WO2018186551A1 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to a novel compound, and an organic electroluminescent element comprising the same. The compound according to the present invention is used in an organic layer of an organic electroluminescent element and, preferably, in a light emitting layer, thereby enabling the luminous efficiency, driving voltage, lifespan, and the like of the organic electroluminescent element to improve.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

From the observation of Bernanose's organic thin film emission in the 1950s, research on organic electroluminescent (EL) devices led to blue electroluminescence using anthracene single crystals in 1965, followed by Tang in 1987 The organic electroluminescent device of the laminated structure divided into the functional layer of a positive hole layer and a light emitting layer was proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

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

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

To date, NPB, BCP, Alq ₃ and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials. Particularly, 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 the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.

However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, the development of the organic material layer material which is excellent in performance is calculated | required.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent holes, electron injection and transport ability, light emitting ability and the like.

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

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

[Formula 1]

[Formula 2]

In Chemical Formula 1 and Chemical Formula 2,

At least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ is condensed with a ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where condensation takes place;

l, m, n and p are each independently an integer from 0 to 4;

R _1, R ₂ and Ar ₁ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, A C ₆ -C ₆₀ arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

A ₁ to A ₄ and R ₃ to R ₆ which do not form a condensed ring with the ring represented by Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl group and C ₆ to C ₆₀ arylamine Selected from the group consisting of groups, and when there are a plurality of R ₃ to R ₆ , they are the same as or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyl jade of A ₁ to A ₄ , R ₁ to R ₆ and Ar ₁ which do not form a condensed ring with the ring represented by Formula 2 above The period, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group , Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 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, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ An aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, C ₆ ~ C ₆₀ Mono Or when substituted or unsubstituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , and substituted with a plurality of substituents, they are the same or different from each other.

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

"Halogen" in the present invention means fluorine, chlorine, bromine or iodine.

"Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted 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 in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

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

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

“Heterocycloalkyl” in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.

“Condensed ring” in the present invention 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 transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifespan, and efficiency are greatly improved.

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

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

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

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

[Formula 1]

[Formula 2]

In Chemical Formula 1 and Chemical Formula 2,

At least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ is condensed with a ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where condensation takes place;

l, m, n and p are each independently an integer from 0 to 4;

R _1, R ₂ and Ar ₁ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, A C ₆ -C ₆₀ arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

A ₁ to A ₄ and R ₃ to R ₆ which do not form a condensed ring with the ring represented by Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl group and C ₆ to C ₆₀ arylamine Selected from the group consisting of groups, and when there are a plurality of R ₃ to R ₆ , they are the same as or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyl jade of A ₁ to A ₄ , R ₁ to R ₆ and Ar ₁ which do not form a condensed ring with the ring represented by Formula 2 above The period, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group , Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 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, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ An aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, C ₆ ~ C ₆₀ Mono Or when substituted or unsubstituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , and substituted with a plurality of substituents, they are the same as or different from each other.

Hereinafter, the present invention will be described in detail.

One. New organic compounds

The novel compounds of the present invention can be represented by the following formula (1):

[Formula 1]

[Formula 2]

In Chemical Formula 1 and Chemical Formula 2,

At least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ is condensed with a ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where condensation takes place;

l, m, n and p are each independently an integer from 0 to 4;

R _1, R ₂ and Ar ₁ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, A C ₆ -C ₆₀ arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

A ₁ to A ₄ and R ₃ to R ₆ which do not form a condensed ring with the ring represented by Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl group and C ₆ to C ₆₀ arylamine Selected from the group consisting of groups, and when there are a plurality of R ₃ to R ₆ , they are the same as or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyl jade of A ₁ to A ₄ , R ₁ to R ₆ and Ar ₁ which do not form a condensed ring with the ring represented by Formula 2 above The period, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group , Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 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, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ An aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, C ₆ ~ C ₆₀ Mono Or when substituted or unsubstituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , and substituted with a plurality of substituents, they are the same or different from each other.

In the present invention, the compound represented by Chemical Formula 1 is a host material containing a spirocarbazole-based moiety, and has excellent electrochemical stability, high glass transition temperature and carrier transport ability, and particularly electron and hole transport mobility. This is so excellent that the balance of carriers in the light emitting layer exhibits very good characteristics. The materials represented by Chemical Formula 1 are structurally characterized by combining a core core and an electron-withdrawing group (EWG), and are particularly excellent in electron mobility and excellent in high glass transition temperature and thermal stability. In addition, the holes and electrons transferred to the light emitting layer have excellent charge balance in materials having the structure of Formula 1, so that the exciton is generated, and thus the light emission efficiency of the device can be improved due to high energy transfer to the dopant, and the durability and stability of the device are improved. The lifetime of the device can thus be efficiently increased. Most of the materials developed show physical features that enable low voltage operation and thus improve their lifetime.

For this reason, the compound represented by Formula 1, which is a representative claim structure of the present invention, has excellent light emission characteristics, and thus, any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device. Can be used as a material. Preferably it can be used as a material of the light emitting layer of green phosphorescence and red phosphorescence.

In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent green n-type host or a phosphorescent red host, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer life than a conventional light emitting host material can be manufactured. In addition, it is possible to manufacture a full color display panel with improved efficiency and long life.

