WO2017105041A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. The compound according to the present invention is used for an organic material layer of an organic electroluminescent device, preferably a light emitting layer, an electron transport layer or an electron transport auxiliary layer, and thus can enhance the luminous efficiency, the driving voltage, the lifespan, etc. of the organic electroluminescent device.

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.

Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is 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.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. 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 a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

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

In order to solve the above problems, an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.

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

[Formula 1]

In Chemical Formula 1,

X is O or N (Ar ₂ );

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

o is an integer from 0 to 3;

Ar ₁ and Ar ₂ 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;

R ₁ to R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 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, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group, when each of the R ₁ to R ₄ plural are the same as each other or Different;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

The arylene group and the heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₄ , 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, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ of the Aryloxy group of -C ₆₀ , C ₁ -C ₄₀ alkyloxy group, arylamine group of C ₆ -C ₆₀ , cycloalkyl group of C ₃ -C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine blood When substituted or unsubstituted with one or more substituents selected from the group consisting of a silyl group and a C ₆ -C ₆₀ arylsilyl group, and substituted with a plurality of substituents, they may be the same or different from each other;

At least one of Ar ₂ and R ₁ to R ₄ is a substituent represented by Formula 2;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

L ₃ and L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

Ar ₃ 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;

The arylene group and heteroarylene group of L ₃ and L ₄ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of Ar ₃ Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C 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 substituted by one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be 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. .

"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 C2-C40 straight or branched chain unsaturated hydrocarbon 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 at least one carbon-carbon triple bond, 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 to 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 of 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.

The compound represented by Formula 1 according to the present invention has excellent thermal stability, hole transporting, hole injection performance, electron transporting and electron injection performance, and has excellent phosphorescence characteristics as a light emitting layer, and thus can be used as an organic material layer material of an organic EL device. Can be.

In addition, when the novel compound represented by Chemical Formula 1 of the present invention is used as a material of an electron transporting layer or an electron transporting auxiliary layer, an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life, as compared with the conventional materials Can be manufactured, and further, a full color display panel with greatly improved performance and lifetime can be manufactured.

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.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

X is O or N (Ar ₂ );

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

o is an integer from 0 to 3;

Ar ₁ and Ar ₂ 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;

R ₁ to R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 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, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group, when each of the R ₁ to R ₄ plural are the same as each other or Different;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

The arylene group and the heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₄ , 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, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ of the Aryloxy group of -C ₆₀ , C ₁ -C ₄₀ alkyloxy group, arylamine group of C ₆ -C ₆₀ , cycloalkyl group of C ₃ -C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine blood When substituted or unsubstituted with one or more substituents selected from the group consisting of a silyl group and a C ₆ -C ₆₀ arylsilyl group, and substituted with a plurality of substituents, they may be the same or different from each other;

At least one of Ar ₂ and R ₁ to R ₄ is a substituent represented by Formula 2;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

L ₃ and L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

Ar ₃ 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;

The arylene group and heteroarylene group of L ₃ and L ₄ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of Ar ₃ Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C 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 substituted by one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The novel organic compounds according to the present invention include nitrogen-containing heterocycles (e.g., pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) in moieties of spirofluorene xanthene or spiroacridinfluorene, and the like. Likewise, electron withdrawals (EWGs) with high electron absorption form a basic skeleton connected by various linkers (phenyl, biphenyl, naphthalene, fluorene, carbazolyl, phenanthrene, etc.). Specifically, it is characterized in that the compound represented by the formula (1):

[Formula 1]

In Chemical Formula 1,

X is O or N (Ar ₂ );

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

o is an integer from 0 to 3;

Ar ₁ and Ar ₂ 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;

R ₁ to R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 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, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group, when each of the R ₁ to R ₄ plural are the same as each other or Different;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

The arylene group and the heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₄ , 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, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ of the Aryloxy group of -C ₆₀ , C ₁ -C ₄₀ alkyloxy group, arylamine group of C ₆ -C ₆₀ , cycloalkyl group of C ₃ -C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine blood When substituted or unsubstituted with one or more substituents selected from the group consisting of a silyl group and a C ₆ -C ₆₀ arylsilyl group, and substituted with a plurality of substituents, they may be the same or different from each other;

At least one of said Ar ₂ and R ₁ to R ₄ is a substituent represented by the formula (2), all of which are the same or different from each other to at least two of the Ar ₂ and R ₁ to R ₄ when the substituent represented by the formula (2) To;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

L ₃ and L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

Ar ₃ 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;

The arylene group and heteroarylene group of L ₃ and L ₄ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of Ar ₃ Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C 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 substituted with one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be the same or different from each other.

In the compound represented by Formula 1 in the present invention, the moiety of spirofluorene xanthene or spiroacridine fluorene is basically excellent electrochemical stability, high glass transition temperature and carrier transport ability In particular, the electron mobility is very excellent, and the blue light emission efficiency is increased. 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.

For this reason, the compound represented by the formula (1) of the present invention has excellent electron transport ability and light emission characteristics, and thus, any one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer, which are the organic material layers of the organic EL device. Can be used as a material. Preferably a light emitting layer; Electron transport layer; And an electron transport auxiliary layer further stacked on the electron transport layer. It may be used as a material of any one, and more preferably may be used as a material of the electron transport layer or the electron transport auxiliary layer.

In addition, since the compound represented by Formula 1 of the present invention has a high triplet energy, it can exhibit an excellent efficiency increase due to the triplet-triplet fusion effect, and most preferably as a material for the electron transport auxiliary layer. Can be used. In detail, the compound represented by Chemical Formula 1 may prevent the exciton generated in the emission layer from diffusing into the electron transport layer or the hole transport layer adjacent to the emission layer. As a result, the number of excitons that contribute to light emission in the light emitting layer may be increased, and thus the light emitting efficiency of the device may be improved, and the durability and stability of the device may also be improved, thereby effectively increasing the life of the device. 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 represented by Formula 1 may be represented by the following formula (3):

[Formula 3]

In Chemical Formula 3,

L ₁ , L ₂ , R ₁ to R ₃ , Ar ₁ , l, m and n are each as defined in Chemical Formula 1.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be represented by the following formula (4) or 5, preferably a compound represented by the following formula (4):

[Formula 4]

[Formula 5]

In Chemical Formulas 4 and 5,

L ₁ , L ₂ , R ₁ to R ₃ , Ar ₁ , l, m and n are each as defined in Chemical Formula 1.

The compound represented by Formula 4 of the present invention has a substituent at position 2 corresponding to the active site of the fluorene type core in the moiety of spirofluorene xanthene or spiroacridine fluorene By being connected, the physicochemical properties of the material to which the compound is applied can be stabilized, and high current efficiency and low driving voltage can be ensured.

According to one preferred embodiment of the present invention, Ar ₁ is preferably a substituent represented by the following formula (6) in terms of luminous efficiency, but is not limited thereto:

[Formula 6]

In Chemical Formula 6,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₅ ), but at least one of Z ₁ to Z ₅ is N;

R ₅ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ arylamine 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 phospha Condensed in combination with an adjacent group (e.g., L ₂ , adjacent other R ₅ ), or selected from the group consisting of a silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group and a C ₆ -C ₆₀ arylsilyl group Ring may be formed, and when there are a plurality of R ₅ , they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R ₅ , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, specific examples of the substituent represented by Formula 6 include a substituent represented by Formulas A-1 to A-15, but are not limited thereto.

In Chemical Formulas A-1 to A-15,

p is an integer from 0 to 4;

q is an integer from 0 to 3;

r is an integer from 0 to 2

R ₆ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl 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 ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group consisting of, or combine with adjacent groups (e.g. R ₅ or other R ₆ etc.) to form a condensed ring When R ₆ is plural, they are the same as or different from each other;

Alkyl group of the R _6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, these are the same or may be different from one another, and;

* And R ₅ are each as defined in Chemical Formula 6.

