenoxy)-3-phenyl-[1,2,3]triazolo[1,5-a]pyridine. (1.92 g, yield 48%) was obtained.

¹ H-NMR: δ 6.64 (d, 1H), 7.16 (d, 1H), 7.34 (d, 1H), 7.55 (m, 5H), 7.84 (m, 2H), 8.56 (s, 1H)

<Step 3> Synthesis of A-13

6-(2-bromo-4-chlorophenoxy instead of N-(2-bromophenyl)-3-phenyl-[1,2,3]triazolo[1,5-a]pyridin-6-amine as reactant Si) Same process as <Step 3> of [Preparation Example 12] except that -3-phenyl-[1,2,3]triazolo[1,5-a]pyridine (4.00 g, 10 mmol) was used. was performed to obtain the target compound A-13 (1.50 g, yield 47%).

¹ H-NMR: δ 7.20 (d, 1H), 7.33 (d, 1H), 7.54 (m, 6H), 7.84 (m, 2H)

[ Preparation example 14] Synthesis of A-14

<Step 1> 6- bromo -3-(4- Chlorophenyl )- [1,2,3]triazolo[1,5-a]pyridine synthesis of

Except that (5-bromopyridin-2-yl)(4-chlorophenyl)methanone (2.96 g, 10 mmol) was used as a reactant instead of 1-(6-chloropyridin-2-yl)ethan-1-one. Then, the same process as [Preparation Example 1] was performed to obtain the target compound 6-bromo-3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridine (1.41 g, Yield 46%) was obtained.

¹ H-NMR: δ 7.52 (m, 2H), 7.72 (d, 1H), 7.98 (m, 2H), 8.18 (d, 1H), 8.79 (s, 1H)

<Step 2> 3-(4- Chlorophenyl )-6-(4,4,5,5- tetramethyl -1,3,2- Dioxaborolan -2-day)-[1,2,3]triazolo[1,5-a]pyridine synthesis

6-Bromo-3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridine (3.08 g, 10 mmol), 4,4, obtained in step 1 under nitrogen stream. 4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane) (2.53 g, 10 mmol), Pd(dppf) Cl ₂ (0.36 g, 5 mol%), KOAc (1.96 g, 20 mmol), and 1,4-dioxane (100 ml) were mixed and stirred at 100°C for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, the target compound, 3-(4-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxabororane, was purified using column chromatography. -2-day)-[1,2,3]triazolo[1,5-a]pyridine (1.60 g, yield 45%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 7.33 (d, 1H), 7.52 (m, 2H), 7.70 (d, 1H), 7.98 (m, 2H), 8.33 (s, 1H)

<Step 3> 2-(2-(3-(4- Chlorophenyl )- [1,2,3]triazolo[1,5-a]pyridine Synthesis of -6-yl)phenyl)propan-2-ol

3-(4-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-[1,2,3]triazolo[ 1,5-a]pyridine (3.55 g, 10 mmol), 2-(2-bromophenyl)propane-2-ol (2.36 g, 11 mmol), K ₂ CO ₃ (2.07 g, 15 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 0.5 mmol), toluene (60 mL), and purified water (15 ml) were mixed and stirred at 110°C for 12 hours. After cooling to room temperature, H ₂ O was added and extraction was performed using brine. After removing moisture with Na ₂ SO ₄ , the organic layer was concentrated and subjected to column chromatography to obtain 2-(2-(3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a ]Pyridin-6-yl)phenyl)propan-2-ol (1.60 g, 44%) was obtained.

¹ H-NMR: δ 1.35 (s, 6H), 5.50 (s, 1H), 7.40 (m, 6H), 7.80 (d, 1H), 7.98 (m, 2H), 8.42 (d, 1H), 8.93 ( s, 1H)

<Step 4> Synthesis of A-14

Cool the temperature to 0℃ and add 2-(2-(3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridin-6-yl)phenyl)propane in 1L of toluene. After -2-ol (36.38 g, 0.1 mol) was added, methanesulfonic acid (6.5 ml, 10 mmol) was added dropwise. After raising the temperature to room temperature, 100 ml of purified water was added to terminate the reaction. After extracting the mixed solution with CH ₂ Cl ₂ , the separated organic layer was neutralized with 7 ml of saturated calcium carbonate and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound, A-14 (14.87 g, yield 43%).