Preferably, it may be used as a material of any one of an electron transport auxiliary layer further laminated on the green phosphorescent light emitting layer, the electron transport layer, and the electron transport layer. In addition, since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.

In addition, the exciton generated in the light emitting layer can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.

According to one preferred embodiment of the present invention, the compound may be a compound represented by any one of the following Formulas 3 to 8:

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 3 to 8.

R ₁ to R _6, A ₁ to A ₄ , l, m, n, p and Ar ₁ are as defined in claim ₁ .

According to a preferred embodiment of the present invention, R ₁ and R ₂ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms Selected,

The alkyl group, aryl group and heteroaryl group of R ₁ and R ₂ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ and R ₂ are each independently composed of a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group Selected from the military,

The methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group of R ₁ and R ₂ are each independently C ₁ ~ C ₄₀ alkyl group, C ₆ ~ When substituted or unsubstituted with one or more substituents selected from the group consisting of a C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ and R ₂ are each independently composed of a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group Selected from the military,

The methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups of R ₁ and R ₂ are each independently a methyl, ethyl, propyl, butyl or pen When substituted or unsubstituted with one or more substituents selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, and substituted with a plurality of substituents, they are the same as or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ may be a compound represented by the following formula (9):

[Formula 9]

In Chemical Formula 9,

* Means the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

R ₇ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

Wherein L ₁ and the arylene group and a heteroarylene group, an alkyl group of the R ₇ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other.

According to one preferred embodiment of the present invention, L ₁ and L ₂ may be each independently a direct bond or a linker selected from the group consisting of Formulas A-1 to A-4, more preferably a direct bond It may be a linker represented by A-1 or A-2:

In Chemical Formulas A-1 to A-4,

* Means the part where the coupling is made.

According to a preferred embodiment of the present invention, R ₇ is selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group,

The alkyl group, aryl group and heteroaryl group of R ₇ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When unsubstituted or substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₇ is a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolo Selected from the group consisting of pyridinyl, quinolinyl, isoquinolinyl, cynolinyl, quinoxalinyl and quinazolinyl;

Methyl groups of the R _7, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, pyrimidinyl group, triazinyl group, a naphthyl Frontale group, triazolo pyridinyl group, quinolinyl group, isoquinolinyl Nolinyl group, cynolinyl group, quinoxalinyl group and quinazolinyl group are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₇ is a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolo Selected from the group consisting of pyridinyl, quinolinyl, isoquinolinyl, cynolinyl, quinoxalinyl and quinazolinyl;

Methyl groups of the R _7, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, pyrimidinyl group, triazinyl group, a naphthyl Frontale group, triazolo pyridinyl group, quinolinyl group, isoquinolinyl Nolinyl group, cynolinyl group, quinoxalinyl group and quinazolinyl group are each independently a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthaleyl group Substituted or unsubstituted with one or more substituents selected from the group consisting of a nil group, a triazolopyridinyl group, a quinolinyl group, an isoquinolinyl group, a cynolinyl group, a quinoxalinyl group, and a quinazolinyl group, and a plural substituent group In this case, they are the same or different from each other.

According to one preferred embodiment of the present invention, R ₇ may be a substituent represented by any one of the following Formulas 10 to 12:

[Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 10 to 12,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₉ );

q is an integer from 0 to 4;

R ₈ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Or a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring, and when R ₈ is a plurality, Same or different from each other;

R ₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Or a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring, and when R ₉ is a plurality, Same or different from each other;

Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R ₈ and R ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 10 may be a substituent represented by the following formula (13):

[Formula 13]

In Chemical Formula 13,

* Means the part where the bond is made;

R ₁₀ and R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, it said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of;

Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₁₀ and R ₁₁ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other;

Z ₁ , Z ₃ and Z ₅ are as defined in the formula (10).

According to one preferred embodiment of the present invention, the substituent represented by Formula 10 may be a substituent represented by any one of the following formulas B-1 to B-3:

In Chemical Formulas B-1 to B-3,

* Means the part where the coupling is made,

R ₁₀ and R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₁₀ and R ₁₁ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents and substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ and R ₁₁ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms Selected;

The alkyl group, aryl group and heteroaryl group of R ₁₀ and R ₁₁ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.

According to one preferred embodiment of the present invention, R ₁₀ and R ₁₁ may be independently selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₁₀ and R ₁₁ are each independently C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and nuclear atom When substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ and R ₁₁ may be each independently selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group, and more Preferably it may be selected from the group consisting of phenyl group, biphenyl group and pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₁₀ and R ₁₁ are each independently a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, a phenyl group and a biphenyl group When substituted or unsubstituted with one or more substituents selected from the group consisting of, and substituted with a plurality of substituents, they are the same or different from each other.

According to one preferred embodiment of the present invention, the substituent represented by Formula 11 may be a substituent represented by the following Formula 14:

[Formula 14]

In Chemical Formula 14,

* Means the part where the coupling is made,

q, R ₈ and R ₉ are as defined in Chemical Formula 11 above.

According to a preferred embodiment of the present invention, R ₉ is selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;

The alkyl group, aryl group and heteroaryl group of R ₉ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When unsubstituted or substituted with a plurality of substituents, they are the same as or different from each other.

