KR20150096152A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same. The compound according to the present invention is used in an organic substance layer of an organic electroluminescent device, preferably a light emitting layer, thereby improving such as light emitting efficiency, a driving voltage, and lifespan of the organic electroluminescent device.

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 and an organic electroluminescent device including the same.

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. The material contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.

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

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 dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.

Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known. However, existing materials have advantages in terms of luminescent properties, but their thermal stability is poor due to their low glass transition temperature, which is not satisfactory in terms of lifetime of an organic electroluminescent device.

In order to solve the above problems, it is an object of the present invention to provide a novel organic compound having a high glass transition temperature and excellent thermal stability.

Another object of the present invention is to provide an organic electroluminescent device comprising the organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1) or (2).

In the above formula (1) or (2)

X ₁ and X ₂ are the same or different and are each independently selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) is selected from, wherein X ₁ and X _2, at least one of which is N (Ar ₁₎ a;

L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nucleus atoms,

Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ alkylsulfonyl group, C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxide of a C ₆ ~ C ₄₀ ring And it is selected from the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C _40,

R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted can be a heteroaryl group of from 5 to 40, a substituted or unsubstituted nucleus of atoms of a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, , A substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted A C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to adjacent groups to form a condensed ring,

In the above Ar ₁ to Ar ₅ and R ₁ to R ₄ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic group, 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 at least one member selected from the ₄₀ group consisting of aryl silyl coming And when they are substituted with a plurality of substituents, they may be the same or different,

a and c are each independently an integer of 0 to 4, b is an integer of 0 to 3, and d is an integer of 0 to 6.

The present invention also relates to an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 An electroluminescent device is provided.

Herein, the organic material layer including the compound represented by Formula 1 may be a phosphorescent light emitting layer, a hole transporting layer, or a light emitting auxiliary layer.

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

Hereinafter, the present invention will be described in detail.

<New Organic Compound>

The novel compounds according to the invention can be prepared by reacting a dibenzomo thiophene (dibenzothiophene, dibenzofuran, dibenzosilole, dibenzoselenophene, carbazole or fluorene) with a 5-membered aromatic ring or a 5-membered heteroaromatic ring, (1) or (2) as a basic skeleton.

Carbazole or benzoacridine moiety has a hole mobility of more than a certain level due to its excellent hole transporting ability, the compound represented by the above formula (1) or (2) The performance of the device can be improved when it is applied to an organic material layer (specifically, a hole transport layer) of a light emitting device.

In addition, when an electron-withdrawing group (EWG) having a high electron-absorbing property is bonded to a basic skeleton having a high triplet energy such as the compound represented by the general formula (1) or (2), since the entire molecule has a bipolar characteristic, The bonding strength between holes and electrons in the organic material layer (specifically, the light emitting layer) can be enhanced. Therefore, the light emitting property of the organic EL device can be improved, and the carrier injecting ability, transporting ability, or light emitting efficiency can be improved.

In addition, the compound represented by the above formula (1) or (2) can restrict the migration of the exciton formed in the organic layer to another organic layer (specifically, the migration of the exciton formed in the light emitting layer to the hole transport layer) And efficiency can also be improved.

Furthermore, the compound represented by the above formula (1) or (2) has various substituents, especially an aryl group and / or a heteroaryl group, and the molecular weight of the compound is significantly increased, thereby improving the glass transition temperature. For example, CBP may have higher thermal stability. The compound represented by the above formula (1) or (2) is also effective for inhibiting crystallization of the organic material layer.

Therefore, when the compound represented by the general formula (1) or (2) of the present invention is applied to an organic material layer (specifically, a hole transporting layer, a light emitting auxiliary layer or a light emitting layer) of an organic electroluminescent device, the performance and lifetime characteristics of the organic electroluminescent device have. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

In the compounds represented by formula (1) or (2) of the present invention, L ₁ may be a conventional divalent group linker known in the art. For example, it may be selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nucleus atoms.

Examples of the arylene group and heteroarylene group include, but are not limited to, phenylene, biphenylene, naphthylene, anthracenylene, indenylene, pyranthrenylene, An imidazolylene group, an imidazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like. Specifically, it is preferable that L ₁ is a single bond, a phenylene group, or a biphenylene group.

