KR20150008678A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescence device comprising the same. According to the present invention, the compound is used to an organic material layer of the organic electroluminescence device, desirably to a light emitting layer, thereby improving light emitting efficiency, driving voltage, lifespan, etc of the organic electroluminescence device. To this end, the compound is represented by chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity of Bernanose in the 1950s . In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to their low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and having improved driving voltage, luminous efficiency, and the like.

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

X ₁ to X ₅ are the same or different and each independently N or CR _1, wherein at least one of X ₁ to X ₅ is N,

In this case, when the CR ₁ in plurality, R ₁ is the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups of binding to the the To form a condensed ring,

L is a single bond or a phenylene group or a biphenylene group,

R ₂ to R ₉ Are the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ to each other - a heteroaryl group of C ₄₀ aryl group, the number of nuclear atoms of 5 to 40, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _40, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of a silyl or, the groups bonded to adjacent or may form a condensed ring,

에서 선택된다.R₁₁ And R₁₂ Is a methyl group, a phenyl group, or an adjacent phenyl group is bonded to form a spy

.

In the above R ₁ to R ₉ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ The arylphosphine oxide group and the C ₆ to C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl yarn Of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of And arylsilyl group, and when a plurality of substituents are introduced, these substituents may be the same as or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the general formula A light emitting device is provided.

At least one of the organic layers including the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer. Preferably, The compound represented by the formula (1) is a blue, green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time, A full-color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention has a structure in which an indenoindole moiety having heterocycle bonded thereto containing at least one N atom forms a basic skeleton and various substituents are bonded to the basic skeleton. . The compound of the present invention has both an electron withdrawing group (EWG) having a large electron absorbing property and an electron donating group (EDG) having an electron donating property, and the whole molecule has a bipolar characteristic. And bonding of electrons can be enhanced. Therefore, it is not only advantageous as a host in the phosphorescent light-emitting layer but also can be applied to a hole transport layer, a hole injection layer, and the like.

In addition, compound molecules are distorted by substituting methyl or phenyl at the 10-position of the indenoindole moiety or by binding in the form of spies, thereby solving the problem of degradation in luminescence properties due to pi-pi stacking Thereby preventing the formation of an excimer, thereby improving the luminous efficiency.

Also, in the phosphorescent light-emitting layer, the host material should have a higher triplet energy gap of the host than the dopant, because the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant to provide effective phosphorescence from the dopant. In Table 1, the compound of the present invention has a triplet energy value of 2.38 to 2.54, and thus has a triplet energy suitable for phosphorescence emission.

Calculated value B3LYP / 6-31G * PGH rescue HOMO calculation LUMO calculation Band gap calculation S1 T1 S1-T1 Dipole moment
(Debye) Total energy PGH_DPII_1

-5.011 -1.973 3.038 2.598 2.522 0.076 1.6127 -1680 PGH_DPII_2

-5.214 -1.960 3.254 2.740 2.415 0.325 1.3403 -1680 PGH_DPII_3

-5.073 -1.988 3.085 2.645 2.535 0.109 1.9645 -1920 PGH_DPII_4

-5.017 -1.940 3.077 2.630 2.541 0.089 0.7565 -2430 PGH_DPII_5

-5.056 -1.997 3.059 2.621 2.518 0.104 2.1580 -2070 PGH_DPII_6

-5.203 -1.976 3.228 2.717 2.387 0.330 1.5733 -1840 PGH_DPII_7

-5.024 -1.998 3.026 2.594 2.508 0.086 2.1042 -2070 PGH_DPII_8

-5.170 -1.971 3.199 2.695 2.382 0.312 1.4827 -1840

On the other hand, since the molecular weight of the compound is significantly increased due to the aromatic ring or the heteroaromatic ring substituent introduced into the compound, the glass transition temperature is improved, and thus, compared with the conventional CBP (4,4-dicarbazolylbiphenyl) And exhibits high thermal stability. Further, the compound represented by the general formula (1) of the present invention is also effective for inhibiting crystallization of the organic material layer.

As described above, when the compound of Formula 1 according to the present invention is used as a hole injecting / transporting layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, compared to a conventional organic layer material (for example, CBP) The efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

In the compound represented by the general formula (1), X ₁ to X ₅ are the same as or different from each other, and each independently N or CR _1, wherein at least one of X ₁ to X ₅ is N.