According to one preferred embodiment of the present invention, R ₉ may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₉ are each independently C ₁ -C ₄₀ alkyl group, C ₆ -C ₆₀ aryl group and nuclear atom 5 to When unsubstituted or substituted with one or more substituents selected from the group consisting of 60 heteroaryl groups, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group, more preferably phenyl group, non It may be selected from the group consisting of a phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₉ are each independently a group consisting of methyl group, ethyl group, butyl group, propanyl group, pentyl group, phenyl group and biphenyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 12 may be a substituent represented by the following Formula 15:

[Formula 15]

In Chemical Formula 15,

* Means the part where the coupling is made,

q and R ₈ are the same as defined in Chemical Formula 12.

According to one preferred embodiment of the present invention, R ₈ is selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;

The alkyl group, aryl group and heteroaryl group of R ₈ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When unsubstituted or substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₈ may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₈ are each independently C ₁ -C ₄₀ alkyl group, C ₆ -C ₆₀ aryl group and nuclear atom number 5 to When unsubstituted or substituted with one or more substituents selected from the group consisting of 60 heteroaryl groups, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₈ may be selected from the group consisting of phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group, more preferably phenyl group, non It may be selected from the group consisting of a phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₈ are each independently a group consisting of methyl group, ethyl group, butyl group, propanyl group, pentyl group, phenyl group and biphenyl group When substituted or unsubstituted with one or more substituents selected from, and substituted with a plurality of substituents, they are the same or different from each other.

According to one preferred embodiment of the invention, the compound is 5 '-(4,6-diphenyl-1,3,5-triazin-2-yl) -10,10-dimethyl-5'H, 10H -Spiro [anthracene-9,11'-indeno [1,2-b] carbazole] or 11 '-(3- (4,6-diphenyl-1,3,5-triazin-2-yl) Phenyl) -10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole].

Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

[Revision under Rule 91 02.01.2018]

[Revision under Rule 91 02.01.2018]

[Revision under Rule 91 02.01.2018]

[Revision under Rule 91 02.01.2018]

[Revision under Rule 91 02.01.2018]

Compounds 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) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. abandonment Electric field  Light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or mixed two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.

The structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them. 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, the electron transport layer 34 and the cathode The electron injection layer 36 may be further included between the holes 20.

In the present invention, the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31. However, the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.

In addition, the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate the injection of electrons from the cathode to ultimately improve the power efficiency, commonly used in the art. As long as it can be used without particular limitation, for example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO and the like 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 emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30. The emission 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 life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling 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 thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. . Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.

In the present invention, the compound represented by Chemical Formula 1 includes a spirocarbazole-based moiety, which has excellent electrochemical stability, high glass transition temperature and carrier transport ability, and particularly electron and hole transport mobility. It is excellent in that the balance of carriers in the light emitting layer shows very good characteristics. The materials represented by Chemical Formula 1 are structurally characterized by combining a core core and an electron-withdrawing group (EWG), and are particularly excellent in electron mobility and excellent in high glass transition temperature and thermal stability. In addition, the holes and electrons transferred to the light emitting layer have excellent charge balance in materials having the structure of Formula 1, so that the exciton is generated, and thus the light emission efficiency of the device can be improved due to high energy transfer to the dopant, and the durability and stability of the device are improved. The lifetime of the device can thus be efficiently increased. Most of the materials developed show physical features that enable low voltage operation and thus improve their lifetime.

For this reason, the compound represented by Formula 1, which is a representative claim structure of the present invention, has excellent light emission characteristics, and thus, any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device. Can be used as a material. Preferably it can be used as a material of the light emitting layer of green phosphorescence and red phosphorescence.

Preferably, it may be used as a material of any one of an electron transport auxiliary layer further laminated on the green phosphorescent light emitting layer, the electron transport layer, and the electron transport layer. In addition, since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.

In addition, the exciton generated in the light emitting layer may be prevented from being diffused into the electron transport layer or the hole transport layer adjacent to the light emitting layer. The number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.

In addition, in the present invention, the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an 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 material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.

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

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

Further, the positive electrode material may be made of a high work function conductor, for example, 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), 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 may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following Examples are merely to illustrate the present invention, the present invention is not limited by the following Examples.

Example

[ Preparation  1] Core 1 of  synthesis

<Step 1> 2- (10,10- Dimethyl -10H- Spiro [Anthracene-9,9'- Fluorene ] -2'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] 30.0 g (0.076 mol), 4,4,4 ', 4', 5,5,5 ', 600 mL of dioxane was added to 25.2 g (0.099 mol) of 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane). 3.2 g (3.9 mmol) of Pd (dppf) Cl ₂ , 3.7 g (7.7 mmol) of XPhos, and 22.5 g (0.229 mol) of KOAc were added to the reaction solution. The mixture was heated to reflux at 130 for 5 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with EA 1.0 L 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 28.9 g (yield 78%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 7.92 (m, 3H), 7.60 (d, 2H), 7.34 (s, 1H), 7.30 (t, 1H), 7.18 (dt, 2H), 7.11 (t, 1H), 6.84 (m, 3H), 6.29 (dd, 2H), 1.92 (dd, 6H), 1.34 (s, 12H)

[LCMS]: 484

<Step 2> 10,10- Dimethyl -2 '-(2- Nitrophenyl ) -10H- Of spiro [anthracene-9,9'-fluorene]  synthesis

2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3, synthesized above To 28.0 g (57.8 mmol) of 2-dioxaborolane and 11.7 g (57.8 mmol) of 1-bromo-2-nitrobenzene were added 500 mL of dioxane and 200 mL of H ₂ O. 3.4 g (2.9 mmol) of Pd (PPh ₃ ) _{4 and} 24.0 g (173 mmol) of K ₂ CO ₃ were added thereto, and the resulting mixture was heated to reflux at 120 hours for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with EA 1.0 L 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 20.0 g (yield 72%) of the title compound.