According to one preferred embodiment of the present invention, Ar ₁ is preferably a substituent represented by the following formula (7) in terms of luminous efficiency, but is not limited thereto:

[Formula 7]

In Chemical Formula 7,

* Means the part where the bond is made;

Y ₁ to Y ₃ are each independently N or C (R ₇ ), but at least one of Y ₁ to Y ₃ is N;

Y ₄ is N (R ₈ ) or C (R ₉ ) (R ₁₀ );

R ₇ to R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, the adjacent groups (e.g., L _2, the other R adjacent ₇ , R ₈ , R ₉ or R ₁₀ ) may be combined to form a condensed ring, and when there are a plurality of R ₇ , they are the same as or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₇ to R ₁₀ 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 of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, specific examples of the substituent represented by Formula 7 include the substituents represented by the following Formulas B-1 to B-11, but are not limited thereto.

In Chemical Formulas B-1 to B-11,

s is an integer from 0 to 2;

t is an integer from 0 to 4;

R ₁₁ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, A C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylsilyl group, or an adjacent group (eg, any one of R ₇ to R ₁₀ or another R _11, etc.) May be joined to form a condensed ring, and when there are a plurality of R ₁₁ , they are the same or different from each other;

Alkyl group of the R _11, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ At least one member selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diaryl phosphinyl group, and a C ₆ to C ₆₀ arylsilyl group When unsubstituted or substituted with a substituent, and substituted with a plurality of substituents, they may be the same as or different from each other;

*, R ₇ to R ₁₀ are each as defined in Chemical Formula 7.

According to one preferred embodiment of the present invention, the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 8 to 12:

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 8 to 12,

p and t are each independently an integer from 0 to 4;

q is an integer from 0 to 3;

r is an integer from 0 to 2;

R ₅ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ arylamine 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 phospha Nyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylsilyl group selected from the group consisting of, or adjacent groups (e.g., L ₂ , other adjacent R ₅ or R ₆ ) and Can combine to form a condensed ring;

R ₆ and R ₁₁ 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 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to C ₆₀ An arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group, or an adjacent group (e.g., L ₂ , other adjacent R ₅ , R ₆ or R _11, etc.) to form a condensed ring, and each of R ₆ and R ₁₁ is the same as 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 of R ₅ , R ₆ and R ₁₁ 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 alkyl group, C ₂ ~ C ₄₀ alkenes group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C _60, alkyloxy group of C ₁ ~ C ₄₀ of the , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group , C group ₆ to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphazene group, C ₆ to C ₆₀ mono or diaryl phosphine blood group and a C ₆ to line from the group consisting of C ₆₀ aryl silyl A substituted or unsubstituted by one or more substituent species, when it is substituted with a plurality of substituents, these are the same or may be different from one another, and;

X, l, m, n, R ₁ , R ₂ , R ₃ , L ₁ and L ₂ are each as defined in Formula 1.

According to one preferred embodiment of the present invention, L ₁ to L ₄ may be each independently selected from the group consisting of a single bond, phenylene group, biphenylene group, naphthalenyl group, fluorenyl group and carbazolyl group, preferably Preferably it may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group, and more preferably may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group. Both L ₁ and L ₂ may not be a single bond.

In the present invention, when at least one of L ₁ and L ₂ is a phenylene group, a biphenylene group or a naphthalenyl group, HOMO and LUMO, which are basic physical properties of the material, are changed, and more specifically, both L ₁ and L ₂ Compared to the single bond case, the LUMO level of the material rises, resulting in a wider band gap, resulting in higher current efficiency and lower drive voltage. Most preferably, at least one of L ₁ and L ₂ may be a phenylene group or a biphenylene group.

According to a preferred embodiment of the present invention, L ₁ and L ₂ may be each independently a single bond or a linker represented by any one of the following formulas C-1 to C-12, preferably L ₁ and L ₂ may be each independently a linker represented by one of Formulas C-1 to C-12:

In Chemical Formulas C-1 to C-12,

* Means the part where the coupling is made.

According to one preferred embodiment of the present invention, L ₁ and L ₂ are each independently a single bond, or the formula C-2, C-3, C-7, C-8, C-9, C-10 and It may be a linker represented by any one of C-11, wherein both L ₁ and L ₂ may not be a single bond, more preferably the L ₁ and L ₂ are each independently of the formulas C-2, C-3, It may be any one of linkers represented by C-7, C-8, C-9, C-10 and C-11.

In the present invention, the linkers represented by the formulas C-2, C-3, C-7, C-8, C-9, C-10, and C-11 have a steric hindrance effect, and thus include the above linker. When the compound is used as a material for an electron transport auxiliary layer, an additional efficiency synergistic effect is expected by preventing excitons from flowing over the emission layer due to the TTF (triplet-triplet fusion) effect caused by the increase of the T1 (triplet energy) value of the material. Most preferably, L ₁ and L ₂ may be independently a linker represented by any one of Formulas C-2, C-7, C-8, and C-9.

According to a preferred embodiment of the present invention, at least one of the R ₁ to R ₃ may be selected from the group consisting of halogen, cyano group and C ₆ ~ C ₆₀ aryl group, preferably halogen, cyano group, phenyl group And it may be selected from the group consisting of a biphenyl group, more preferably the R ₃ may be a halogen or a cyano group.

According to a preferred embodiment of the present invention, R ₅ to R ₁₁ are each independently hydrogen, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and nuclear atoms 5 to 60 It may be selected from the group consisting of three heteroaryl groups, wherein the alkyl group, aryl group and heteroaryl group of R ₅ to R ₁₁ are each independently one or more selected from the group consisting of halogen, cyano group and C ₆ ~ C ₆₀ aryl group When substituted or unsubstituted with a substituent and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₅ to R ₁₁ are each independently hydrogen, halogen, cyano group, phenyl group, biphenyl group, naphthalenyl group, carbazolyl group, fluorenyl group and pyridinyl group It may be selected, the phenyl group, biphenyl group, naphthalenyl group, carbazolyl group, fluorenyl group and pyridinyl group of the R ₅ to R ₁₁ are each independently selected from the group consisting of halogen, cyano group, phenyl group and biphenyl group When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they may be the same or different from each other.

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

In the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. Organic 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 stacked on top of the electron transport layer to facilitate the injection of electrons from the cathode to perform a function that ultimately improves the power efficiency, which is specially used in the art It can be used without limitation, and 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 life improvement layer, and thus cannot diffuse or move to the electron transport layer, and consequently, the hole is 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 moiety of spirofluorene xanthene or spiroacridine fluorene of the compound represented by Formula 1 is basically excellent in electrochemical stability, high glass transition temperature and carrier transport ability, The mobility is also very good, showing the characteristics that the blue luminous efficiency is increased. In addition, the materials represented by Chemical Formula 1 are structural features of combining the core core and the electron-withdrawing group (EWG), the electron mobility is particularly excellent, the glass transition temperature and the thermal stability is excellent. Therefore, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, an electron transporting layer, or an electron transporting auxiliary layer, and more preferably, an electron transporting layer or an electron transporting auxiliary layer.

In addition, in the present invention, since the compound represented by Chemical Formula 1 has a high triplet energy, it may exhibit an excellent efficiency increase due to a triplet-triplet fusion (TTF) effect, and more preferably as a material for the electron transport auxiliary layer. Can be used. In more detail, in the present invention, the compound represented by Chemical Formula 1 may prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. As a result, the number of excitons that contribute to light emission in the light emitting layer may be increased, and thus the light emitting efficiency of the device may be improved, and the durability and stability of the device may also be improved, thereby effectively increasing the life of the device. 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 invention, the present invention is not limited by the following examples.