In the compound represented by the formula (I) or (II) of the present invention, X ₁ and X ₂ are the same or different and are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) And Si (Ar ₄ ) (Ar ₅ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ ). Specifically, it is preferable that X ₁ is N (Ar ₁ ).

Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C of ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted in the ring C ₆ ~ C ₄₀ aryl A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ alkylsulfonyl group, ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxazole of C ₆ ~ C ₄₀ A divalent group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group.

Specifically, each of Ar ₁ to Ar ₅ independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted 5 to 40 And a heteroaryl group, and more preferably a methyl group or a phenyl group.

In the above L ₁ , Ar ₁ to Ar ₅ , and R ₁ to R ₄ , substituents described in the "substituted or unsubstituted" term include alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, An aryloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylsilyl group are respectively substituted by deuterium , A halogen, a cyano group, 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 heterocyclic group having 3 to 40 nuclear atoms alkyl group, C ₁ ~ C ₄₀ alkylsilyl 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 Pin oxide And C ~ ₆ may be substituted with at least one member selected from the group consisting of C ₄₀ aryl silyl. When a plurality of substituents are substituted, they are the same or different from each other.

More specifically, Ar ₁ to Ar ₅ and R ₁ to R ₄ may be selected from the group consisting of hydrogen, or a substituent group consisting of the following substituent groups S1 to S206. However, the present invention is not limited thereto.

In the present invention, at least one of Ar ₁ to Ar ₅ is preferably represented by the following formula (3), and more preferably Ar ₁ is represented by the formula (3), considering the performance of the organic electroluminescent device.

In this case, '*' means a site to be bonded with nitrogen (N).

In Formula 3,

L may be a conventional divalent group linking group known in the art and includes, for example, a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, and a substituted or unsubstituted 5 to 18 &Lt; / RTI &gt; heteroarylene groups of the formula &lt; RTI ID = 0.0 &gt;

More specific examples of the L include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, An imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group and the like. In Formula 3, L is preferably a single bond, a phenylene group or a biphenylene group.

Y ₁ to Y ₅ are each independently N or C (R ₁₁ ), and at least one of Y ₁ to Y ₅ is preferably N.

R ₁₁ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl, substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, An unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C _An arylsilyl group having ₆ to ₄₀ carbon atoms, or an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring.

Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the 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 alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _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 ~ C ₄₀ aryl phosphine group may be substituted with at least one member selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the. Wherein when substituted with a plurality of substituents, they may be the same or different.

The substituent represented by the above-mentioned formula (3) may be further specified by any one of substituent groups composed of the structures (substituents) shown by the following A-1 to A-15.

In the above A-1 to A-15,

L and R &lt; ₁₁ &gt; are the same as defined in the above formula (3)

When a plurality of C (R ₁₁ ) s are present, a plurality of R _{11 s} may be the same or different from each other,

R ₁₂ represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, An unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C _And an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring, and n is an integer of 1 to 4.

Alkyl group of the R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the 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 alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _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 ~ C ₄₀ aryl phosphine group may be substituted with at least one member selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the. Wherein when substituted with a plurality of substituents, they may be the same or different.

Specifically, the above-mentioned formula (3) can be selected from the group of substituents composed of the following structures (substituents).

The compound represented by the formula (1) or (2) of the present invention may be further compounded by any one of the compounds represented by the following formulas (4) to (6).

In the above Chemical Formulas 4 to 6,

X ₁ and X ₂ , R ₁ to R _{4, and} a to d are the same as defined in the above formula (1).

According to a preferred embodiment of the present invention, X ₁ and X ₂ are the same or different and are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄ ) (Ar ₅ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ )

Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted 5 to 40 &Lt; / RTI &gt; heteroaryl groups of &lt; RTI ID = 0.0 &gt;

R ₁ to R ₄ are the same or different and each independently represents hydrogen, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted A heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

The compound represented by the formula (1) of the present invention described above can be further exemplified by the following exemplified compounds, for example, compounds represented by C-1 to C-300. However, the compounds represented by formula (1) of the present invention are not limited to the following compounds.

"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.

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

"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.

In the present invention, "aryl" 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. 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 6 to 60 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 have a linear, branched or cyclic structure . 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.

"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 is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compound represented by the formula (1) or (2) of the present invention can be synthesized according to a general synthesis method. These compounds of the present invention can be synthesized in various ways with reference to the following Synthesis Examples.