1 H-NMR (in DMSO-d6): δ 8.07 (d, 1H), 8.02 (d, 1H), 7.82 (d, 1H), 7.68 (d, 2H), 7.61 (t, 1H), 7.50 (t, 1H), 7.35 (m, 3H), 7.18 (t, 3H), 6.87 (t, 2H), 6.80 (d, 1H), 6.71 (s, 1H), 6.14 (d, 2H), 1.81 (d, 6H )

[LCMS]: 479

<Step 3> Core One of  synthesis

20.0 g (41.7 mmol) of 10,10-dimethyl-2 '-(2-nitrophenyl) -10H-spiro [anthracene-9,9'-fluorene] synthesized above, 32.8 g of P (Ph) ₃ 300 mL of DCB was added to (125 mmol). The reaction solution was heated to reflux at 200 ° C. for 12 hours. 500 mL of purified water was added to terminate the reaction, extracted with EA 2.0 L, 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 9.7 g (yield 52%) of the title compound.

1 H-NMR (in DMSO-d6): δ 11.4 (s, 1H), 8.05 (d, 1H), 8.00 (s, 1H), 7.94 (d, 1H), 7.72 (d, 2H), 7.58 (s, 1H), 7.42 (d, 1H), 7.31 (m, 2H), 7.11 (m, 3H), 7.00 (t, 1H), 6.79 (m, 3H), 6.17 (d, 2H), 1.88 (d, 6H )

[LCMS]: 447

 [ Preparation  2] Core 2 of  synthesis

3.9 g (yield 21%) of the target compound, which is a structural isomer of Core 1, was obtained in the same manner as <Steps 1 to 3> of [Preparation Example 1].

1 H-NMR (in DMSO-d6): δ 9.4 (s, 1H), 8.30 (d, 1H), 8.12 (d, 1H), 7.94 (d, 1H), 7.90 (d, 1H), 7.78 (d, 2H), 7.36 (d, 1H), 7.29 (m, 4H), 7.13 (t, 1H), 7.00 (t, 1H), 6.78 (m, 3H), 6.21 (d, 2H), 2.11 (s, 3H ), 1.96 (s, 3H)

[LCMS]: 447

[ Preparation  3] Core 3 of  synthesis

<Step 1> 2- (10,10- Dimethyl -10H- Spiro [Anthracene-9,9'- Fluorene ] -3'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Except for using 3'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] as a reactant to the target compound in the same manner as in step 1 of [Preparation Example 1] 37.0 g (75% yield) were obtained.

¹ H-NMR (in CDCl ₃ ): δ 8.38 (s, 1H), 7.94 (d, 1H), 7.60 (m, 3H), 7.38 (t, 1H), 7.11 (m, 3H), 6.96 (t, 2H), 6.92 (t, 2H), 6.36 (d, 2H), 1.98 (s, 6H), 1.49 (s, 12H)

[LCMS]: 484

<Step 2> 10,10- Dimethyl -3 '-(2- Nitrophenyl ) -10H- Of spiro [anthracene-9,9'-fluorene]  synthesis

2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl-1,3, synthesized above Except for using 2-dioxaborolane, the same procedure as in Step 2 of [Preparation Example 1] was carried out to obtain 24.9 g (yield 68%) of the title compound.

1 H-NMR (in CDCl ₃ ): δ 11.7 (s, 1H), 8.90 (d, 1H), 8.78 (m, 3H), 8.35 (m, 1H), 7.87 (d, 1H), 7.70 (m, 4H ), 7.60 (d, 1H), 7.55 (d, 1H), 7.49 (t, 1H), 7.44 (dd, 1H), 1.82 (s, 6H)

[LCMS]: 479

<Step 3> Core 3 of  synthesis

Step 3 of [Preparation Example 1], except that 10,10-dimethyl-3 '-(2-nitrophenyl) -10H-spiro [anthracene-9,9'-fluorene] synthesized above was used. 9.2 g (yield 41%) of the title compound was obtained by the same procedure as the above.

[LCMS]: 447

[ Preparation  4] Synthesis of Core 4

8.8 g (yield 19%) of the target compound, which is a structural isomer of Core 3, was obtained in the same manner as <Steps 1 to 3> of [Preparation Example 2].

[LCMS]: 447

[ Preparation  5] Core 5 of  synthesis

<Step 1> 2- (10,10- Dimethyl -10H- Spiro [Anthracene-9,9'- Fluorene ] -4'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Except for using 4'-bromo-10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] as a reactant, the same procedure as in step 1 of [Preparation Example 1] was performed. 28.4 g (64% yield) of compound were obtained.