Example

[ Preparation  1] Synthesis of Core 1

2- Of bromospyro [fluorene-9,9'-xanthene]  synthesis

50 g (0.19 mol) of 2-bromo-9H-fluorene-9-one and 181.6 g (1.93 mol) of phenol were added 501. mL (0.77 mol) of methanesulfonic acid. The mixed solution was heated to reflux at 120 ° C for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 1.0 L of CH ₂ Cl ₂ , and the separated organic layer was neutralized with 500 mL of saturated calcium carbonate and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 59.5 g (yield 75%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 7.78 (d, 1H), 7.65 (d, 1H), 7.50 (d, 1H), 7.38 (t, 1H), 7.27 (d, 1H), 7.25 (m, 5H), 7.15 (d, 1H), 6.79 (t, 2H), 6.41 (d, 2H)

[LCMS]: 411

[ Preparation  2] Synthesis of Core 2

<Step 1> 3- Bromo -9H- Fluorene Synthesis of -9-one

To 30 g (0.10 mol) of 3-bromophenanthrene-9,10-dione and 46.9 g (0.84 mol) of KOH was added 500 mL of purified water. The mixture was heated to reflux for 12 hours. Then 49.5 g (0.31 mol) of KMnO ₄ were slowly added to the reaction solution three times. After heating under reflux for 12 hours, the reaction solution was cooled to room temperature. The resulting solid was filtered, washed with purified water and dried with hot air to obtain 12.2 g (yield 45%) of the title compound.

¹ H-NMR (in DMSO): δ 8.13 (d, 1H), 7.88 (d, 1H), 7.65 (m, 2H), 7.58 (dd, 2H), 7.53 (d, 1H), 7.42 (t, 1H )

[LCMS]: 259

<Step 2> 3- Of bromospyro [fluorene-9,9'-xanthene]  synthesis

15.6 g (yield 82%) of the title compound corresponding to the structural isomers of Core 1 were obtained by the same procedure as in [Preparation Example 1].

[LCMS]: 411

[ Preparation 3] Core  3, composite

<Step 1> 2- Bromo -9- (2- ( Diphenylamino ) Phenyl) -9H- Fluorene Synthesis of -9-ol

To 45 g (0.14 mol) of 2-bromo-N, N-diphenylaniline was added 500 mL of THF. Then, the temperature of the reaction solution was lowered to -78 ° C, 36.0 g (0.14 mol) of 2-bromo-9-fluorenone was dissolved in 500 mL of THF, slowly added to the reaction solution, and stirred at the same temperature for 1 hour. It was further stirred at room temperature for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, extracted with EA 1.5 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 46.2 g (yield 66%) of the title compound.

[LCMS]: 504

<Step 2> 2'- Bromo -10-phenyl-10H-spiro [acridin-9,9'- Fluorene Synthesis

460 mL of AcOH was added to 46.0 g (0.09 mol) of 2-bromo-9- (2- (diphenylamino) phenyl) -9H-fluorene-9-ol. The reaction solution was heated to reflux at 100 ° C. for 2 hours. After cooling the temperature to room temperature, 500 mL of purified water was added to the reaction solution to terminate the reaction, and the resulting solid was filtered under reduced pressure and dried with hot air to obtain 38.1 g (yield 86%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 7.75 (d, 1H), 7.69 (t, 2H), 7.60 (d, 1H), 7.57 (m, 2H), 7.49 (m, 3H), 7.39 (m, 2H), 7.29 (dd, 1H), 6.94 (t, 2H), 6.58 (t, 2H), 6.36 (m, 4H)

[LCMS]: 486

[ Preparation  4] Synthesis of Core 4

<Step 1> 3- Bromo -9- (2- ( Diphenylamino ) Phenyl) -9H- Fluorene Synthesis of -9-ol

20.5 g (79%) of the title compound corresponding to the structural isomers of Core 3 were obtained by the same process as Step 1 of [Preparation Example 3].

[LCMS]: 504

<Step 2> 3'- Bromo -10-phenyl-10H-spiro [acridin-9,9'- Fluorene Synthesis

18.5 g (88%) of the target compound corresponding to the structural isomers of Core 3 were obtained by the same process as Step 2 of [Preparation Example 3].

¹ H-NMR (in CDCl ₃ ): δ 7.92 (d, 1H), 7.70 (m, 3H), 7.56 (m, 1H), 7.47 (m, 2H), 7.35 (m, 3H), 7.27 (m, 2H), 6.90 (m, 2H), 6.55 (m, 2H), 6.34 (m, 4H)

[LCMS]: 486

[ Preparation  5] 4,4,5,5- Tetramethyl -2- (Spyro [ Fluorene Synthesis of -9,9'-Xanthene] -2-yl) -1,3,2-dioxaborolane

25.0 g (60.8 mmol) of 2-bromospyro [fluorene-9,9'-xanthene] synthesized in Preparation Example 1 and 4,4,4 ', 4', 5,5,5 ' 500 mL of dioxane was added to 18.5 g (72.9 mmol) of 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane). Next, 2.5 g (3.0 mmol) of Pd (dppf) Cl ₂ and 17.9 g (182 mmol) of KOAc were added thereto, followed by heating to reflux for 4 hours at 130 ° C. Then, the reaction mixture was cooled to room temperature and 500 mL of an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 20.3 g (yield 73%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 7.87 (d, 1H), 7.79 (dd, 2H), 7.57 (s, 1H), 7.34 (dt, 1H), 7.21 (m, 3H), 7.18 (m, 2H), 7.11 (dd, 1H), 6.74 (dt, 2H), 6.35 (dd, 2H), 1.28 (s, 12H)

[LCMS]: 458

[ Preparation  6] 4,4,5,5- Tetramethyl -2- (Spyro [ Fluorene Synthesis of -9,9'-Xanthene] -3-yl) -1,3,2-dioxaborolane

Same as [Preparation 5], except that 3-bromospyro [fluorene-9,9'-xanthene] was used instead of 2-bromospyro [fluorene-9,9'-xanthene]. The procedure was carried out to obtain 12.6 g (yield 79%) of the title compound.

[LCMS]: 458

[ Preparation  7] 10-phenyl-2 '-(4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran Synthesis of 2-yl) -10H-spiro [acridin-9,9'-fluorene]

Except for using 2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] instead of 2-bromospyro [fluorene-9,9'-xanthene] 15.5 g (yield 82%) of the title compound were obtained in the same manner as in [Preparation Example 5].

[LCMS]: 533

[ Preparation  8] 10-phenyl-2 '-(4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran Synthesis of 2-yl) -10H-spiro [acridin-9,9'-fluorene]

Except for using 3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] instead of 2-bromospyro [fluorene-9,9'-xanthene] Then, the same procedure as in [Preparation Example 5], to obtain 13.8 g (yield 80%) of the target compound.

[LCMS]: 533

[ Preparation  9] 2- Bromo -7- Of phenylspiro [fluorene-9,9'-xanthene]  synthesis

<Step 1> 2,7- Of dibromospyro [fluorene-9,9'-xanthene]  synthesis

A target compound 28.0 was prepared by the same procedure as in [Preparation Example 1], except that 2,7-dibromo-9H-fluorene-9-one was used instead of 2-bromo-9H-fluorene-9-one. g (yield 77%) was obtained.

[LCMS]: 490

<Step 2> 2- Bromo -7- Of phenylspiro [fluorene-9,9'-xanthene]  synthesis

To 28 g (57.1 mmol) of 2,7-dibromospyro [fluorene-9,9'-xanthene] synthesized above and 7.0 g (57.1 mmol) of phenylboronic acid, 600 mL of dioxane, H ₂ O 150 mL was added. 3.3 g (2.9 mmol) of Pd (PPh ₃ ) _{4 and} 23.7 g (171 mmol) of K ₂ CO ₃ were added and heated to reflux at 120 ° C. for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 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 23.1 g (yield 83%) of the title compound.

[LCMS]: 487

[ Synthesis Example  1] Synthesis of Compound 1

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5; Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine, the same procedure as in <Step 2> of [Preparation 9] was carried out to obtain 5.7 g of the target compound (64% yield). Got.

[LCMS]: 563

[ Synthesis Example  2] Synthesis of Compound 4

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5; <Step 2 of Preparation Example 9>, except that 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was used 4.5 g (yield 52%) of the title compound was obtained by performing the same procedure as described above.