&Lt; Organic electroluminescent device &

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) or (2) according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Includes a compound represented by the above formula (1) or (2). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer. can do. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 or 2 is a light emitting layer, a hole transporting layer, or a light emitting auxiliary layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 or 2 as a host material. Thus, when the compound of Formula 1 or 2 is contained as a light emitting layer material of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, or red, bonding power between holes and electrons in the light emitting layer is increased, It is possible to improve the efficiency (luminous efficiency and power efficiency), lifetime, luminance and driving voltage of the device. Meanwhile, when the compound represented by the general formula (1) or (2) of the present invention is used as a luminescent auxiliary layer, it may be located between the hole transporting layer and the light emitting layer. At this time, the compound may be a phosphorescent light-emitting auxiliary layer. In this case, the luminous efficiency, luminance, power efficiency, thermal stability and lifetime of the device can be improved due to the compound.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary 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 auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably includes a hole transporting layer, May include a compound represented by the above formula (1). Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. On the other hand, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention may be formed by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer (preferably a light emitting layer) of the organic material layer contains the compound represented by the above formula Can be manufactured.

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 used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and 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 ordinary 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 1] Synthesis of IC1-1

<Step 1> Synthesis of 8- (3-chlorophenyl) naphthalen-1-amine

(13.3 g, 60.0 mmol), 3-chlorophenylboronic acid (10.3 g, 66.0 mmol), NaOH (7.20 g, 180.0 mmol) and THF / H ₂ O (80 ml / 40 ml ), Pd (PPh ₃ ) ₄ (3.48 g, 5 mol%) was added thereto, 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 added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 8- (3-chlorophenyl) naphthalen-1-amine (13.2 g, yield 87%).

^{1 H-NMR: δ 5.74 (} s, 2H), 6.68 (d, 1H), 7.12 (t, 1H), 7.52 (m, 4H), 7.77 (m, 2H), 7.95 (d, 1H), 8.40 ( d, 1 H)

<Step 2> Synthesis of 1-azido-8- (3-chlorophenyl) naphthalene

150 ml of 5% HCl was added to 8- (3-chlorophenyl) naphthalen-1-amine (11.4 g, 45.0 mmol), stirred for 30 minutes, NaNO ₂ (3.73 g, 54.0 mmol) was dissolved in 30 ml of water and slowly added thereto, followed by stirring for 30 minutes. And at 0 ° C NaN ₃ (3.51 g, 54.0 mmol) was dissolved in 30 ml of water and slowly added thereto. The mixture was stirred at room temperature for 1 hour and neutralized with NaHCO ₃ .

The mixture was extracted with methylene chloride, dried over MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 1-azido-8- (3-chlorophenyl) naphthalene (8.69 g, yield 69%).

^{1 H-NMR: δ 7.43 (} m, 2H), 7.53 (m, 2H), 7.71 (m, 3H), 8.00 (m, 2H), 8.41 (d, 1H)

<Step 3> Synthesis of 10-chloro-7H-benzo [kl] acridine

1-azido-8- (3-chlorophenyl) naphthalene (8.39 g, 30.0 mmol) was dissolved in 100 ml of 1,2-dichlorobenzene, And stirred for 2 hours. After removing the organic layer solvent, the residue was purified by column chromatography to obtain 10-chloro-7H-benzo [kl] acridine (3.93 g, yield 52%).

^{1 H-NMR: δ 6.43 (} d, 1H), 6.84 (m, 2H), 6.89 (d, 1H), 7.13 (d, 1H), 7.25 (m, 2H), 7.47 (d, 1H), 7.75 ( d, 1 H), 9.79 (s, 1 H)

Step 4 Synthesis of 10-chloro-7-phenyl-7H-benzo [kl] acridine

Iodobenzene (14.1 g, 69.0 mmol), Cu powder (0.15 g, 2.30 mmol) and K ₂ CO ₃ (6.30 g, 46.0 mmol) were added to a solution of 10-chloro-7H- mmol), Na ₂ SO ₄ (6.50 g, 46.0 mmol) and nitrobenzene (150 ml) were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography to obtain 5.58 g (yield 74%) of 10-chloro-7-phenyl-7H-benzo [kl] acridine.