¹ H-NMR: δ 1.75 (s, 6H), 7.39 (m, 3H), 7.52 (m, 2H), 7.65 (d, 1H), 7.76 (d, 1H), 8.00 (m, 3H)

[ Synthesis example 1] Synthesis of J-1

A-1 (1.67 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabororane- 2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(OAc) ₂ (0.11 g, 5 mol%), Xphos (0.47 g, 2 mmol), Cs ₂ CO ₃ (6.51 g, 20 mmol) and toluene/EtOH/H ₂ O (80 ml/40 ml/20 ml) were mixed and stirred at 110°C for 6 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, J-1 (1.85 g, yield 42%), was obtained using column chromatography.

[LCMS]: 440

[ Synthesis example 2] Synthesis of J-2

A-2 (2.29 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-) instead of loran-2-yl)phenyl)-1,3,5-triazine Synthesis example except using dioxabororan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (5.11 g, 10.0 mmol) The same process as 1 was performed to obtain the target compound, J-2 (2.37 g, yield 41%).

[LCMS]: 578

[ Synthesis example 3] Synthesis of J-3

A-3 (2.29 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Loran-2-yl) phenyl) -1,3,5-triazine instead of 10-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxabororane- 2-yl)-10H-spiro[acridine-9,9'-fluorene] (5.33 g, 10.0 mmol) was performed in the same manner as in Synthesis Example 1 to produce the target compound, J-3. (2.40 g, yield 40%) was obtained.

[LCMS]: 600

[ Synthesis example 4] Synthesis of J-4

A-4 (2.30 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor loran-2-yl)phenyl)-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4-yl)-4-(4-fluorophenyl)-6-( Synthesis example except using 4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl)pyrimidine (5.28 g, 10.0 mmol) The same process as 1 was performed to obtain the target compound, J-4 (2.44 g, yield 41%).

[LCMS]: 596

[ Synthesis example 5] Synthesis of J-5

A-5 (2.03 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Loran-2-yl)phenyl)-1,3,5-triazine instead of 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1 The target compound, J-5 (2.09 g, yield 42%), was obtained by performing the same procedure as in Synthesis Example 1 except for using 3,2-dioxabororane (4.58 g, 10.0 mmol).

[LCMS]: 499

[ Synthesis example 6] Synthesis of J-6

A-6 (2.03 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor loran-2-yl)phenyl)-1,3,5-triazine instead of 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine (5.10 g, 10.0 mmol) was used, and the same process as Synthesis Example 1 was performed. The target compound, J-6 (2.69 g, yield 43%) was obtained.

[LCMS]: 627

[ Synthesis example 7] Synthesis of J-7

A-7 (2.79 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Synthesis except that (3-(triphenylen-2-yl)phenyl)boronic acid (3.48 g, 10.0 mmol) was used instead of loran-2-yl)phenyl)-1,3,5-triazine. The same process as Example 1 was performed to obtain the target compound, J-7 (2.40 g, yield 44%).

[LCMS]: 547

[ Synthesis example 8] Synthesis of J-8

A-8 (3.29 g, 10 mmol), 9-phenyl-9H,9'H-3,3'-bicarbazole (4.08 g, 10 mmol), Pd(OAc) ₂ (0.11 g, 5) under nitrogen stream. mol%), P(t-Bu) ₃ (0.20 g, 1 mmol), NaO(t-Bu) (1.92 g, 20 mmol), and toluene (200 ml) were mixed and stirred at 110°C for 12 hours. . After completion of the reaction, extraction was performed with methylene chloride, then MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, the target compound, J-8 (3.15 g, yield 45%) was obtained using column chromatography.