¹ H-NMR (in CDCl ₃ ): δ 8.93 (d, 1H), 8.75 (d, 2H), 8.70 (d, 2H), 8.55 (s, 1H), 7.90 (d, 1H), 7.76 (d, 2H), 7.68 (d, 2H), 7.56 (m, 3H), 7.50 (t, 2H), 7.38 (t, 2H), 7.24 (m, 3H), 7.17 (d, 1H), 6.80 (t, 2H ), 6.50 (d, 2 H)

[LCMS]: 639

[ Synthesis Example  3] Synthesis of Compound 5

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5; Except for using 4-([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine, the same procedure as in <Step 2> of [Preparation 9] was performed. 6.6 g (62% yield) of compound were obtained.

¹ H-NMR (in CDCl ₃ ): δ 8.67 (dd, 2H), 8.52 (dd, 1H), 8.30 (dd, 2H), 8.01 (d, 1H), 7.98 (d, 1H), 7.89 (s, 1H), 7.87 (d, 1H), 7.74 (dd, 2H), 7.66 (dd, 2H), 7.52 (m, 3H), 7.46 (d, 2H), 7.41 (t, 2H), 7.30 (d, 2H ), 7.24 (m, 4H), 6.81 (t, 2H), 6.49 (d, 2H)

[LCMS]: 638

[ Synthesis Example  4] Synthesis of Compound 8

2-bromospyro [fluorene-9,9'-xanthene] of Preparation Example 1 and 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3 3.5 g of the target compound was carried out in the same manner as in <Step 2> of [Preparation Example 9], except that 2-, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. (Yield 55%) was obtained.

¹ H-NMR (in CDCl ₃ ): δ 8.89 (s, 1H), 8.72 (m, 4H), 8.67 (dd, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (dd, 1H), 7.73 (dd, 1H), 7.59 (m, 8H), 7.40 (t, 1H), 7.24 (m, 6H), 6.82 (t, 2H), 6.50 (dd, 2H)

[LCMS]: 639

[ Synthesis Example  5] Synthesis of Compound 14

2-bromospyro [fluorene-9,9'-xanthene] and 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3- in Preparation Example 1 [Preparation 9], except that (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. 4.8 g (yield 60%) of the title compound was obtained in the same manner as in <Step 2>.

¹ H-NMR (in CDCl ₃ ): δ 8.91 (s, 1H), 8.80 (d, 2H), 8.74 (dd, 2H), 8.70 (d, 1H), 7.94 (d, 1H), 7.85 (d, 1H), 7.77 (m, 3H), 7.72 (m, 3H), 7.57 (m, 7H), 7.42 (m, 2H), 7.24 (m, 4H), 7.15 (dd, 2H), 6.80 (t, 2H ), 6.51 (dd, 2H)

[LCMS]: 715

[ Synthesis Example  6] Synthesis of Compound 15

2-bromospyro [fluorene-9,9'-xanthene] and 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3- of Preparation Example 1 Same as <Step 2> of [Preparation Example 9], except that (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used. The procedure was carried out to obtain 5.5 g (yield 45%) of the title compound.

¹ H-NMR (in CDCl ₃ ): δ 8.70 (m, 2H), 8.43 (s, 1H), 8.35 (d, 2H), 8.16 (d, 1H), 8.03 (s, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.77 (d, 2H), 7.75 (d, 1H), 7.68 (d, 2H), 7.63 (d, 1H), 7.50 (m, 7H), 7.40 (t, 2H ), 7.24 (m, 5H), 6.80 (t, 2H), 6.50 (d, 2H)

[LCMS]: 714

[ Synthesis Example  7] Synthesis of Compound 18

2-bromospyro [fluorene-9,9'-xanthene and 4-phenyl-2- (3- (4,4,5,5-tetramethyl-1,3,2-di in Preparation Example 1) Except for using oxaborolan-2-yl) phenyl) quinazoline, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain a target compound 7.2 g (yield 65%).

[LCMS]: 612

[ Synthesis Example  8] Synthesis of Compound 20

2-bromospyro [fluorene-9,9'-xanthene] and 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-A in Preparation Example 1 5.8 g (yield 46%) of the title compound was obtained in the same manner as in <Step 2> of [Preparation Example 9], except that [] pyridine was used.

[LCMS]: 677

[ Synthesis Example  9] Synthesis of Compound 22

2-bromospyro [fluorene-9,9'-xanthene] of Preparation Example 1 and 2,4-diphenyl-6- (3 '-(4,4,5,5-tetramethyl-1, Preparation Example 9, except that 3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5-triazine was used 3.2 g (yield 55%) of the title compound were obtained in the same manner as in <Step 2>.

¹ H-NMR (in DMSO): δ 8.89 (s, 1H), 8.71 (m, 5H), 8.15 (d, 1H), 8.02 (dd, 2H), 7.90 (d, 1H), 7.85 (s, 1H ), 7.71 (m, 4H), 7.65 (m, 4H), 7.54 (d, 2H), 7.47 (s, 1H), 7.42 (t, 1H), 7.26 (m, 5H), 7.08 (d, 1H) , 6.74 (t, 2H), 6.36 (d, 2H)

[LCMS]: 715

[ Synthesis Example  10] Synthesis of Compound 31

2-bromospyro [fluorene-9,9'-xanthene] and 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3 'of Preparation Example 1 -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5 Except for using triazine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 5.5 g (yield 40%) of the title compound.

[LCMS]: 791

[ Synthesis Example  11] Synthesis of Compound 37

2-bromospyro [fluorene-9,9'-xanthene] and 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3 'of Preparation Example 1 With the exception of using-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) pyrimidine Then, the same procedure as in <Step 2> of [Preparation Example 9] was performed to obtain 6.0 g (yield 44%) of the title compound.

[LCMS]: 790

[ Synthesis Example  12] Synthesis of Compound 44

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5 6.0 g (13.1 mmol) and 2- (3 ''-chloro- [1,1 ': 3', 1 ''-terphenyl] -3-yl) -4,6-diphenyl-1,3,5- To 6.5 g (13.1 mmol) of triazine was added 200 mL of dioxane and 50 mL of H ₂ O. 0.15 g (0.7 mmol) of Pd (OAc) ₂ , 0.62 g (1.3 mmol) of XPhos, and 8.5 g (26.2 mmol) of Cs ₂ CO ₃ were added thereto, and the mixture was heated and refluxed at 120 ° C. for 5 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of purified water. The mixture was extracted with 1 L 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 5.2 g (yield 54%) of the title compound.

[LCMS]: 791

[ Synthesis Example  13] Synthesis of Compound 52

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -3-yl) -1,3,2-dioxaborolane of Preparation Example 6 2 [Step 2] of [Preparation Example 9], except that-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was used The same procedure was followed to obtain 4.5 g (yield 50%) of the title compound.

[LCMS]: 639

[ Synthesis Example  14] Synthesis of Compound 53

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -3-yl) -1,3,2-dioxaborolane of Preparation Example 6; Except for using 4-([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine, the same procedure as in <Step 2> of [Preparation 9] was performed. 4.0 g (46% yield) of compound was obtained.

[LCMS]: 638

[ Synthesis Example  15] Synthesis of Compound 56

3-bromospyro [fluorene-9,9'-xanthene] of Preparation Example 2 and 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3 7.2 g of the target compound was carried out in the same manner as in <Step 2> of [Preparation Example 9], except that 2,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. (Yield 65%) was obtained.

[LCMS]: 639

[ Synthesis Example  16] Synthesis of Compound 59

3-bromospyro [fluorene-9,9'-xanthene] of Preparation Example 2 and 4,6-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3 3.6 g (yield 45%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that, 2-dioxaborolan-2-yl) phenyl) pyrimidine was used. .

[LCMS]: 638

[ Synthesis Example  17] Synthesis of Compound 70

Preparation Example 2 3-bromospyro [fluorene-9,9'-xanthene] and 2,4-diphenyl-6- (3 '-(4,4,5,5-tetramethyl-1,3,2 <Step 2 of Preparation 9>, except that -dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5-triazine was used 6.3 g (yield 58%) of the title compound were obtained by the same procedure as the>.