^{1 H-NMR: δ 6.68 (} m, 3H), 6.94 (m, 2H), 7.22 (m, 4H), 7.59 (m, 2H), 7.78 (d, 1H), 8.00 (d, 1H), 8.41 ( d, 1 H)

<Step 5> Synthesis of IC1-1

Carbazol-3-ylboronic acid (4.22 g, 20.0 mmol) and NaOH (1.80 g, 45.0 mmol) were added to a solution of 10-chloro-7-phenyl-7H- and it was stirred for 12 hours in a mixture of _{THF / H 2 O (80 ml} / 40 ml) , and _{then, Pd (PPh 3) 4 80} ℃ into the (0.87 g, 5 mol%) .

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain IC1-1 (6.33 g, yield 92%).

^{1 H-NMR: δ 6.64 (} m, 3H), 6.98 (m, 2H), 7.22 (m, 3H), 7.42 (m, 2H), 7.52 (m, 4H), 7.65 (m, 2H), 7.79 ( (d, IH), 8.40 (d, IH), 10.02 (s, IH)

[Preparation Example 2] Synthesis of IC1-2

<Step 1> Synthesis of N- (8-bromonaphthalen-1-yl) acetamide

8-bromonaphthalen-1-amine (13.3 g, 60.0 mmol) and acetic anhydride (5.6 ml, 60.0 mmol) were added to 50 ml of pyridine and stirred at 100 ° C for 1 hour. After concentrating the organic layer, 200 ml of HCl was added and the solid was filtered. The residue was dissolved in 40 ml of AcOH and recrystallized from 40 ml of H ₂ O to obtain N- (8-bromonaphthalen-1-yl) acetamide (13.5 g, yield 85%).

^{1 H-NMR: δ 2.06 (} s, 3H), 7.34 (m, 2H), 7.52 (t, 1H), 7.81 (d, 1H), 7.90 (d, 1H), 7.96 (d, 1H), 9.82 ( s, 1 H)

<Step 2> Synthesis of N- (8- (5-chloro-2-methoxyphenyl) naphthalen-1-yl) acetamide

(7.92 g, 30.0 mmol), 5-chloro-2-methoxyphenylboronic acid (6.15 g, 33.0 mmol) and Na ₂ CO ₃ (9.54 g, 90.0 mmol) and stirred for 2 hours in a mixture of _{DME / H 2 O (120 ml} / 60 ml) , and _{then, Pd (PPh 3) 4 (} 1.74 g, 5 mol%) 80 ℃ put.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography to give N- (8- (5-chloro-2-methoxyphenyl) naphthalen-1-yl) acetamide (8.50 g, yield 87%).

^{1 H-NMR: δ 1.37 (} s, 3H), 3.59 (s, 3H), 7.04 (d, 1H), 7.22 (m, 3H), 7.33 (d, 1H), 7.55 (m, 2H), 7.94 ( d, 1 H), 8.01 (d, 1 H), 8.85 (s, 1 H)

<Step 3> Synthesis of 10-chlorobenzo [kl] xanthene

1-yl) acetamide (8.14 g, 25.0 mmol) was added to 100 ml of HBr and 60 ml of AcOH, and the mixture was stirred at 100 ° C for 6 hours. After neutralization with NaHCO ₃ , extraction with methylene chloride, adding MgSO ₄ , and filtration. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 10-chlorobenzo [kl] xanthene (4.11 g, yield 65%).

¹ H-NMR:? 7.06 (d, IH), 7.25 (d, IH), 7.47 (m, 3H), 7.56 (t, s, 1 H)

<Step 4> Synthesis of IC2-2

Carbazol-3-ylboronic acid (4.22 g, 20.0 mmol), NaOH (1.80 g, 45.0 mmol) and THF / H ₂ O (80 mL) a mixture of ml / 40 ml) into the _{following, Pd (PPh 3) 4 (} 0.87 g, 5 mol%) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain IC1-2 (5.06 g, yield 88%).