[LCMS]: 701

[ Synthesis example 9] Synthesis of J-9

A-9 (2.77 g, 10.0 mmol) was used instead of A-8, and N-([1,1'-biphenyl]-4 was used instead of 9-phenyl-9H,9'H-3,3'-bicarbazole. -1)-9,9-dimethyl-9H-fluoren-2-amine (3.61 g, 10.0 mmol) was performed in the same manner as in Synthesis Example 8, except for using the target compound, J-9 (2.77 g). , yield 46%) was obtained.

[LCMS]: 602

[ Synthesis example 10] Synthesis of J-10

A-10 (4.20 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Same as Synthesis Example 1 except that (4-(diphenylamino)phenyl)boronic acid (5.78 g, 20.0 mmol) was used instead of loran-2-yl)phenyl)-1,3,5-triazine. The process was performed to obtain the target compound, J-10 (3.08 g, yield 47%).

[LCMS]: 655

[ Synthesis example 11] Synthesis of J-11

A-11 (2.80 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Synthesis except that (9-phenyl-9H-carbazol-3-yl)boronic acid (2.87 g, 10.0 mmol) is used instead of loran-2-yl)phenyl)-1,3,5-triazine. The same process as Example 1 was performed to obtain the target compound, J-11 (2.34 g, yield 48%).

[LCMS]: 457

[ Synthesis example 12] Synthesis of J-12

A-12 (2.84 g, 10.0 mmol) was used instead of A-8, and instead of 9-phenyl-9H,9'H-3,3'-bicarbazole, (4-bromophenyl)diphenylphosphine oxide (3.57 g, 10.0 mmol), the same process as Synthesis Example 8 was performed to obtain the target compound, J-12 (2.74 g, yield 49%).

[LCMS]: 560

[ Synthesis example 13] Synthesis of J-13

A-13 (3.19 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor 4-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2 instead of loran-2-yl)phenyl)-1,3,5-triazine -1) The same procedure as in Synthesis Example 1 was performed except for using quinazoline (3.32 g, 10.0 mmol) to obtain the target compound, J-13 (2.44 g, yield 50%).

[LCMS]: 489

[ Synthesis example 14] Synthesis of J-14

A-14 (3.45 g, 10.0 mmol) was used instead of A-1 and 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabor Instead of loran-2-yl)phenyl)-1,3,5-triazine, 2-(9,9'-spirobi[fluoren]-3-yl)-4,4,5,5-tetramethyl- The target compound, J-14 (3.19 g, yield 51%), was obtained by performing the same process as Synthesis Example 1 except for using 1,3,2-dioxabororane (4.42 g, 10.0 mmol). .

[LCMS]: 625

[ Example 1 to 7] blue organic electric field Fabrication of light emitting devices

Compounds J-1 to 7 synthesized in the synthesis example were purified by 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 a 1500 Å thin film of ITO (indium tin oxide) 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)/compound J-1 to 7, respectively. An organic electroluminescent device was manufactured by stacking compounds (30 nm)/LiF (1 nm)/Al (200 nm) in that order.

[ Comparative example 1] Blue Organic electric field Fabrication of light emitting devices

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

[ Comparative example 2]Blue abandonment electric field Fabrication of light emitting devices

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

The structures of NPB, AND, and Alq3 used in Examples 1 to 7 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example One]

For the blue organic electroluminescent devices manufactured in Examples 1 to 7 and Comparative Examples 1 and 2, the driving voltage, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. indicated.

Sample electron transport layer driving voltage
(V) Luminescence peak
(nm) Current efficiency
(cd/A) Example 1 J-1 3.7 451 7.4 Example 2 J-2 4.1 452 8.1 Example 3 J-3 3.5 453 7.7 Example 4 J-4 3.2 452 8.1 Example 5 J-5 3.7 451 8.1 Example 6 J-6 4.0 452 7.7 Example 7 J-7 3.8 454 8.3 Comparative Example 1 Alq ₃ 5.4 458 5.5 Comparative Example 2 - 4.9 460 5.8

As shown in Table 1, the blue organic electroluminescent device using the compound of the present invention in the electron transport layer (Examples 1 to 7) is the same as the blue organic electroluminescent device using the conventional Alq ₃ in the electron transport layer (Comparative Example 1) and It was found that it exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device without an electron transport layer (Comparative Example 2).