In this case, when the CR ₁ in plurality, R ₁ may be the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups of binding to the the To form a condensed ring.

는 하기 구조에서 선택될 수 있다.Preferably,

Can be selected from the following structures.

In the above structural formula, R1 is as defined in the above formula (1) and L is a single bond or a phenylene group or a biphenylene group.

(a) is an integer of 0 to 4, provided that when R ₁₀ is plural, R ₁₀ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, an aryloxy group of a heteroaryl group of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to _40, C ₆ ~ C 40 of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ of C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ group consisting arylsilyl of Or may combine with adjacent groups to form a condensed ring.

R ₂ to R ₉ Are the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ to each other - a heteroaryl group of C ₄₀ aryl group, the number of nuclear atoms of 5 to 40, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _40, C ₆ - combine C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of a silyl or, or adjacent groups which may form a condensed ring.

Preferably, R ₂ to R ₉ Are each independently selected from hydrogen, a C ₆ to C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms, or may be bonded to adjacent groups to form a condensed ring.

More preferably R ₂ to R ₉ Are independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group, and a substituent represented by the following formula (6), preferably R ₂ to R ₉ Are all hydrogen.

Y ₁ is selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine pingi, are selected from the aryl phosphine oxide group, and the group consisting of a C ₆ ~ C ₄₀ aryl silyl group of C ₆ ~ C _40.

R ₁ to R ₁₀ And Ar ₁ to Ar _{5 each} independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ The arylphosphine oxide group and the C ₆ to C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl Of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of And an arylsilyl group. When a plurality of substituents are introduced at this time, these substituents may be the same as or different from each other.

More specifically, the compound represented by the formula (1) of the present invention can be represented by the following formulas (2) to (4).

In formulas (2) to (4)

X ₁ to X ₅ , R ₂ to R ₉ And L are each as defined in the above formula (1).

More specific examples of the compound represented by the formula (1) include compounds consisting of the following C 1 to C 216, but are not limited thereto.

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

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

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

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

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . &Lt; / RTI &gt; 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 40 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls 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 a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

The "fused 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 compounds of formula (1) of the present invention can be synthesized in various ways with reference to the following Synthesis Examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

<Organic Field  Light emitting element>

The present invention provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1), preferably the compound represented by any one of the formulas (2) to (5).

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ Preferably, the organic compound layer containing the compound of Formula 1 may be a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

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

[ Preparation Example  One] DHII Synthesis of -1

(12.8 g, 80.0 mmol), phenylhydrazine (12.72 g, 88.0 mmol) and AcOH (128 ml) were placed in a 250 ml three-necked flask, Lt; / RTI &gt; After completion of the reaction, and to remove the AcOH and extracted with methylene chloride and the filter into the MgSO _4. After removing the solvent of the filtered organic layer, DHII-1 (11.9 g, 51.1 mmol, yield 64%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 233 g / mol

Elemental Analysis: C, 87.52; H, 6.48; N, 6.00

^{1 H-NMR: δ1.72 (s} , 6H), 6.95 (m, 2H), 7.32 (m, 3H), 7.62 (m, 2H), 7.94 (d, 1H), 11.37 (s, 1H)

[ Preparation Example  2] DHII Synthesis of -2

<Step 1> 8- bromo -10,10- dimethyl -5,10- dihydroindeno Synthesis of [1,2-b] indole

bromo-10,10-dimethyl-5,10-dihydroindeno [1,2] benzodiazepine was prepared by following the same procedure as described in Preparation Example 1, except using (4-bromophenyl) hydrazine (20.5 g, 88.0 mmol) -b] indole (15.7 g, 50.5 mmol, yield 63%).

Mass: [M] &lt; ⁺ & gt ^; = 311 g / mol

Elemental Analysis: C, 65.40; H, 4.52; Br, 25.59; N, 4.49

<Step 2> DHII Synthesis of -2

(15.6 g, 50.0 mmol), phenylboronic acid (9.14 g, 75.0 mmol) and NaOH (6.0 g, 150.0 mmol) were added under nitrogen stream under nitrogen atmosphere. mmol) and THF / H ₂ O (250 ml / 120 ml) were added and stirred. Pd (PPh ₃ ) ₄ (2.89 g, 5 mol%) was added thereto at 40 ° C, and the mixture was stirred at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, DHII-2 (11.1 g, 36.1 mmol, yield 72%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 309 g / mol

Elemental Analysis: C, 89.28; H, 6.19; N, 4.53

^{1 H-NMR: δ1.72 (s} , 6H), 7.33 (m, 3H), 7.51 (m, 5H), 7.65 (m, 2H), 7.74 (d, 1H), 7.96 (s, 1H), 11.37 (s, 1 H)

[ Preparation Example  3] DHII Synthesis of -3

(13.3 g, 34.5 mmol, yield 69%) was obtained in the same manner as Step 2 of Preparation Example 2 except that biphenyl-3-ylboronic acid (14.9 g, 75.0 mmol) ).