^{1 H-NMR: δ 6.99 (} d, 1H), 7.15 (t, 1H), 7.25 (d, 1H), 7.45 (m, 6H), 7.72 (m, 3H), 8.08 (d, 1H), 8.22 ( (d, IH), 8.38 (s, IH), 8.56 (s, IH), 11.29

[Preparation Example 3] Synthesis of IC1-3

<Step 1> Synthesis of N- (8- (5-chloro-2- (methylthio) phenyl) naphthalen-1-yl) acetamide

(7.92 g, 30.0 mmol), 5-chloro-2- (methylthio) phenylboronic acid (6.68 g, 33.0 mmol) and Na ₂ CO ₃ (9.54 g, 90.0 mmol) and a mixture of _{DME / H 2 O (120 ml} / 60 ml) , and then, Pd (PPh ₃₎ into a _{4 (1.74 g, 5 mol%} ) was stirred for 2 h at 80 ℃.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain N- (8- (5-chloro-2- (methylthio) phenyl) naphthalen-1-yl) acetamide (8.30 g, yield 81%).

^{1 H-NMR: δ 1.43 (} s, 3H), 3.72 (s, 3H), 7.08 (d, 1H), 7.25 (m, 3H), 7.33 (d, 1H), 7.57 (m, 2H), 7.94 ( d, 1 H), 8.02 (d, 1 H), 8.89 (s, 1 H)

<Step 2> Synthesis of 10-chlorobenzo [kl] thioxanthene

1-yl) acetamide (8.55 g, 25.0 mmol) was added to 100 ml of HBr and 60 ml of AcOH, and the mixture was stirred at 100 ° C for 6 hours. After neutralization with NaHCO ₃ , extraction with methylene chloride, adding MgSO ₄ , and filtration. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 10-chlorobenzo [kl] thioxanthene (4.57 g, yield 68%).

^{1 H-NMR: δ 7.11 (} d, 1H), 7.29 (d, 1H), 7.49 (m, 3H), 7.56 (t, 1H), 7.82 (d, 1H), 7.99 (d, 1H), 8.24 ( s, 1 H)

<Step 3> Synthesis of IC2-3

3-ylboronic acid (4.22 g, 20.0 mmol), NaOH (1.80 g, 45.0 mmol) and THF / H ₂ O (80 mL) were added to a solution of 10-chlorobenzo [kl] thioxanthene a mixture of ml / 40 ml) into the _{following, Pd (PPh 3) 4 (} 0.87 g, 5 mol%) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain IC1-3 (4.85 g, yield 81%).

^{1 H-NMR: δ 6.95 (} d, 1H), 7.22 (m, 2H), 7.46 (m, 6H), 7.77 (m, 3H), 8.08 (d, 1H), 8.20 (d, 1H), 8.39 ( s, 1 H), 8.53 (s, 1 H), 11.22 (s, 1 H)

[Synthesis Example 1] Synthesis of C-1

Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol), (t-Bu) ₃ P (0.40 g, 2.0 mmol), sodium iodide (1.58 g, 10.00 mmol) tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and the mixture was stirred at 110 ° 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, the desired compound C-1 (4.32 g, yield 81%) was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 534

[Synthesis Example 2] Synthesis of C-7

(5.14 g, yield 75%) was obtained by carrying out the same processes as in Synthesis Example 1, except that 1-bromo-3,5-diphenylbenzene (3.08 g, 10.00 mmol) .

MS [M + 1] &lt; ⁺ &gt; 686

[Synthesis Example 3] Synthesis of C-9

The target compound C-9 (5.39 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 2- (4-bromophenyl) triphenylene (3.82 g, 10.00 mmol) was used in place of bromobenzene .

MS [M + 1] &lt; ⁺ &gt; 760

[Synthesis Example 4] Synthesis of C-11

(5.01 g, yield 79%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 3'-bromobiphenyl-3-carbonitrile (2.56 g, 10.00 mmol) was used instead of bromobenzene .

MS [M + 1] &lt; ⁺ &gt; 635

[Synthesis Example 5] Synthesis of C-12

(4.86 g, 10.00 mmol) was obtained by following the same procedure as Synthesis Example 1, except that 4- (4-bromophenyl) dibenzo [b, d] thiophene Yield: 68%).

MS [M + 1] &lt; ⁺ &gt; 716

[Synthesis Example 6] Synthesis of C-16

(5.46 g, yield 78%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 4-bromo-N, N-diphenylaniline (3.23 g, 10.00 mmol) .

MS [M + 1] &lt; ⁺ &gt; 701

[Synthesis Example 7] Synthesis of C-19

The procedure of Synthesis Example 1 was repeated except that 3-chloro-4,5-diphenyl-4H-1,2,4-triazole (2.55 g, 10.00 mmol) 19 (5.41 g, yield 80%).