¹ H-NMR (in CDCl ₃ ): δ 8.76 (d, 2H), 7.92 (dd, 1H), 7.58 (dd, 2H), 7.27 (dt, 1H), 7.09 (m, 4H), 6.93 (dd, 1H), 6.79 (m, 3H), 6.26 (dd, 2H), 1.87 (dd, 6H), 1.48 (s, 12H)

[LCMS]: 484

<Step 2> 10,10- Dimethyl -4 '-(2- Nitrophenyl ) -10H- Of spiro [anthracene-9,9'-fluorene]  synthesis

2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl-1,3, synthesized above Except for using 2-dioxaborolane, the same procedure as in Step 2 of [Preparation Example 1] was carried out to obtain 16.4 g of the target compound (yield 59%).

[LCMS]: 479

<Step 3> Core 3 of  synthesis

Step 3 of [Preparation Example 1], except that 10,10-dimethyl-4 '-(2-nitrophenyl) -10H-spiro [anthracene-9,9'-fluorene] synthesized above was used. 7.9 g (yield 53%) of the title compound was obtained in the same manner as the same procedure.

[LCMS]: 447

[ Synthesis Example  1] Synthesis of Compound 1

100 mL of DMF was added to 5.0 g (11.2 mmol) of the compound of Preparation Example 1 and 3.0 g (13.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine. 0.67 g (16.8 mmol) of 60% NaH was added to the reaction solution. After stirring for 12 hours at room temperature 100 mL of purified water was added to terminate the reaction. The mixture was extracted with EA 300 mL and washed twice with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 4.8 g (yield 64%) of the title compound.

[LCMS]: 678

[ Synthesis Example  2] Synthesis of Compound 4

4.5 g (10.1 mmol) of the compound of Preparation Example 1 (Core 1) and 3.9 g (11.2 mmol of 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine 100 mL of toluene was added. 0.11 g (0.5 mmol) of Pd (OAc) ₂ , 0.40 g (1.1 mmol) of P (t-Bu) ₃ , and 1.8 g (10.0 mmol) of NaOt-Bu were added to the reaction solution and heated to reflux at 120 ° C. for 6 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 3.7 g (yield 55%) of the title compound.

[LCMS]: 716

[ Synthesis Example  3] Synthesis of Compound 6

Preparation Example 1 using 10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] and 2-chloro-4-phenylquinazoline Except that, the same procedure as in Synthesis Example 2 was performed to obtain 4.8 g (yield 60%) of the title compound.

[LCMS]: 651

[ Synthesis Example  4] Synthesis of Compound 7

6.0 g (12.6 mmol) of the compound of Preparation Example 1 (Core 1) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were added to 5.9 g (15.2 mmol) of dioxane. 100 mL of toluene was added. 0.16 g (0.7 mmol) of Pd (OAc) ₂ , 0.62 g (1.3 mmol) of XPhos, and 8.2 g (25.2 mmol) of Cs ₂ CO ₃ were added to the reaction solution, and the mixture was heated and refluxed at 120 for 4 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 3.9 g (yield 41%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 9.05 (s, 1H), 8.92 (m, 1H), 8.78 (d, 4H), 7.88 (m, 3H), 7.84 (s, 1H), 7.66 (d, 1H), 7.63 (d, 3H), 7.56 (m, 6H), 7.40 (d, 1H), 7.35 (t, 1H), 7.22 (m, 4H), 7.09 (t, 1H), 6.86 (m, 3H ), 6.42 (d, 2H), 2.05 (s, 3H), 1.96 (s, 3H)

[LCMS]: 754

[ Synthesis Example  5] Synthesis of Compound 11

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] of Preparation Example 1 and 2-([1,1'-diphenyl ] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine was subjected to the same procedure as in [Synthesis Example 7] to obtain 5.3 g of the target compound ( Yield 40%).

 [LCMS]: 831

[ Synthesis Example  6] Synthesis of Compound 13

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] and 2- (4-bromophenyl) -4 of Preparation Example 1 3.2 g (yield 58%) of the title compound was obtained in the same manner as in Synthesis Example 7, except that 6-diphenyl-1,3,5-triazine was used.

[LCMS]: 754

[ Synthesis Example  7] Synthesis of Compound 15

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] and 4- (4-bromophenyl) -2 of Preparation Example 1 3.6 g (yield 52%) of the title compound was obtained in the same manner as the Synthesis Example 7 except that 6-diphenylpyrimidine was used.

[LCMS]: 753

[ Synthesis Example  8] Synthesis of Compound 20

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] of Preparation Example 1 and 2- (3'-chloro- [1, 5.5 g of the target compound (yield) was carried out in the same manner as in Synthesis Example 2, except that 1'-diphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine was used. 42%).

[LCMS]: 831

[ Synthesis Example  9] Synthesis of Compound 26

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] of Preparation Example 1 and 4- (3'-chloro- [1, Except for using 1'-biphenyl] -3-yl) -2,6-diphenylpyrimidine, the same procedure as in Synthesis Example 2 was carried out to obtain 4.0 g (yield 45%) of the title compound.