[LCMS]: 715

[ Synthesis Example  18] Synthesis of Compound 79

3-bromospyro [fluorene-9,9'-xanthene] and 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3 'of Preparation Example 2 -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5 5.7 g (yield 62%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that triazine was used.

[LCMS]: 791

[ Synthesis Example  19] Synthesis of Compound 82

3-bromospyro [fluorene-9,9'-xanthene] and 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3 'of Preparation Example 2 Except for using-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) pyrimidine Then, the same procedure as in <Step 2> of [Preparation Example 9] was carried out to obtain 4.0 g (yield 45%) of the target compound.

[LCMS]: 790

[ Synthesis Example  20] Synthesis of Compound 91

3-bromospyro [fluorene-9,9'-xanthene] of Preparation Example 2 and 6,8-diphenyl-2- (4 '-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl)-[1,2,4] triazolo [1,5-a] pyridine Except for the same procedure as in <Step 2> of [Preparation Example 9], 4.3 g (yield 52%) of the title compound was obtained.

[LCMS]: 753

[ Synthesis Example  21] Synthesis of Compound 97

10-phenyl-2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9 of Preparation Example 7 , 9'-fluorene] and 2-chloro-4,6-diphenyl-1,3,5-triazine except for using the same procedure as in <Step 2> of [Preparation Example 9] 6.5 g (68% yield) of compound was obtained.

[LCMS]: 638

[ Synthesis Example  22] Synthesis of Compound 102

10-phenyl-2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9 of Preparation Example 7 , 9'-fluorene] and 2-chloro-4-phenylquinazoline were used in the same manner as in <Step 2> of [Preparation Example 9], to obtain 4.3 g (yield 50%) of the title compound. .

[LCMS]: 611

[ Synthesis Example  23] Synthesis of Compound 114

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] of Preparation Example 3 and 4-phenyl-2- (3- (4,4,5,5- Except for using tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) quinazolin, the same procedure as in <Step 2> of [Preparation 9] was carried out to obtain 4.3 g ( Yield 50%).

[LCMS]: 687

[ Synthesis Example  24] Synthesis of Compound 118

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation 9], 2.5 g (yield 38%) of the title compound was obtained.

¹ H-NMR (in DMSO): δ 8.90 (s, 1H), 8.73 (m, 5H), 8.11 (d, 1H), 8.06 (m, 2H), 7.92 (dd, 2H), 7.71 (m, 7H ), 7.68 (m, 7H), 7.51 (dd, 2H), 7.40 (m, 2H), 7.31 (t, 1H), 6.96 (t, 2H), 6.58 (t, 2H), 6.32 (dd, 2H) , 6.22 (dd, 2H)

[LCMS]: 790

[ Synthesis Example  25] Synthesis of Compound 128

10-phenyl-2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9 of Preparation Example 7 , 9'-fluorene] and 2- (3 ''-chloro- [1,1 ': 3', 1 ''-terphenyl] -3-yl) -4,6-diphenyl-1,3, Except for using 5-triazine, the same procedure as in <Step 2> of [Preparation Example 9] was performed to obtain 4.4 g (yield 52%) of the title compound.

[LCMS]: 867

[ Synthesis Example  26] Synthesis of Compound 134

10-phenyl-3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9, of Preparation Example 8; <Step 2 of Preparation Example 9>, except that 9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine were used. 5.6 g (yield 60%) of the title compound was obtained by the same procedure as the above.

[LCMS]: 713

[ Synthesis Example  27] Synthesis of Compound 136

10-phenyl-3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9 of Preparation Example 8 [9] -fluorene] and 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine except that < 5.0 g (yield 55%) of the title compound was obtained by the same procedure as in Step 2>.

[LCMS]: 676

[ Synthesis Example  28] Synthesis of Compound 141

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 4 [Example of preparation except that 2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used 9] was obtained in the same manner as in <Step 2>, to obtain 5.3 g (yield 52%) of the title compound.

[LCMS]: 789

[ Synthesis Example  29] Synthesis of Compound 145

2-Bromo-7-phenylspiro [fluorene-9,9'-xanthene] and 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6 of Preparation Example 9 Except that 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine is used [ 4.6 g (yield 55%) of the title compound was obtained in the same manner as <Step 2> of Preparation Example 9].

[LCMS]: 791

[ Synthesis Example  30] Synthesis of Compound 147

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5; Except for using 2- (6-chloronaphthalen-2-yl) -4,6-diphenyl-1,3,5-triazine, the same procedure as in <Step 2> of [Preparation Example 9] was performed. 5.5 g (yield 43%) of the title compound were obtained.

[LCMS]: 689

[ Synthesis Example  31] Synthesis of Compound 149

4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane of Preparation Example 5; Except that 2-([1,1'-biphenyl] -4-yl) -4- (6-chloronaphthalen-2-yl) -6-phenyl-1,3,5-triazine was used [ 3.0 g (yield 42%) of the title compound was obtained in the same manner as in <Step 2> of Preparation Example 9].

[LCMS]: 765

[ Synthesis Example  32] Synthesis of Compound 104

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3- (4,4,5) of Preparation Example 3 [Step 2] of [Preparation Example 9], except that, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. The same procedure was followed to obtain 4.5 g (yield 62%) of the title compound.

[LCMS]: 714

[ Synthesis Example  33] Synthesis of Compound 106

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4,6-diphenyl-2- (3- (4,4,5) of Preparation Example 3 , 5-Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was subjected to the same procedure as in <Step 2> of [Preparation 9], except that Compound 3.9 was prepared. g (yield 54%) was obtained.

[LCMS]: 713

[ Synthesis Example  34] Synthesis of Compound 108

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3- (4,4,5) of Preparation Example 3 Except for using, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed. 3.8 g (52% yield) were obtained.

[LCMS]: 713

[ Synthesis Example  35] Synthesis of Compound 110

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except that, the same procedure as in <Step 2> of [Preparation 9] was performed to obtain 4.7 g (yield 58%) of the title compound.

[LCMS]: 790

[ Synthesis Example  36] Synthesis of Compound 111

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 [Example of preparation except that 2-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used 9] was carried out in the same manner as in <Step 2>, to obtain 4.4 g (yield 55%) of the title compound.

[LCMS]: 789

[ Synthesis Example  37] Synthesis of Compound 116

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 6,8-diphenyl-2- (3- (4,4,5) of Preparation Example 3 [Preparation, except that, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine was used. The same procedure as in <Step 2> of Example 9] was carried out to obtain 3.4 g (yield 45%) of the title compound.

[LCMS]: 752

[ Synthesis Example  38] Synthesis of Compound 120

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], to obtain the target compound 3.9 g (yield 48%).

[LCMS]: 790

[ Synthesis Example  39] Synthesis of Compound 122

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, Preparation Example 9, except that 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) pyrimidine was used. ], 4.2 g (yield 52%) of the title compound were obtained in the same manner as in <Step 2>.

[LCMS]: 789

[ Synthesis Example  40] Synthesis of Compound 123

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 5.5 g (yield 62%) of the title compound was obtained in the same manner as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  41] Synthesis of Compound 124

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 2-phenyl-6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 5.1 g (yield 58%) of the title compound.

[LCMS]: 866

[ Synthesis Example  42] Synthesis of Compound 126

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 6,8-diphenyl-2- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl)-[1,2,4] triazolo [1 Except for using, 5-A] pyridine, the same procedure as in <Step 2> of [Preparation 9] was performed to obtain 4.0 g (yield 47%) of the title compound.

[LCMS]: 829

[ Synthesis Example  43] Synthesis of Compound 155

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 [Example of preparation except that 4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used 9] was carried out in the same manner as in <Step 2> to obtain 5.8 g (yield 72%) of the title compound.

[LCMS]: 789

[ Synthesis Example  44] Synthesis of Compound 157

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-di ([1,1'-biphenyl] -4- in Preparation Example 3 1) -6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 6.1 g (yield 69%) of the title compound was obtained.