MS [M + 1] &lt; ⁺ &gt; 677

[Synthesis Example 8] Synthesis of C-30

(5.24 g, yield 75%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromo-9-phenyl-9H-carbazole (3.21 g, 10.00 mmol) ).

MS [M + 1] &lt; ⁺ &gt; 699

[Synthesis Example 9] Synthesis of C-62

(5.50 g, yield 80%) was obtained by carrying out the same processes as in Synthesis Example 1, except that 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) .

MS [M + 1] &lt; ⁺ &gt; 688

[Synthesis Example 10] Synthesis of C-63

(5.16 g, yield 75%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) .

MS [M + 1] &lt; ⁺ &gt; 688

[Synthesis Example 11] Synthesis of C-65

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) was used instead of bromobenzene to obtain the desired compound C-65 4.82 g, yield 70%).

MS [M + 1] &lt; ⁺ &gt; 689

[Synthesis Example 12] Synthesis of C-68

68 (4.96 g, yield: 97%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 2- (4-chlorophenyl) -4,6-diphenylpyrimidine (3.42 g, 10.00 mmol) 65%).

MS [M + 1] &lt; ⁺ &gt; 764

[Synthesis Example 13] Synthesis of C-69

The objective Compound C-69 (4.58 g, yield) was obtained in the same manner as in Synthesis Example 1, except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (3.42 g, 10.00 mmol) 60%).

MS [M + 1] &lt; ⁺ &gt; 764

[Synthesis Example 14] Synthesis of C-73

The objective Compound C-73 (4.96 g, yield: 97%) was obtained in the same manner as in Synthesis Example 1, except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (3.42 g, 10.00 mmol) 65%).

MS [M + 1] &lt; + &gt; 764

[Synthesis Example 15] Synthesis of C-74

The objective Compound C-74 (6.11 g, yield: 82%) was obtained in the same manner as in Synthesis Example 1, except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.42 g, 10.00 mmol) 80%).

MS [M + 1] &lt; ⁺ &gt; 764

[Synthesis Example 16] Synthesis of C-75

The procedure of Synthesis Example 1 was repeated except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol) C-75 (5.35 g, yield 70%).

MS [M + 1] &lt; ⁺ &gt; 765

[Synthesis Example 17] Synthesis of C-101

(3.44 g, yield 75%) was obtained in the same manner as in Synthesis Example 1, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 459

[Synthesis Example 18] Synthesis of C-107

The objective Compound C-107 (4.09 g, yield 67%) was obtained in the same manner as in Synthesis Example 2, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 611

[Synthesis Example 19] Synthesis of C-109

The objective Compound C-109 (4.72 g, yield 69%) was obtained in the same manner as in Synthesis Example 3, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 685

[Synthesis Example 20] Synthesis of C-111

The target compound C-111 (4.25 g, yield 76%) was obtained in the same manner as in Synthesis Example 4, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 560

[Synthesis Example 21] Synthesis of C-112

The objective compound C-112 (4.55 g, yield 71%) was obtained in the same manner as in Synthesis Example 5, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 641

[Synthesis Example 22] Synthesis of C-116

The objective Compound C-116 (4.25 g, yield 68%) was obtained in the same manner as in Synthesis Example 6, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 626

[Synthesis Example 23] Synthesis of C-119

The target compound C-119 (4.21 g, yield 70%) was obtained in the same manner as in Synthesis Example 7, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 24] Synthesis of C-130

The objective compound C-130 (4.62 g, yield 74%) was obtained in the same manner as in Synthesis Example 8, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 624

[Synthesis Example 25] Synthesis of C-162

The objective compound C-162 (4.53 g, yield 73%) was obtained in the same manner as in Synthesis Example 9, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 613

[Synthesis Example 26] Synthesis of C-163

The target compound C-163 (4.29 g, yield 70%) was obtained by following the same procedure as in Synthesis Example 10, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 613

[Synthesis Example 27] Synthesis of C-165

The objective compound C-165 (4.11 g, yield 67%) was obtained in the same manner as in Synthesis Example 11, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 614

[Synthesis Example 28] Synthesis of C-168

The objective Compound C-168 (4.89 g, yield 71%) was obtained in the same manner as in Synthesis Example 12, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 689

[Synthesis Example 29] Synthesis of C-169

The target compound C-169 (4.75 g, yield 69%) was obtained in the same manner as in Synthesis Example 13, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 689