[LCMS]: 830

[ Synthesis Example  10] Synthesis of Compound 31

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] of Preparation Example 1 and 2-([1,1'-biphenyl ] -4-yl) -4- (3'-chloro- [1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazine, except that Example 2] was carried out to obtain 2.5 g (yield 57%) of the title compound.

[LCMS]: 907

[ Synthesis Example  11] Synthesis of Compound 35

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,11'-indeno [1,2-b] carbazole] of Preparation Example 1 and 2- (3'-chloro- [1, 5.3 g (yield 46%) of the title compound was obtained in the same manner as in Synthesis Example 2, except that 1'-biphenyl] -3-yl) -4-phenylquinazolin was used.

[LCMS]: 804

[ Synthesis Example  12] Synthesis of Compound 37

10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole] of Preparation Example 2 and 2-chloro-4,6-diphenyl- Except for using 1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to obtain 6.2 g (yield 58%) of the title compound.

[LCMS]: 678

[ Synthesis Example  13] Synthesis of Compound 41

10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole] of Preparation Example 2 and 2-([1,1'-biphenyl ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was subjected to the same procedure as in Synthesis Example 1 to give 4.4 g of the target compound (yield 55%). Got it.

[LCMS]: 754

[ Synthesis Example  14] Synthesis of Compound 42

10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole] of Preparation Example 2 using 2-chloro-4-phenylquinazoline Except for the same procedure as in Synthesis Example 4, 3.5 g (yield 49%) of the title compound was obtained.

[LCMS]: 651

[ Synthesis Example  15] Synthesis of Compound 46

10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole] and 2- (3-chlorophenyl) -6 of Preparation Example 2; 2.7 g (yield 46%) of the title compound was obtained in the same manner as in Synthesis Example 4, except that 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine was used. .

[LCMS]: 792

[ Synthesis Example  16] Synthesis of Compound 53

10,10-dimethyl-10H, 11'H-spiro [anthracene-9,12'-indeno [2,1-a] carbazole] and 2- (3-chlorophenyl) -6 of Preparation Example 2; 3.5 g (yield 40%) of the title compound was obtained in the same manner as in Synthesis Example 4, except that 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine was used. .

[LCMS]: 831

[ Synthesis Example  17] Synthesis of Compound 55

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,7'-indeno [2,1-b] carbazole] and 2-chloro-4,6-diphenyl- in Preparation Example 3 5.4 g (yield 64%) of the title compound was obtained in the same manner as in Synthesis Example 1, except that 1,3,5-triazine was used.

[LCMS]: 678

[ Synthesis Example  18] Synthesis of Compound 60

Preparation Example 3 using 10,10-dimethyl-5'H, 10H-spiro [anthracene-9,7'-indeno [2,1-b] carbazole] and 2-chloro-4-phenylquinazoline Except that, the same procedure as in Synthesis Example 4 was carried out to obtain 4.9 g (yield 55%) of the title compound.

[LCMS]: 651

[ Synthesis Example  19] Synthesis of Compound 61

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,7'-indeno [2,1-b] carbazole] and 2- (3-bromophenyl) -4 of Preparation Example 3 5.0 g (yield 48%) of the title compound was obtained in the same manner as the Synthesis Example 4, except that, 6-diphenyl-1,3,5-triazine was used.

[LCMS]: 754

[ Synthesis Example  20] Synthesis of Compound 72

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,7'-indeno [2,1-b] carbazole] and 2- (4-chlorophenyl) -4- in Preparation Example 3 Except for using phenylquinazoline, the same procedure as in Synthesis Example 4 was carried out to obtain 3.9 g (yield 58%) of the title compound.

[LCMS]: 727

[ Synthesis Example  21] Synthesis of Compound 74

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,7'-indeno [2,1-b] carbazole] and 2- (4-chlorophenyl) -4- in Preparation Example 3 Except for using phenylquinazoline, the same procedure as in Synthesis Example 2 was carried out to obtain 2.5 g (yield 52%) of the title compound.

[LCMS]: 831

[ Synthesis Example  22] Synthesis of Compound 79

10,10-dimethyl-10H, 12'H-spiro [anthracene-9,7'-indeno [1,2-a] carbazole] and 2-chloro-4,6-diphenyl- of Preparation Example 4 Except for using 1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to obtain 3.3 g (yield 46%) of the title compound.

[LCMS]: 678

[ Synthesis Example  23] Synthesis of Compound 83

10,10-dimethyl-10H, 12'H-spiro [anthracene-9,7'-indeno [1,2-a] carbazole] and 2-([1,1'-biphenyl] in Preparation Example 4 ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was subjected to the same procedure as in [Synthesis Example 1] to give 6.3 g (yield 58%) of the title compound. Got it.

[LCMS]: 754

[ Synthesis Example  24] Synthesis of Compound 92

10,10-dimethyl-10H, 12'H-spiro [anthracene-9,7'-indeno [1,2-a] carbazole] of Preparation Example 4 and 2- (3'-chloro- [1, Except for using 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine. 54%).

[LCMS]: 831

[ Synthesis Example  25] Synthesis of Compound 98

10,10-dimethyl-10H, 12'H-spiro [anthracene-9,7'-indeno [1,2-a] carbazole] of Preparation Example 4 and 2- (3'-chloro- [1, 3.8 g (yield 44%) of the title compound was obtained in the same manner as [Synthesis Example 2], except that 1'-biphenyl] -3-yl) -4-phenylquinazolin was used.