[LCMS]: 867

[ Synthesis Example  45] Synthesis of Compound 158

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -3-yl) of Preparation Example 3 4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9] to give the target compound 5.1 g (yield 63%).

[LCMS]: 790

[ Synthesis Example  46] Synthesis of Compound 166

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] of Preparation Example 3 and 2-phenyl-4- (3- (4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) quinazoline was subjected to the same procedure as in <Step 2> of [Preparation 9] to give 4.1 g of the target compound (yield) 58%).

[LCMS]: 687

[ Synthesis Example  47] Synthesis of Compound 170

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4,4 '-(6- (3- (4,4,5, Except for using 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine-2,4-diyl) dibenzonitrile 4.2 g (yield 52%) of the title compound was obtained in the same manner as in <Step 2> of [Preparation Example 9].

[LCMS]: 764

[ Synthesis Example  48] Synthesis of Compound 185

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 [Example of preparation except that 2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used 9] was obtained in the same manner as in <Step 2>, to obtain 4.7 g (yield 58%) of the title compound.

[LCMS]: 789

[ Synthesis Example  49] Synthesis of Compound 186

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-di ([1,1'-biphenyl] -4- in Preparation Example 3 I) -6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], to obtain 4.9 g (yield 56%) of the title compound.

[LCMS]: 867

[ Synthesis Example  50] Synthesis of Compound 188

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-di (naphthalen-2-yl) -6- (4- in Preparation Example 3 [Preparation 9], except that (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. 4.0 g (yield 48%) of the title compound was obtained in the same manner as in <Step 2>.

[LCMS]: 814

[ Synthesis Example  51] Synthesis of Compound 199

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (2- (4,4,5) of Preparation Example 3 [Step 2] of [Preparation Example 9], except that, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. The same procedure was followed to obtain 3.0 g (yield 42%) of the title compound.

[LCMS]: 714

[ Synthesis Example  52] Synthesis of Compound 200

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except that, the same procedure as in <Step 2> of [Preparation Example 9] was carried out to obtain 3.7 g (yield 46%) of the title compound.

[LCMS]: 790

[ Synthesis Example  53] Synthesis of Compound 202

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 [Preparation example except that 2-phenyl-6- (2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used. 9] was carried out in the same manner as in <Step 2>, to obtain 3.5 g (yield 43%) of the title compound.

[LCMS]: 789

[ Synthesis Example  54] Synthesis of Compound 213

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-di ([1,1'-biphenyl] -4- in Preparation Example 3 Yl) -6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3- 6.7 g (yield 69%) of the title compound was obtained in the same manner as <Step 2> of [Preparation Example 9], except that 1) -1,3,5-triazine was used.

[LCMS]: 943

[ Synthesis Example  55] Synthesis of Compound 219

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 2- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) quina Except for using sleepy, 4.8 g (yield 56%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9].

[LCMS]: 840

[ Synthesis Example  56] Synthesis of Compound 224

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-di ([1,1'-biphenyl] -4- in Preparation Example 3 Yl) -6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4- 6.4 g (yield 72%) of the title compound was obtained in the same manner as <Step 2> of [Preparation Example 9], except that the one) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  57] Synthesis of Compound 229

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-phenyl-2- (3 '-(4,4,5,5) of Preparation Example 3 [Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) quinazoline except that < 4.9 g (yield 63%) of the title compound were obtained by the same procedure as in Step 2>.

[LCMS]: 763

[ Synthesis Example  58] Synthesis of Compound 239

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (4 '-(4,4, Preparation Example 9, except that 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) pyrimidine was used. ], The same procedure as in <Step 2> was obtained 5.5 g (yield 68%) of the title compound.

[LCMS]: 789

[ Synthesis Example  59] Synthesis of Compound 240

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 2-phenyl-6- (4 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 4.7 g (yield 53%) of the title compound.

[LCMS]: 866

[ Synthesis Example  60] Synthesis of Compound 242

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 6-phenyl-2- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 4.0 g (yield 45%) of the title compound.

[LCMS]: 866

[ Synthesis Example  61] Synthesis of Compound 245

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 3.8 g (yield 47%) of the title compound was obtained.

[LCMS]: 790

[ Synthesis Example  62] Synthesis of Compound 257

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 6,8-diphenyl-2- (2 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl)-[1,2,4] triazolo [1 Except for using, 5-e] pyrimidine, 3.2 g (yield 38%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9].

[LCMS]: 829

[ Synthesis Example  63] Synthesis of Compound 260

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 3.7 g (yield 42%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  64] Synthesis of Compound 266

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (4 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 4.4 g (yield 54%) of the title compound was obtained.

[LCMS]: 790

[ Synthesis Example  65] Synthesis of Compound 270

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 2-phenyl-6- (4 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 5.0 g (yield 57%) of the title compound.

[LCMS]: 866

[ Synthesis Example  66] Synthesis of Compound 279

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 3 2-phenyl-6- (4 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation 9] was performed to obtain 3.7 g (yield 42%) of the title compound.

[LCMS]: 866

[ Synthesis Example  67] Synthesis of Compound 280

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (4 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 3.1 g (yield 38%) of the title compound was obtained.

[LCMS]: 790

[ Synthesis Example  68] Synthesis of Compound 284

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4 3.9 g (yield 44%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  69] Synthesis of Compound 286

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4,6-diphenyl-2- (2 '-(4,4, [Preparation 9], except that 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) pyrimidine was used. 3.8 g (yield 47%) of the title compound were obtained in the same manner as in <Step 2>.

[LCMS]: 789

[ Synthesis Example  70] Synthesis of Compound 293

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 3 4-phenyl-6- (2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2 3.7 g (yield 42%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  71] Synthesis of Compound 295

2'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (2 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 3.6 g (yield 45%) of the title compound was obtained.

[LCMS]: 790

[ Synthesis Example  72] Synthesis of Compound 137

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3- (4,4,5) in Preparation Example 4 [Step 2] of [Preparation Example 9], except that, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine was used. The same procedure was followed to obtain 5.3 g (72% yield) of the title compound.

[LCMS]: 714

[ Synthesis Example  73] Synthesis of Compound 139

3'-Bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 4 4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9] to give the target compound 5.5 g (68% yield).

[LCMS]: 790

[ Synthesis Example  74] Synthesis of Compound 142

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) -1,3,5-triazine A target compound of 5.9 g (yield 73%) was obtained by the same procedure as in <Step 2> of [Preparation Example 9].

[LCMS]: 790

[ Synthesis Example  75] Synthesis of Compound 306

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3- (4,4,5) in Preparation Example 4 Except for using, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed. 4.7 g (65% yield) were obtained.

[LCMS]: 713

[ Synthesis Example  76] Synthesis of Compound 309

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 4 [Example of preparation except that 2-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used 9] was carried out in the same manner as in <Step 2>, to obtain 5.0 g (yield 62%) of the title compound.

[LCMS]: 789

[ Synthesis Example  77] Synthesis of Compound 312

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 6,8-diphenyl-2- (3- (4,4,5) of Preparation Example 4 [Preparation, except that, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine was used. 4.4 g (yield 58%) of the title compound was obtained in the same manner as <Step 2> of Example 9].

[LCMS]: 752

[ Synthesis Example  78] Synthesis of Compound 314

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4,6-diphenyl-2- (3 '-(4,4, Preparation Example 9, except that 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) pyrimidine was used. ], The same procedure as in <Step 2> to give the target compound 5.2 g (64% yield).

[LCMS]: 789

[ Synthesis Example  79] Synthesis of Compound 315

3'-Bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 4 4-phenyl-6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 6.1 g (yield 69%) of the title compound was obtained by the same procedure as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  80] Synthesis of Compound 316

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-([1,1'-biphenyl] -4-yl) of Preparation Example 4 2-phenyl-6- (3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 Except for using -yl) pyrimidine, the same procedure as in <Step 2> of [Preparation Example 9] was performed, to obtain 4.7 g (yield 53%) of the title compound.