Mass: [M] &lt; ⁺ & gt ^; = 385 g / mol

Elemental Analysis: C, 90.35; H, 6.01; N, 3.63

^{1 H-NMR: δ1.72 (s} , 6H), 7.34 (m, 3H), 7.45 (m, 3H), 7.52 (m, 5H), 7.64 (m, 2H), 7.72 (m, 2H), 7.95 (s, 1 H), 11.36 (s, 1 H)

[ Preparation Example  4] DHII Synthesis of -4

(17.5 g, 75.0 mmol) was used in the same manner as Step 2 of Preparation Example 2 except that 9-phenyl-9H-carbazol-3-ylboronic acid (21.5 g, 37.0 mmol, yield 74%).

Mass: [M] &lt; ⁺ & gt ^; = 474 g / mol

Elemental Analysis: C, 88.58; H, 5.52; N, 5.90

^{1 H-NMR: δ1.73 (s} , 6H), 7.32 (m, 4H), 7.45 (t, 1H), 7.53 (m, 5H), 7.62 (m, 3H), 7.74 (m, 2H), 7.99 (m, 2 H), 8.13 (m, 2 H), 11.34 (s, 1 H)

[ Preparation Example  5] DHII Synthesis of -5

(16.4 g, 75.0 mmol) was used in the same manner as in <Step 2> of Preparation Example 2 except that dibenzo [b, d] thiophen-4-ylboronic acid (17.1 g, 39.7 mmol, yield 79%).

Mass: [M] &lt; ⁺ & gt ^; = 415 g / mol

Elemental Analysis: C, 83.82; H, 5.09; N, 3.37; S, 7.72

^{1 H-NMR: δ1.72 (s} , 6H), 7.32 (m, 3H), 7.52 (m, 3H), 7.62 (m, 2H), 7.73 (d, 1H), 7.97 (m, 2H), 8.20 (d, IH), 8.43 (m, 2H), 11.36 (s, IH)

[ Preparation Example  6] DHII Synthesis of -6

1,3-diphenyl-2,3-dihydro-1H-inden-1-one (22.7 g, 80.0 mmol) was used instead of 3,3-dimethyl-2,3-dihydro-1H- inden- (17.7 g, 49.6 mmol, yield 62%) was obtained in the same manner as in <Step 1> of Preparation Example 1, except that

Mass: [M] &lt; ⁺ & gt ^; = 357 g / mol

Elemental Analysis: C, 90.72; H, 5.36; N, 3.92

^{1 H-NMR: δ6.93 (m} , 2H), 7.12 (m, 4H), 7.28 (m, 4H), 7.33 (m, 5H), 7.63 (m, 2H), 7.94 (d, 1H), 11.36 (s, 1 H)

[ Preparation Example  7] DHII Synthesis of -7

<Step 1> 8- bromo -10,10- 피덴 -5,10- dihydroindeno Synthesis of [1,2-b] indole

1,3-diphenyl-2,3-dihydro-1H-inden-1-one (22.7 g, 80.0 mmol) was used instead of 3,3-dimethyl-2,3-dihydro-1H- inden- Bromo-10,10-diphenyl-5,10-dihydroindeno [1,2-b] indole (21.4 g, 49.1 mmol, yield 61%) was prepared in the same manner as Step 1 of Preparation Example 2, ).

Mass: [M] &lt; ⁺ & gt ^; = 436 g / mol

Elemental Analysis: C, 74.32; H, 4.16; Br, 18.31; N, 3.21

<Step 2> DHII Synthesis of -7

8-bromo-10,10-diphenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g, 10 mmol) instead of 8-bromo-10,10- , 50.0 mmol), DHII-7 (25.4 g, 42.5 mmol, yield 85%) was obtained.