[ Example 8 to 14] blue organic electric field Fabrication of light emitting devices

Compounds J-8 to 14 synthesized in the synthesis example were purified by high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) 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. and transferred the substrate 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)/ Compound J-8~14 (5 An organic electroluminescent device was manufactured by stacking in the following order: nm)/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm).

[ Comparative example 3] Blue Organic electric field Manufacturing of light emitting devices

A blue organic electroluminescent device was produced in the same manner as Example 8, except that Compound J-8 was not used as the electron transport auxiliary layer material and Alq ₃ , the electron transport layer material, was deposited at 30 nm instead of 25 nm. Produced.

[ Evaluation example 2]

For the organic electroluminescent devices manufactured in Examples 8 to 14 and Comparative Example 3, the driving voltage, emission wavelength, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below.

Sample Electron transport auxiliary layer Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 8 J-8 4.5 455 8.6 Example 9 J-9 3.4 452 8.4 Example 10 J-10 3.8 453 9.0 Example 11 J-11 3.9 454 8.1 Example 12 J-12 3.7 457 7.8 Example 13 J-13 3.8 457 8.4 Example 14 J-14 3.6 452 8.7 Comparative Example 3 - 4.8 458 6.0

As shown in Table 2, the blue organic electroluminescent device using the compound of the present invention in the electron transport auxiliary layer (Examples 8 to 14) is better than the blue organic electroluminescent device without the electron transport auxiliary layer (Comparative Example 3). It was found to exhibit excellent performance in terms of current efficiency, luminescence peak, 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 (15)

The following compounds are represented by the following formula 3 or 4:
[Formula 3]

[Formula 4]

In Formulas 3 and 4 above,
R ₁ and R ₄ to R ₇ are each independently a substituent represented by the following formula (2);
[Formula 2]

In Formula 2,
* refers to the part where the combination takes place;
L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
A plurality of R ₃ is the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkyl group. Nyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyl group. Period, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ aryl sulfo Nyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ It is selected from the group consisting of C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and C ₆ ~ C ₆₀ arylamine group, or is bonded to an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, the number of nuclear atoms Forming a non-aromatic condensed polycycle of 5 to 50 nuclear atoms, an aromatic hetero ring of 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle of 5 to 50 nuclear atoms;
At least one of the plurality of R ₃ is each independently a C ₂ to C ₄₀ alkenyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group with 5 to 60 nuclear atoms, or a C ₃ to C ₄₀ alkylsilyl group. , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group , C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group,
The arylene group and heteroarylene group of L ₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R ₃ , Alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group, and two adjacent R The aromatic ring, non-aromatic condensed polycyclic ring, aromatic hetero ring and non-aromatic condensed hetero polycyclic ring formed by combining ₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylcarbonyl group and C ₆ ~ C ₆₀ arylsilyl group, and when substituted with a plurality of substituents, they are the same or different from each other.
delete According to paragraph 1,
One or more of R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R _{7 , and R 7 and} R ₁ are combined to form an aromatic ring having 5 to 50 nuclear atoms or a non-ring having 5 to 50 nuclear atoms. Forming an aromatic condensed polycycle, an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle having 5 to 50 nuclear atoms;
The aromatic ring, non-aromatic condensed polycycle, aromatic heterocycle and non-aromatic condensed heteropolycyclic ring formed by combining R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and R ₁ are each Independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, number of nuclear atoms 5 to 60 heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₁ to C ₄₀ alkylsulfonyl group, C ₆ to C ₆₀ arylsulfonyl group, C ₆ ~C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ aryl A compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of a carbonyl group and a C ₆ to C ₆₀ arylsilyl group, and when substituted with a plurality of substituents, they are the same or different from each other. According to paragraph 1,
A compound in which one or more of R ₄ and R ₅ , R ₅ and R ₆ , and R ₆ and R ₇ each independently form a condensed ring with a ring represented by any one of the following formulas 5 to 9:
[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 5 to 9,
The dotted line indicates the part where condensation takes place;
Y ₁ to Y ₄ are each independently N or C(Ar ₁ ), and when there are multiple Ar _1s , they are the same or different from each other;
X ₅ is O, N, C(Ar ₂ )(Ar ₃ ), S or Si(Ar ₄ )(Ar ₅ );
Ar ₁ to Ar ₅ and R ₈ to R ₁₃ are each independently a substituent represented by the following formula (10);
[Formula 10]