[Synthesis Example 30] Synthesis of C-173

The target compound C-173 (5.02 g, yield 73%) was obtained in the same manner as in Synthesis Example 14, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 689

[Synthesis Example 31] Synthesis of C-174

The target compound C-174 (4.82 g, yield 70%) was obtained in the same manner as in Synthesis Example 15, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 689

[Synthesis Example 32] Synthesis of C-175

The objective Compound C-175 (4.96 g, yield 72%) was obtained in the same manner as in Synthesis Example 16, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 690

[Synthesis Example 33] Synthesis of C-201

The objective compound C-201 (3.46 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 475

[Synthesis Example 34] Synthesis of C-207

The target compound C-207 (4.38 g, yield 70%) was obtained in the same manner as in Synthesis Example 2, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 627

[ Synthetic example  35] Synthesis of C-209

The target compound C-209 (5.32 g, yield 76%) was obtained in the same manner as in Synthesis Example 3, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 701

[Synthesis Example 36] Synthesis of C-211

The objective compound C-211 (4.14 g, yield 72%) was obtained in the same manner as in Synthesis Example 4, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 576

[Synthesis Example 37] Synthesis of C-212

The objective compound C-212 (4.92 g, yield 75%) was obtained in the same manner as in Synthesis Example 5, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 657

[Synthesis Example 38] Synthesis of C-216

The objective compound C-216 (4.42 g, yield 69%) was obtained in the same manner as in Synthesis Example 6, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 642

[Synthesis Example 39] Synthesis of C-219

The objective compound C-219 (4.38 g, yield 71%) was obtained in the same manner as in Synthesis Example 7, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 618

[Synthesis Example 40] Synthesis of C-230

The objective compound C-230 (4.73 g, yield 74%) was obtained in the same manner as in Synthesis Example 8, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 640

[Synthesis Example 41] Synthesis of C-262

The target compound C-262 (4.40 g, yield 70%) was obtained in the same manner as in Synthesis Example 9, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 629

[Synthesis Example 42] Synthesis of C-263

The objective compound C-263 (4.08 g, yield 65%) was obtained in the same manner as in Synthesis Example 10, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 629

[Synthesis Example 43] Synthesis of C-265

The target compound C-265 (4.53 g, yield 72%) was obtained in the same manner as in Synthesis Example 11, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 630

[ Synthetic example  44] Synthesis of C-268

The target compound C-268 (5.00 g, yield 71%) was obtained in the same manner as in Synthesis Example 12, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 705

[Synthesis Example 45] Synthesis of C-269

The objective compound C-269 (4.86 g, yield 69%) was obtained in the same manner as in Synthesis Example 13, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 705

[Synthesis Example 46] Synthesis of C-273

The target compound C-273 (5.14 g, yield 73%) was obtained in the same manner as in Synthesis Example 14, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 705

[Synthesis Example 47] Synthesis of C-274

The objective compound C-274 (4.93 g, yield 70%) was obtained in the same manner as in Synthesis Example 15, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 705

[Synthesis Example 48] Synthesis of C-275

The objective Compound C-275 (5.22 g, yield 74%) was obtained in the same manner as in Synthesis Example 16, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.

MS [M + 1] &lt; ⁺ &gt; 706

[Examples 1 to 48] Fabrication of green organic EL device

The compounds synthesized in Synthesis Examples 1 to 48 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) 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.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / C-1 to C-26 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in that order.

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

[Comparative Example 1] Production of green organic EL device

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-1 as a luminescent host material in forming the light emitting layer.

[Evaluation example]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 48 and Comparative Example 1, and the results are shown in Table 1 below .