Mass: [M] &lt; ⁺ & gt ^; = 598 g / mol

Elemental Analysis: C, 90.27; H, 5.05; N, 4.68

^{1 H-NMR: δ7.12 (m} , 4H), 7.32 (m, 10H), 7.46 (m, 5H), 7.68 (m, 6H), 7.97 (m, 2H), 8.12 (d, 1H), 8.18 (d, 1 H), 11.36 (s, 1 H)

[ Preparation Example  8] DHII Synthesis of -8

(2'H) -one (22.6 g, 80.0 mmol) instead of 3,3-diphenyl-2,3-dihydro-1H- inden- (17.7 g, 49.7 mmol, yield 63%) was obtained in the same manner as in <Step 1> of Preparation Example 6,

Mass: [M] &lt; ⁺ & gt ^; = 355 g / mol

Elemental Analysis: C, 91.24; H, 4.82; N, 3.94

¹ H-NMR:? 6.92 (m, 2H), 7.28 (m, 4H), 7.35 (m, 3H), 7.55 (m, 3 H), 11.36 (s, 1 H)

[ Preparation Example  9] DHII Synthesis of -9

&Lt; Step 1 > 8'- bromo -5 ' H- spiro [ 불소 -9,10'- indeno [1,2-b] indole]

(2'H) -one (22.6 g, 80.0 mmol) instead of 3,3-diphenyl-2,3-dihydro-1H- inden- Bromo-5'H-spiro [fluorene-9,10'-indeno [1,2-b] indole] (21.0 g, , 49.0 mmol, yield 60%).

Mass: [M] &lt; ⁺ & gt ^; = 434 g / mol

Elemental Analysis: C, 74.66; H, 3.71; Br, 18.40; N, 3.22

<Step 2> DHII Synthesis of -9

Bromo-5'H-spiro [fluorene-9,10'-indeno [1,2-b] indole instead of 8-bromo-10,10-diphenyl-5,10- dihydroindeno [ (25.1 g, 42.3 mmol, yield 84%) was obtained by following the procedure of <Step 2> of Preparation Example 7, except that the indole compound (21.8 g, 50.0 mmol)

Mass: [M] &lt; ⁺ & gt ^; = 596 g / mol

Elemental Analysis: C, 90.58; H, 4.73; N, 4.69

^{1 H-NMR: δ7.11 (m} , 4H), 7.33 (m, 8H), 7.47 (m, 4H), 7.68 (m, 7H), 7.97 (m, 2H), 8.11 (d, 1H), 8.20 (d, 1 H), 11.36 (s, 1 H)

[ Synthetic example  1] Synthesis of C 4

(2.33 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF 50 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain the target compound C 4 (4.06 g, yield 87%).

LC-Mass: 466 g / mol

[ Synthetic example  2] Synthesis of C 8

(2.33 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd ₂ (dba) ₃ 0.46 g, 0.5 mmol), ( t-Bu) 3 P (0.40 g, 2.0 mmol), put the sodium tert-butoxide (2.88 g, 30.0 mmol) in toluene (50 ml) was stirred at 110 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removal of the solvent of the filtered organic layer, the desired compound C 8 (4.12 g, yield 76%) was obtained by column chromatography.

LC-Mass: 542 g / mol

[ Synthetic example  3] Synthesis of C 31

The procedure of Synthesis Example 1 was repeated, except that DHII-2 (3.09 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C31 (4.79 g, yield 88%).

LC-Mass: 543 g / mol

[ Synthetic example  4] Synthesis of C 32

The procedure of Synthetic Example 2 was repeated except that DHII-2 (3.09 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C32 (4.64 g, yield 75%).

LC-Mass: 619 g / mol

[ Synthetic example  5] Synthesis of C 35

(5.26 g, yield 85%) was obtained in the same manner as in Synthesis Example 1, except that DHII-3 (3.86 g, 10.00 mmol) was used instead of DHII-1.

LC-Mass: 619 g / mol

[ Synthetic example  6] Synthesis of C 36

The procedure of Synthesis Example 2 was repeated except that DHII-3 (3.86 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C36 (4.93 g, yield 71%).

LC-Mass: 695 g / mol

[ Synthetic example  7] Synthesis of C 60

The procedure of Synthesis Example 1 was repeated except that DHII-4 (4.75 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C60 (5.73 g, yield 81%).

LC-Mass: 708 g / mol

[ Synthetic example  8] Synthesis of C 64

The procedure of Synthesis Example 2 was repeated except that DHII-4 (4.75 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C64 (5.41 g, yield 69%).