[LCMS]: 804

[ Synthesis Example  26] Synthesis of Compound 100

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,8'-indeno [2,1-c] carbazole] and 2-chloro-4,6-diphenyl- of Preparation Example 5 Except for using 1,3,5-triazine, the same procedure as in Synthesis Example 1 was performed to obtain 5.5 g (yield 40%) of the title compound.

[LCMS]: 678

[ Synthesis Example  27] Synthesis of Compound 103

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,8'-indeno [2,1-c] carbazole] and 2-bromo-6,8-diphenyl of Preparation Example 5 6.1 g (yield 58%) of the title compound was obtained in the same manner as in Synthesis Example 1, except that [1,2,4] triazolo [1,5-a] pyridine was used.

[LCMS]: 716

[ Synthesis Example  28] Synthesis of Compound 112

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,8'-indeno [2,1-c] carbazole] and 2- (4-bromophenyl) -4 of Preparation Example 5 2.7 g (yield 62%) of the title compound was obtained in the same manner as in Synthesis Example 4, except that 6-diphenyl-1,3,5-triazine was used.

[LCMS]: 754

[ Synthesis Example  29] Synthesis of Compound 119

10,10-dimethyl-5'H, 10H-spiro [anthracene-9,8'-indeno [2,1-c] carbazole] of Preparation Example 5 and 2- (3'-chloro- [1, 3.4 g of the target compound was obtained in the same manner as in Synthesis Example 4, except that 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine was used. 53%).

[LCMS]: 831

[ Example  1 to 17] green organic Electric field  Fabrication of light emitting device

Compound 1, 4, 7, 11, 20, 26, 31, 37, 41, 46, 55, 61, 74, 79, 100, 103, 119 synthesized in the synthesis example was subjected to high purity sublimation purification Then, a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), washed with UV for 5 minutes and coated with a vacuum evaporator The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% of compound 1, 4, 7, 11, 20, 26, 31, 37, 41, 46, 55, on the prepared ITO transparent glass substrate (electrode) 63, 74, 79, 100, 103, 119 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) By laminating, a green organic electroluminescent device was manufactured.

[ Comparative example  1] Green Organic Electric field  Fabrication of light emitting device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a light-emitting host material.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used in Examples 1 to 17 and Comparative Example 1 are as follows.

[ Evaluation example  One]

For each of the green organic electroluminescent devices fabricated in Examples 1 to 17 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. .

Sample Host Driving voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 Compound 1 3.9 455 64.5 Example 2 Compound 4 3.8 457 62.5 Example 3 Compound 7 4.1 454 63.8 Example 4 Compound 11 4.2 454 58.2 Example 5 Compound 20 3.6 458 63.5 Example 6 Compound 26 3.5 457 60.9 Example 7 Compound 31 4.0 456 64.2 Example 8 Compound 37 3.9 455 63.0 Example 9 Compound 41 4.0 458 58.5 Example 10 Compound 46 3.8 457 63.1 Example 11 Compound 55 3.8 459 64.9 Example 12 Compound 61 3.6 459 62.4 Example 13 Compound 74 4.1 458 60.8 Example 14 Compound 79 4.5 454 59.5 Example 15 Compound 100 3.7 457 63.8 Example 16 Compound 103 4.1 457 65.5 Example 17 Compound 119 3.7 458 60.2 Comparative Example 1 CBP 5.4 459 44.2

As shown in Table 1, the case of applying the compound of the present invention (Examples 1 to 17) as a material of the light emitting layer included in the organic material layer of the green organic EL device (Examples 1 to 17) compared to the case of applying the conventional CBP (Comparative Example 1) It can be seen that the efficiency and driving voltage are excellent.

[ Example  18 to 31] Fabrication of Red Organic EL Device

Compounds 1, 6, 13, 15, 35, 42, 55, 60, 72, 79, 83, 98, 112, and 119 synthesized in the synthesis example were subjected to high purity sublimation purification in a conventionally known manner, and then A red organic electroluminescent device was produced.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% compound 1, 6, 13, 15, 35, 42, 55, 60, 72, 79, 83, 98, 112, 119 on the thus prepared ITO transparent electrode + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to fabricate an organic EL device. . The structures of m-MTDATA, TCTA, and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

[ Comparative example  2]

A red organic electroluminescent device was manufactured in the same manner as in Example 18, except that CBP was used instead of Compound 1 used as a light emitting host material in forming the emission layer in Example 18. The structure of CBP used was as described in Comparative Example 1.

[ Evaluation example  2]

For the organic electroluminescent devices manufactured in Examples 18 to 31 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 18 Compound 1 3.6 518 21.4 Example 19 Compound 6 3.5 519 20.8 Example 20 Compound 13 4.0 518 19.5 Example 21 Compound 15 3.4 520 22.4 Example 22 Compound 35 3.7 518 21.8 Example 23 Compound 42 3.8 520 20.4 Example 24 Compound 55 3.5 518 19.8 Example 25 Compound 60 3.4 519 21.0 Example 26 Compound 72 3.7 520 22.2 Example 27 Compound 79 3.9 519 19.7 Example 28 Compound 83 4.1 518 21.4 Example 29 Compound 98 3.6 518 22.6 Example 30 Compound 112 3.8 518 20.4 Example 31 Compound 119 3.8 518 21.2 Comparative Example 2 CBP 5.4 521 15.8

As shown in Table 2, in the case of the red organic EL device of Examples 18 to 31 using the compound according to the present invention as a light emitting layer material, efficiency and driving compared to the red organic electroluminescent device of Comparative Example 2 using the conventional CBP It was confirmed that the voltage was excellent.