In Formula 10 above,
* refers to the part where the combination takes place;
L ₂ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;
The alkyl group, _alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other. According to paragraph 4,
The ring represented by Formula 5 is a compound represented by Formula 11 or 12 below:
[Formula 11]

[Formula 12]

In Formulas 11 and 12 above,
The dotted line indicates the part where condensation takes place;
R ₁₅ to R ₁₈ are each independently a substituent represented by the following formula (13);
[Formula 13]

In Formula 13 above,
* refers to the part where the combination takes place;
L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;
The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other. According to paragraph 4,
The ring represented by Formula 6 is a compound represented by Formula 14 below:
[Formula 14]

In Formula 14 above,
The dotted line indicates the part where condensation takes place;
R ₂₀ to R ₂₄ are each independently a substituent represented by the following formula (13);
[Formula 13]

In Formula 13 above,
* refers to the part where the combination takes place;
L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;
The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other. According to paragraph 4,
The ring represented by Formula 7 is a compound represented by Formula 15 or 16 below:
[Formula 15]

[Formula 16]

In Formulas 15 and 16 above,
The dotted line indicates the part where condensation takes place;
R ₂₅ to R ₃₆ are each independently a substituent represented by the following formula (13);
[Formula 13]

In Formula 13 above,
* refers to the part where the combination takes place;
L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;
The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, They may be the same or different from each other;
X ₅ is as defined in paragraph 4. According to paragraph 1,
The compound represented by Formula 4 is a compound represented by Formula 17 or 18 below:
[Formula 17]

[Formula 18]

In Formulas 17 and 18 above,
B ₁ and B ₂ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, or a heteroaryl group with 5 to 60 nuclear atoms, or are combined with each other to form an aromatic ring with 5 to 50 nuclear atoms. , forming a non-aromatic condensed polycycle with 5 to 50 nuclear atoms, an aromatic hetero ring with 5 to 50 nuclear atoms, or a non-aromatic condensed hetero polycycle with 5 to 50 nuclear atoms;
The aromatic ring, non-aromatic condensed polycycle, aromatic hetero ring and non-aromatic condensed hetero polycycle formed by combining the alkyl group, aryl group and heteroaryl group of B ₁ and B ₂ and B ₁ and B ₂ are each independently deuterium. , halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ to C ₆₀ arylsilyl groups, and when substituted with a plurality of substituents, they may be the same or different from each other;
A ₁ to A ₉ are each independently a substituent represented by the following formula (19);
[Formula 19]

In Formula 19 above,
* refers to the part where the combination takes place;
L ₄ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
R ₃₇ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear 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 alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group , C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C It is selected from the group consisting of an arylcarbonyl group of ₆₀ and an arylamine group of C ₆ to C ₆₀ , or is combined with an adjacent group to form an aromatic ring with 5 to 50 nuclear atoms, a non-aromatic condensed polycyclic ring with 5 to 50 nuclear atoms, and a nucleus. forming an aromatic hetero ring having 5 to 50 nuclear atoms, or a non-aromatic condensed heteropolycyclic ring having 5 to 50 nuclear atoms;
The _alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, An aromatic ring, non-aromatic, formed by combining an alkyl boron group, an aryl boron group, an aryl phosphanyl group, a mono or diaryl phosphinyl group, an alkyl carbonyl group, an aryl carbonyl group and an aryl silyl group, and two adjacent substituents bonded to each other. Condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heteropolycyclic rings each independently contain deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₆ to C ₆₀ aryl group, 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 alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ When unsubstituted or substituted with one or more substituents selected from the group consisting of ~C ₄₀ alkylcarbonyl group, C ₆ ~C ₆₀ arylcarbonyl group, and C ₆ ~C ₆₀ arylsilyl group, and substituted with a plurality of substituents, These may be the same or different from each other. According to paragraph 1,
The compound wherein L ₁ is selected from the group consisting of a phenylene group, a biphenylene group, a naphthalenyl group, a quinazolinyl group, and a carbazolyl group. According to paragraph 1,
The compound wherein L ₁ is a linker represented by any one of the following formulas A-1 to A-6:

In the above formulas A-1 to A-6,
* refers to the part where the combination takes place;
q is an integer from 0 to 4;
A ₁₀ is 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, nuclear atom Heterocycloalkyl group with 3 to 40 atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ selected from the group consisting of an arylcarbonyl group and an arylamine group having C ₆ to C ₆₀ , and when there are more than one A ₁₀ , they are the same or different from each other;
Z ₁ to Z ₈ are each independently N or C(Ar ₆ );
In Formula A-3, any one of Z ₁ to Z ₄ and any one of Z ₅ to Z ₈ that is bonded as a linker is C(Ar ₆ ), wherein Ar ₆ is absent;
In Formula A-4, any two of Z ₁ to Z ₄ bonded as a linker are C(Ar ₆ ), and Ar ₆ is absent;
X ₆ is each independently O, S, N(Ar ₇ ) or C(Ar ₈ )(Ar ₉ );
X ₇ is N or C(Ar ₁₀ );
Ar ₆ to Ar ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkyl carbo selected from the group consisting of a nyl group, an arylcarbonyl group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , and when there is a plurality of Ar ₆ , they are the same or different from each other;
A ₁₀ and Ar ₆ to Ar ₁₀ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl sulfo Nyl group, arylsulfonyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, aryl carbonyl group, and aryl silyl group are each independently a deuterium, halogen, cyano, or nitro group. , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ Arylphosphanyl group of C ₆₀ , mono or diarylphosphinyl group of C ₆ ~ C ₆₀ , alkylcarbonyl group of C ₁ ~ C ₄₀ , arylcarbonyl group of C ₆ ~ C ₆₀ and arylsilyl of C ₆ ~ C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of groups, and when substituted with a plurality of substituents, these may be the same or different from each other. delete According to paragraph 1,
A compound wherein at least one of R ₁ and R ₃ is each independently a substituent represented by any one of the following formulas B-1 to B-7:

In the above formulas B-1 to B-7,
Z ₉ to Z ₁₃ are each independently N or C(B ₄ );
In Formula B-4, any one of Z ₉ to Z ₁₂ bonded as a substituent is C(Ar ₁₁ ), and in this case, Ar ₁₁ is absent;
T ₁ and T ₂ are each independently a single bond, C(Ar ₁₂ )(Ar ₁₃ ), N(Ar ₁₄ ), O, S, S(=O)(=0), B(Ar ₁₅ ), and Si( Ar ₁₆ )(Ar ₁₇ ), but both T ₁ and T ₂ are not single bonds;
T ₃ is N(Ar ₁₈ ) or O;
r and s are each independently integers from 0 to 4;
A ₁₁ and A ₁₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, selected from the group consisting of an arylcarbonyl group of C ₆ to C ₆₀ and an arylamine group of C ₆ to C ₆₀ , and when each of A ₁₁ and A ₁₂ is plural, they are the same or different from each other;
B ₃ , B ₄ and Ar ₁₁ to Ar ₁₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ aryl Sulfonyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ is selected from the group consisting of an alkylcarbonyl group of ~C ₄₀ , an arylcarbonyl group of _C6 ~ _C60 , and an arylamine group of _C6 ~ _C60 , and when there are multiple B ₄ and Ar ₁₁ to Ar ₁₈ , they are each other. identical or different;
A ₁₁ , A ₁₂ , B ₃ , B ₄ and Ar ₁₁ to Ar ₁₈ alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and arylsilyl group are each independently deuterium. , halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ arylsulfonyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, C ₁ ~ C ₄₀ alkylcarbonyl group, C ₆ ~ C ₆₀ arylcarbonyl group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆ to C ₆₀ arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other. 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 material layers interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic layers contains the compound according to claim 1. According to clause 14,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a lifespan improvement layer, a light emitting layer, and a light emitting auxiliary layer.