[LCMS]: 866

[ Synthesis Example  81] Synthesis of Compound 319

3'-Bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 4-phenyl-2- (3 '-(4,4,5,5) of Preparation Example 4 Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3-yl) quinazoline except that < 3.7 g (yield 48%) of the title compound were obtained by the same procedure as in Step 2>.

[LCMS]: 763

[ Synthesis Example  82] Synthesis of Compound 321

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2,4-diphenyl-6- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) -1,3,5-triazine Except for the same procedure as in <Step 2> of [Preparation Example 9], 4.6 g (yield 57%) of the title compound was obtained.

[LCMS]: 790

[ Synthesis Example  83] Synthesis of Compound 324

3'-Bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 2-([1,1'-biphenyl] -4-yl) of Preparation Example 4 4-phenyl-6- (4 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -3 4.6 g (yield 52%) of the target compound were obtained by the same procedure as <Step 2> of [Preparation Example 9], except that -yl) -1,3,5-triazine was used.

[LCMS]: 867

[ Synthesis Example  84] Synthesis of Compound 330

3'-bromo-10-phenyl-10H-spiro [acridin-9,9'-fluorene] and 6,8-diphenyl-2- (3 '-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -2-yl)-[1,2,4] triazolo [1 3.8 g (yield 45%) of the title compound was obtained in the same manner as <Step 2> of [Preparation Example 9], except that, 5-A] pyridine was used.

[LCMS]: 829

Examples 1 to 18 Fabrication of Blue Organic Electroluminescent Devices

Compound 1, 4, 5, 8, 14, 20, 37, 52, 53, 59, 91, 97, 102, 114, 134, 136, 141, 147 synthesized in Synthesis Example in a high purity sublimation tablet Then, a blue organic electroluminescent device was produced as follows.

first. A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. 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 The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode (anode), DS-205 (hole transport layer) (Doosan Electronics, 80 nm) / NPB (hole transport auxiliary layer) (15 nm) / ADN + 5% DS-405 (light emitting layer) (Doosan Electronics, 30nm) / each compound shown in Table 1 (electron transport layer) (30 nm) / LiF (electron injection layer) (1 nm) / Al (cathode) (200 nm) laminated in the organic field A light emitting device was produced.

[ Comparative example  1] blue organic Electric field  Fabrication of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of compound 1 as an electron transporting material.

Comparative Example 2 Fabrication of Blue Organic Electroluminescent Device

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

The structures of NPB, AND and Alq ₃ used in Examples 1 to 18 and Comparative Examples 1 and 2 are as follows.

[Evaluation Example 1]

For the blue organic electroluminescent devices fabricated in Examples 1 to 18 and Comparative Examples 1 and 2, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.

Sample Electron transport layer Driving voltage (V) Light emitting peak (nm) Current efficiency (cd / A) Example 1 Compound 1 4.2 456 8.2 Example 2 Compound 4 3.7 452 8.5 Example 3 Compound 5 3.5 450 7.2 Example 4 Compound 8 3.5 452 8.8 Example 5 Compound 14 3.7 455 9.1 Example 6 Compound 20 3.8 452 8.5 Example 7 Compound 37 4.5 455 8.5 Example 8 Compound 52 4.5 455 7.8 Example 9 Compound 53 3.9 452 7.9 Example 10 Compound 59 3.6 455 8.2 Example 11 Compound 91 3.3 455 8.1 Example 12 Compound 97 3.4 458 8.5 Example 13 Compound 102 3.7 455 8.6 Example 14 Compound 114 4.2 456 8.0 Example 15 Compound 134 4.1 455 8.9 Example 16 Compound 136 3.9 458 8.5 Example 17 Compound 141 3.8 455 7.2 Example 18 Compound 147 4.0 456 7.5 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent device (Examples 1 to 18) using the compound of the present invention in the electron transporting layer is a blue organic electroluminescent device (comparative example 1) using Alq ₃ in the electron transporting layer and Compared with the blue organic electroluminescent device (Comparative Example 2) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.

Examples 19 to 79 Fabrication of Blue Organic Electroluminescent Devices

Compound 5 to compound 330 synthesized in the Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was manufactured according to the following procedure.

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, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode (anode), DS-205 (hole transporting layer) (Doosan Electronics 80 nm) / NPB (hole transporting auxiliary layer) (15 nm) / ADN + 5% DS-405 (light emitting layer) ( Doosan Corporation, 30 nm) / Each compound (electron transport auxiliary layer) (5 nm) / Alq ₃ (electron transport layer) (25 nm) / LiF (electron injection layer) (1 nm) / Al ( (Electrode) (200 nm) in order to manufacture an organic electroluminescent device.

Comparative Example 3 Fabrication of Blue Organic Electroluminescent Device

Without the use of Compound 5 as the electron transporting the secondary layer material, and has, in the same way as in Example 19 except for depositing the Alq ₃ electron transporting material to 30 nm instead of 25 nm to prepare a blue organic light emitting element .

[Evaluation Example 2]

For the organic electroluminescent devices manufactured in Examples 19 to 78 and Comparative Example 3, the driving voltage, the light emission wavelength, 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 Electron transport auxiliary layer Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 19 Compound 5 4.2 456 8.2 Example 20 Compound 6 3.9 450 7.5 Example 21 Compound 18 3.6 452 7.8 Example 22 Compound 22 3.8 455 7.9 Example 23 Compound 31 3.6 458 8.4 Example 24 Compound 37 3.9 458 8.0 Example 25 Compound 44 4.0 450 7.8 Example 26 Compound 56 4.2 452 7.9 Example 27 Compound 70 4.5 455 8.5 Example 28 Compound 82 3.9 456 8.2 Example 29 Compound 118 3.3 458 9.1 Example 30 Compound 128 4.2 455 7.5 Example 31 Compound 145 4.3 456 7.8 Example 32 Compound 149 3.9 458 8.5 Example 33 Compound 104 3.8 459 8.1 Example 34 Compound 106 3.9 459 8.2 Example 35 Compound 108 3.9 459 8.0 Example 36 Compound 110 3.8 455 8.3 Example 37 Compound 111 4.0 460 8.1 Example 38 Compound 114 4.1 458 7.8 Example 39 Compound 116 4.1 454 7.9 Example 40 Compound 120 4.4 455 7.2 Example 41 Compound 122 3.4 456 8.5 Example 42 Compound 123 3.3 458 8.7 Example 43 Compound 124 3.6 455 9.0 Example 44 Compound 126 3.3 456 8.8 Example 45 Compound 155 4.0 457 8.0 Example 46 Compound 157 3.9 458 8.2 Example 47 Compound 158 3.9 457 8.2 Example 48 Compound 166 4.2 457 7.8 Example 49 Compound 170 4.2 458 7.8 Example 50 Compound 185 4.6 458 6.9 Example 51 Compound 186 4.5 458 7.0 Example 52 Compound 199 4.5 456 7.2 Example 53 Compound 200 4.4 456 7.1 Example 54 Compound 213 3.5 459 8.5 Example 55 Compound 219 3.4 459 8.9 Example 56 Compound 229 4.5 456 7.4 Example 57 Compound 240 4.6 458 7.5 Example 58 Compound 242 3.8 459 8.1 Example 59 Compound 245 3.9 457 7.9 Example 60 Compound 257 3.7 458 8.0 Example 61 Compound 266 4.3 456 7.0 Example 62 Compound 279 4.4 459 7.2 Example 63 Compound 280 4.5 458 7.3 Example 64 Compound 286 4.4 457 7.1 Example 65 Compound 295 4.2 456 7.5 Example 66 Compound 137 4.3 457 7.0 Example 67 Compound 139 4.4 457 7.2 Example 68 Compound 142 3.9 458 8.0 Example 69 Compound 306 4.4 458 7.3 Example 70 Compound 309 4.5 458 7.0 Example 71 Compound 312 4.5 456 7.5 Example 72 Compound 314 4.1 456 7.5 Example 73 Compound 315 4.2 456 7.9 Example 74 Compound 316 4.0 457 7.6 Example 75 Compound 319 4.1 458 7.8 Example 76 Compound 321 4.6 459 6.8 Example 77 Compound 324 4.6 459 6.9 Example 78 Compound 330 4.5 459 7.1 Example 79 Compound 97 4.7 459 6.7 Comparative Example 3 - 4.8 458 6.0

As shown in Table 2, the blue organic electroluminescent devices (Examples 19 to 79) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, light emission peak, and driving voltage.