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 C-1 6.70 517 41.2 Example 2 C-7 6.66 518 40.7 Example 3 C-9 6.55 517 39.9 Example 4 C-11 6.70 516 40.1 Example 5 C-12 6.60 518 39.6 Example 6 C-16 6.68 518 39.3 Example 7 C-19 6.65 517 40.7 Example 8 C-30 6.68 518 39.9 Example 9 C-62 6.65 517 41.1 Example 10 C-63 6.50 517 41.1 Example 11 C-65 6.55 518 41.4 Example 12 C-68 6.50 518 41.5 Example 13 C-69 6.60 516 41.9 Example 14 C-73 6.55 518 41.3 Example 15 C-74 6.45 517 42.1 Example 16 C-75 6.60 518 42.3 Example 17 C-101 6.71 518 39.1 Example 18 C-107 6.67 517 39.1 Example 19 C-109 6.58 516 38.9 Example 20 C-111 6.76 518 40.1 Example 21 C-112 6.72 517 40.0 Example 22 C-116 6.71 517 41.0 Example 23 C-119 6.72 518 38.9 Example 24 C-130 6.76 517 39.1 Example 25 C-162 6.60 518 41.3 Example 26 C-163 6.50 517 41.0 Example 27 C-165 6.55 517 41.5 Example 28 C-168 6.50 516 41.8 Example 29 C-169 6.55 518 41.9 Example 30 C-173 6.55 517 41.3 Example 31 C-174 6.50 517 42.1 Example 32 C-175 6.45 518 42.3 Example 33 C-201 6.70 517 39.1 Example 34 C-207 6.67 518 39.1 Example 35 C-209 6.65 517 38.9 Example 36 C-211 6.70 518 40.1 Example 37 C-212 6.70 517 40.0 Example 38 C-216 6.71 517 41.0 Example 39 C-219 6.72 517 38.9 Example 40 C-230 6.75 516 39.1 Example 41 C-262 6.65 518 42.0 Example 42 C-263 6.50 517 41.9 Example 43 C-265 6.55 517 41.4 Example 44 C-268 6.50 518 41.5 Example 45 C-269 6.45 517 41.9 Example 46 C-273 6.50 518 41.8 Example 47 C-274 6.45 517 42.2 Example 48 C-275 6.50 517 42.1 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL device of Example 1-48, in which the compound according to the present invention was used as a light emitting layer of a green organic EL device, compared with the green organic EL device of Comparative Example 1 using conventional CBP It was found that the device exhibited better performance in terms of efficiency and driving voltage.

Claims (7)

A compound represented by the following formula (1) or (2):
[Chemical Formula 1]

(2)

In the above formula (1) or (2)
X ₁ and X ₂ are the same or different and are each independently selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) is selected from, wherein X ₁ and X _2, at least one of which is N (Ar ₁₎ a;
L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nucleus atoms,
Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ alkylsulfonyl group, C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxide of a C ₆ ~ C ₄₀ ring And it is selected from the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C _40,
R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted can be a heteroaryl group of from 5 to 40, a substituted or unsubstituted nucleus of atoms of a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, , A substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted A C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to adjacent groups to form a condensed ring,
In the above Ar ₁ to Ar ₅ and R ₁ to R ₄ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic group, 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 at least one member selected from the ₄₀ group consisting of aryl silyl coming And when they are substituted with a plurality of substituents, they may be the same or different,
a and c are each independently an integer of 0 to 4, b is an integer of 0 to 3, and d is an integer of 0 to 6. The compound according to claim 1, wherein Ar ₁ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, A substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms. The compound according to claim 1, wherein at least one of Ar ₁ to Ar ₅ is represented by the following formula (3).
(3)

In Formula 3,
L is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,
Y ₁ to Y ₅ are the same or different and are each independently N or C (R ₁₁ ), wherein at least one of Y ₁ to Y ₅ is N,
R ₁₁ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl, substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, An unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C _An arylsilyl group having ₆ to ₄₀ carbon atoms, or an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring,
Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the 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 alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _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 ~ C ₄₀ aryl phosphine group may be substituted with at least one member selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the. 4. The compound according to claim 3, wherein the formula (3) is selected from the group consisting of the substituents represented by the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,
L ₁ and R ₁₁ are as defined in claim 3, wherein a plurality of R _{11 s} are the same as or different from each other,
R ₁₂ represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, An unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom number A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C Or an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring,
Alkyl group of the R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the 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 alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _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 ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl, and silyl may be substituted by one or more selected from the group consisting of a,
n is an integer of 1 to 4; The compound according to claim 1, wherein the formula (1) or (2) is represented by any one of the following formulas (4) to (6).
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Chemical Formulas 4 to 6,
X ₁ and X ₂ , R ₁ to R _{4 , and} a to d are the same as defined in claim 1, respectively. 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 organic electroluminescent device according to claim 6, wherein the organic compound layer containing the compound is a light emitting layer, a hole transporting layer, or a light emitting auxiliary layer.