LC-Mass: 784 g / mol

[ Synthetic example  9] Synthesis of C 100

The procedure of Synthesis Example 1 was repeated except that DHII-5 (4.16 g, 10.00 mmol) was used instead of DHII-1 to obtain C 100 (5.26 g, yield 81%) as a target compound.

LC-Mass: 649 g / mol

[ Synthetic example  10] Synthesis of C 103

The procedure of Synthesis Example 2 was repeated except that DHII-5 (4.16 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C 103 (5.37 g, yield 74%).

LC-Mass: 725 g / mol

[ Synthetic example  11] Synthesis of C 24

Synthesis was carried out except that 4- (biphenyl-4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used instead of 2- (3-chlorophenyl) -4,6- diphenyl- The procedure of Example 2 was repeated to obtain the target compound C24 (2.84 g, yield 55%).

LC-Mass: 516 g / mol

[ Synthetic example  12] Synthesis of C 25

2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl- (3.34 g, yield 59%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that the compound C 25 (3.34 g, yield: 59%) was obtained.

LC-Mass: 566 g / mol

[ Synthetic example  13] Synthesis of C 27

2- (3-chlorophenyl) -4- (4- (naphthalen-1-yl) phenyl) quinazoline (5.32 g, 12.00) instead of 2- (3- chlorophenyl) -4,6- diphenyl- mmol), the target compound C 27 (3.66 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 2.

LC-Mass: 642 g / mol

[ Synthetic example  14] Synthesis of C 53

(3.72 g, yield 58%) was obtained in the same manner as in Synthesis Example 12, except that DHII-2 (3.09 g, 10.00 mmol) was used instead of DHII-1.

LC-Mass: 642 g / mol

[ Synthetic example  15] Synthesis of C 112

The procedure of Synthetic Example 2 was repeated except that DHII-6 (3.57 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C 112 (4.92 g, yield 74%).

LC-Mass: 665 g / mol

[ Synthetic example  16] Synthesis of C 129

The procedure of Synthetic Example 12 was repeated, except that DHII-6 (3.57 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C 129 (3.92 g, yield 57%).

LC-Mass: 688 g / mol

[ Synthetic example  17] Synthesis of C 136

The procedure of Synthesis Example 1 was repeated except that DHII-7 (5.99 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C 136 (7.14 g, yield 86%).

LC-Mass: 830 g / mol

[ Synthetic example  18] Synthesis of C 157

The procedure of Synthesis Example 12 was repeated except that DHII-7 (5.99 g, 10.00 mmol) was used instead of DHII-1 to obtain the target compound C 157 (5.02 g, yield 54%).

LC-Mass: 929 g / mol

[ Synthetic example  19] Synthesis of C 168

The procedure of Synthesis Example 2 was repeated except that DHII-8 (3.55 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C 168 (4.71 g, yield 71%).

LC-Mass: 663 g / mol

[ Synthetic example  20] Synthesis of C 185

The procedure of Synthetic Example 12 was repeated except that DHII-8 (3.55 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C 185 (3.50 g, yield 51%).

LC-Mass: 686 g / mol

[ Synthetic example  21] Synthesis of C 192

The procedure of Synthetic Example 1 was repeated except that DHII-9 (5.97 g, 10.00 mmol) was used instead of DHII-1 to obtain the desired compound C 192 (7.37 g, yield 89%).

LC-Mass: 828 g / mol

[ Synthetic example  22] Synthesis of C 213

(5.19 g, yield 56%) was obtained in the same manner as in Synthesis Example 12, except that DHII-9 (5.97 g, 10.00 mmol) was used instead of DHII-1.

LC-Mass: 927 g / mol

[ Example  1 ~ 14] Green organic EL  Device fabrication

Compounds C 4 to C 192 synthesized in Synthesis Examples 1 to 14 were subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) thin film having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / each compound of C 4 to C 192 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) in this order to form an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP are as follows.

[ Comparative Example  1] Green organic EL  Device fabrication

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound C 4 as a luminescent host material in forming the light emitting layer.

The structure of CBP used is as follows.

[ Evaluation example ]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm2 were measured for each of the green organic EL devices manufactured in Examples 1 to 14 and Comparative Example 1, and the results are shown in Table 2 below .