In particular, in the case of including the phenylene or biphenylene linker as in Examples 19 to 78, the current efficiency is higher than the compound 97 without the linker (Example 79), the driving voltage shows a lower performance I could see that. In other words, when a linker of phenyl or biphenyl is present in the compound used as the electron transport auxiliary layer, the band gap is widened due to the increase in the LUMO level of the material, which increases the current efficiency and further lowers the driving voltage, which is more preferable.

In addition, in the moiety of spirofluorene xanthene or spiroacridine fluorene as in Examples 29, 41 to 44, 54 and 55, a substituent is connected to position 2 of the fluorene-type core at other positions. It was found that the current efficiency was higher and the driving voltage had lower performance than when the substituents were connected (Examples 68, 73 to 75).

[Description of the code]

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

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 (21)

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

In Chemical Formula 1, X is O or N (Ar ₂ ); l, m and n are each independently an integer from 0 to 4; o is an integer from 0 to 3; Ar ₁ and Ar ₂ 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; R ₁ to R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 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, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C _{60 It} is selected from the group consisting of arylamine group, when each of the R ₁ to R ₄ plural are the same as each other or Different; L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms; The arylene group and the heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of Ar ₁ , Ar ₂ and R ₁ to R ₄ , 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, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ of the Aryloxy group of -C ₆₀ , C ₁ -C ₄₀ alkyloxy group, arylamine group of C ₆ -C ₆₀ , cycloalkyl group of C ₃ -C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine blood When substituted or unsubstituted with one or more substituents selected from the group consisting of a nilyl group and a C ₆ -C ₆₀ arylsilyl group, and substituted with a plurality of substituents, they may be the same or different from each other, At least one of Ar ₂ and R ₁ to R ₄ is a substituent represented by Formula 2; [Formula 2]

In Chemical Formula 2, * Means the part where the bond is made; L ₃ and L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms; Ar ₃ 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; The arylene group and heteroarylene group of L ₃ and L ₄ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of Ar ₃ Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C 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 substituted by one or more substituents selected from the group consisting of a reel, or silyl which is Beach ring, substituted with a plurality of substituents, they may be the same or different from each other. The method of claim 1, The compound is a compound represented by the formula [Formula 3]

In Chemical Formula 3, L ₁ , L ₂ , R ₁ to R ₃ , Ar ₁ , l, m and n are each as defined in claim 1. The method of claim 1, The compound is a compound represented by the following formula 4 or 5: [Formula 4]

[Formula 5]

In Chemical Formulas 4 and 5, L ₁ , L ₂ , R ₁ to R ₃ , Ar ₁ , l, m and n are each as defined in claim 1. The method of claim 3, The compound is represented by the formula (4). The method of claim 1, Ar ₁ is a compound represented by Formula 6 below: [Formula 6]

In Chemical Formula 6, * Means the part where the bond is made; Z ₁ to Z ₅ are each independently N or C (R ₅ ), but at least one of Z ₁ to Z ₅ is N; R ₅ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ arylamine 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 phospha Or a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylsilyl group or combine with an adjacent group to form a condensed ring, wherein R ₅ is a plurality of If they are the same or different from one another; The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R ₅ , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. The method of claim 1, Ar ₁ is a compound represented by Formula 7 below: [Formula 7]

In Chemical Formula 7, * Means the part where the bond is made; Y ₁ to Y ₃ are each independently N or C (R ₇ ), but at least one of Y ₁ to Y ₃ is N; Y ₄ is N (R ₈ ) or C (R ₉ ) (R ₁₀ ); R ₇ to R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to C ₆₀ aryl phosphazene group, selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ with an aryl silyl group of C _60, or combine tile adjacent to which they are attached may form a fused ring, When there are a plurality of R ₇ , they are the same or different from each other; The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₇ to R ₁₀ 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 of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. The method of claim 5, The substituent represented by Formula 6 is a compound represented by any one of the following formula A-1 to A-15:

In Chemical Formulas A-1 to A-15, p is an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 2 R ₆ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, When C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylsilyl group selected from the group or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R ₆ They are the same or different from each other; Alkyl group of the R _6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, these are the same or may be different from one another, and; * And each R ₅ is as defined in claim 5. The method of claim 6, The substituent represented by Formula 7 is a compound represented by any one of the following formulas B-1 to B-11:

In Chemical Formulas B-1 to B-11, s is an integer from 0 to 2; t is an integer from 0 to 4; R ₁₁ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl 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 ~ C _{60 It} is selected from the group consisting of mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R ₁₁ They are Same or different from each other; Alkyl group of the R _11, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron 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, 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, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ At least one member selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diaryl phosphinyl group, and a C ₆ to C ₆₀ arylsilyl group When unsubstituted or substituted with a substituent, and substituted with a plurality of substituents, they may be the same as or different from each other; *, R ₇ to R ₁₀ are each as defined in claim 6. The method of claim 1, Compound represented by Formula 1 is a compound represented by any one of the following formulas 8 to 12: [Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 8 to 12, p and t are each independently an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 2; R ₅ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ arylamine 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 phospha A aryl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group, or combine with an adjacent group to form a condensed ring; R ₆ and R ₁₁ 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 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to C ₆₀ An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R _{When 6} and R ₁₁ are each plural, they are the same as 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 of R ₅ , R ₆ and R ₁₁ 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 alkyl group, C ₂ ~ C ₄₀ alkenes group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C _60, alkyloxy group of C ₁ ~ C ₄₀ of the , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group , C group ₆ to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphazene group, C ₆ to C ₆₀ mono or diaryl phosphine blood group and a C ₆ to line from the group consisting of C ₆₀ aryl silyl A substituted or unsubstituted by one or more substituent species, when it is substituted with a plurality of substituents, these are the same or may be different from one another, and; X, l, m, n, R ₁ , R ₂ , R ₃ , L ₁ and L ₂ are each as defined in claim 1. The method of claim 1, L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group, and a carbazolyl group. The method of claim 1, L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group. The method of claim 11, L ₁ and L ₂ may be each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group, but both L ₁ and L ₂ are not a single bond. The method of claim 1, Wherein L ₁ and L ₂ are each independently a single bond or a linker represented by any one of Formulas C-1 to C-12:

In Chemical Formulas C-1 to C-12, * Means the part where the coupling is made. The method of claim 13, L ₁ and L ₂ are each independently a single bond or a linker represented by any one of the formula C-2, C-3, C-7, C-8, C-9, C-10 and C-11, And both L ₁ and L ₂ are not single bonds. The method of claim 1, At least one of the R ₁ to R ₃ is a compound selected from the group consisting of halogen, cyano group and C ₆ ~ C ₆₀ aryl group. The method of claim 5, R ₅ is selected from the group consisting of hydrogen, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group, When the alkyl group, aryl group and heteroaryl group of R ₅ are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano group and C ₆ ~ C ₆₀ aryl group, and substituted with a plurality of substituents , These are the same or different compounds from each other. The method of claim 6, R ₇ to R ₁₀ are each independently selected from the group consisting of hydrogen, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a nuclear atom having 5 to 60 heteroaryl groups, The alkyl group, aryl group and heteroaryl group of R ₇ to R ₁₀ are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano group and C ₆ ~ C ₆₀ aryl group, a plurality of substituents When substituted, they are the same or different from each other. The method of claim 1, Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of:

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 19, The organic 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. The method of claim 19, The organic material layer including the compound is an organic electroluminescent device selected from the group consisting of a light emitting layer, an electron transport layer and an electron transport auxiliary layer.

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