[National R & D project supporting this invention]

[Project unique number] NRF-2016M3A7B4909246

[Department name] Ministry of Science and ICT

[Research Management Specialized Institution] Korea Research Foundation

[Name of research project] Nano material source technology development project

[Project name] Development of blue phosphorescent dopant for high efficiency long life AMOLED

[Contribution rate] 1/1

[Host] Kangwon National University

[Research Period] 2017.03.01 ~ 2018.02.28

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Claims (17)

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

[Formula 2]

In Chemical Formula 1 and Chemical Formula 2, At least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ is condensed with a ring represented by Formula 2 to form a condensed ring; The dotted line is the part where condensation takes place; l, m, n and p are each independently an integer from 0 to 4; R _1, R ₂ and Ar ₁ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, A C ₆ -C ₆₀ arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group; A ₁ to A ₄ and R ₃ to R ₆ which do not form a condensed ring with the ring represented by Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 To 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl group and C ₆ to C ₆₀ arylamine Selected from the group consisting of groups, and when there are a plurality of R ₃ to R ₆ , they are the same as or different from each other; An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyl jade of A ₁ to A ₄ , R ₁ to R ₆ and Ar ₁ which do not form a condensed ring with the ring represented by Formula 2 above The period, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group , Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 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, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ An aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, C ₆ ~ C ₆₀ Mono Or when substituted or unsubstituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 1, The compound is represented by any one of the following Chemical Formulas 3 to 8, the compound: [Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 3 to 8. R ₁ to R _6, A ₁ to A ₄ , l, m, n, p and Ar ₁ are as defined in claim ₁ . The method of claim 1, R ₁ and R ₂ are each independently selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, The alkyl group, aryl group and heteroaryl group of R ₁ and R ₂ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same or different from each other. The method according to claim 1, wherein Ar ₁ is a substituent represented by Formula 9: [Formula 9]

In Chemical Formula 9, * Means the part where the bond is made; L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms; R ₇ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group; Wherein L ₁ and the arylene group and a heteroarylene group, an alkyl group of the R ₇ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other. The method of claim 4, wherein Wherein L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of Formulas A-1 to A-4:

In Chemical Formulas A-1 to A-4, * Means the part where the coupling is made. The method of claim 4, wherein R ₇ is selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, The alkyl group, aryl group and heteroaryl group of R ₇ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When substituted or unsubstituted with a plurality of substituents, they are the same or different from each other. The method of claim 4, wherein R ₇ is a substituent represented by any one of Formulas 10 to 12: [Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 10 to 12, * Means the part where the bond is made; Z ₁ to Z ₅ are each independently N or C (R ₉ ); q is an integer from 0 to 4; R ₈ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Or a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring, and when R ₈ is a plurality, Same or different from each other; R ₉ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Or a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring, and when R ₉ is a plurality, Same or different from each other; Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R ₈ and R ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 7, wherein The substituent represented by the formula (10) is a substituent represented by the following formula (13): [Formula 13]

In Chemical Formula 13, * Means the part where the bond is made; R ₁₀ and R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, it said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of; Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₁₀ and R ₁₁ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other; Z ₁ , Z ₃ and Z ₅ are as defined in claim 7. The method of claim 7, wherein The substituent represented by Formula 10 is a substituent represented by any one of the following Formulas B-1 to B-3:

In Chemical Formulas B-1 to B-3, * Means the part where the coupling is made, R ₁₀ and R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the; Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₁₀ and R ₁₁ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 8, R ₁₀ and R ₁₁ are each independently selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms; The alkyl group, aryl group and heteroaryl group of R ₁₀ and R ₁₁ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 7, wherein The substituent represented by Formula 11 is a substituent represented by Formula 14 below: [Formula 14]

In Chemical Formula 14, * Means the part where the coupling is made, q, R ₈ and R ₉ are as defined in claim 7. The method of claim 11, R ₉ is selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms; The alkyl group, aryl group and heteroaryl group of R ₉ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When substituted or unsubstituted with a plurality of substituents, they are the same or different from each other. The method of claim 7, wherein The substituent represented by Formula 12 is a substituent represented by Formula 15: [Formula 15]

In Chemical Formula 15, * Means the part where the coupling is made, q and R ₈ are as defined in claim 7. The method of claim 13, R ₈ is selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms; The alkyl group, aryl group and heteroaryl group of R ₈ are each independently one or more substituents selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups When substituted or unsubstituted with a plurality of substituents, they are the same or different from each other. [Revision under Rule 91 02.01.2018]
The method of claim 1,
The compound is selected from the group consisting of the following compounds:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1. The method of claim 16, The organic material layer includes an organic electroluminescent device comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer and a light emitting layer.

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