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 C 4 6.72 517 40.9 Example 2 C 8 6.87 516 41.4 Example 3 C 31 6.49 518 38.9 Example 4 C 32 6.81 518 39.1 Example 5 C 35 6.78 517 39.1 Example 6 C 36 6.83 517 41.1 Example 7 C 60 6.82 518 40.7 Example 8 C 64 6.66 516 39.8 Example 9 C 100 6.71 518 39.1 Example 10 C 103 6.76 517 39.3 Example 11 C 112 6.72 518 38.5 Example 12 C 136 6.87 517 39.1 Example 13 C 168 6.66 517 41.1 Example 14 C 192 6.71 518 42.2 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 2, when the compound (C 4 to C 192) according to the present invention was used as a light emitting layer of a green organic EL device (Examples 1 to 14), a green organic EL device (Comparative Example 1 ), It can be seen that it shows better performance in terms of efficiency and driving voltage.

[ Example  15-22] Red organic EL  Device manufacturing

The compounds C 24, C 25, C 27, C 53, C 129, C 157, C 185, and C 213 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, Respectively.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / compound of each of C 24, C 25, C 27, C 53, C 129, C 157, C 185 and C 213 on the ITO transparent electrode thus prepared + 10% by _{piq) 2 Ir (acac) (} 300nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were sequentially stacked by making an organic electroluminescent device.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir (acac) and BCP used are as follows.

[ Comparative Example  2] Red organic EL  Device fabrication

A red organic electroluminescent device was fabricated in the same manner as in Example 15, except that CBP was used in place of the compound C 24 as a luminescent host material in forming the light emitting layer.

The structure of CBP used is as follows.

[ Evaluation example ]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 15 to 22 and Comparative Example 2, and the results are shown in Table 3 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 15 C 24 4.99 13.0 Example 16 C 25 5.12 11.4 Example 17 C 27 5.09 11.2 Example 18 C 53 4.88 12.2 Example 19 C 129 5.11 12.0 Example 20 C 157 5.20 9.8 Example 21 C 185 5.16 10.2 Example 22 C 213 4.99 11.5 Comparative Example 2 CBP 5.25 8.2

As shown in Table 3, when the compound according to the present invention was used as the material of the light emitting layer of the red organic electroluminescent device (Examples 15 to 22), the red light emitting device using the conventional CBP as the material of the light emitting layer 2), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

Claims (7)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X ₁ to X ₅ are the same or different and each independently N or CR _1, wherein X ₁ to X ₅ At least one of them is N,
In this case, when the CR ₁ in plurality, R ₁ is the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups of binding to the the To form a condensed ring,
L is a single bond or a phenylene group or a biphenylene group,
R ₂ to R ₉ Are the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ to each other - a heteroaryl group of C ₄₀ aryl group, the number of nuclear atoms of 5 to 40, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _40, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of a silyl or, the groups bonded to adjacent or may form a condensed ring,
R ₁₁ and R ₁₂ Is a methyl group, a phenyl group, or an adjacent phenyl group is bonded to form a spy

Lt; / RTI &gt;
In the above R ₁ to R ₉ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ The arylphosphine oxide group and the C ₆ to C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl yarn Of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of And arylsilyl group, and when a plurality of substituents are introduced, these substituents may be the same as or different from each other. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (2) to (4).
(2)

(3)

[Chemical Formula 4]

In formulas (2) to (4)
X ₁ to X ₅ , R ₂ to R ₉ And L are as defined in claim 1, respectively. The method according to claim 1,
In the formula 1

Lt; / RTI &gt; is selected from the group of substituents consisting of the following structures.

Wherein R &lt; ₁ &gt; is as defined in claim 1,
(a) is an integer of 0 to 4, provided that when R ₁₀ is plural, R ₁₀ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, an aryloxy group of a heteroaryl group of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to _40, C ₆ ~ C 40 of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ of C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ group consisting arylsilyl of Or may combine with adjacent groups to form a condensed ring. The method according to claim 1,
R ₂ to R ₉ Are each independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group and a substituent represented by the following formula (6).
[Chemical Formula 6]

Y ₁ is selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),
Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl is selected from the group consisting of,
In the above Ar ₁ to Ar ₅ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ The arylphosphine oxide group and the C ₆ to C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl yarn Group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of And arylsilyl group, and when a plurality of substituents are introduced, these substituents may be the same as or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by any one of the following formulas C 1 to C 216.

A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 5. The method according to claim 6,
Wherein at least one of the one or more organic layers including the compound is a phosphorescent light-emitting layer.