KR20150086069A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to novel organic compounds and an organic electroluminescent device comprising the same. The organic electroluminescent device has improved properties such as light emitting efficiency, driving voltage, lifespan, etc. by introducing a light emitting layer which uses the compounds of the present invention as a host material to the organic electroluminescent device. The organic compounds are 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.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observations of organic thin film emission 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. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, researches 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. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

However, existing materials have an advantage in terms of luminescence properties, but their thermal stability is not very good 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 is selected from the group consisting of N (Ar ₂ ), O, S, C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );

Y ₁ is a non-bond, or a single bond;

Ar ₁ to Ar ₆ 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 ₁₂ are the same or different and each independently 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 alkene 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 C _An arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and a substituted or unsubstituted arylsilyl group having ₆ to ₄₀ carbon atoms, or they may be bonded to adjacent groups to form a condensed ring,

In the Ar ₁ to Ar ₆ and R ₁ to R ₁₂ , 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 nucleus A heteroaryl group having 5 to 40 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 nucleus A heterocyclic alkyl group having 3 to 40 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 group, C ₆ to C ₄₀ arylphosphine oxide groups and C ₆ to C ₄₀ arylsilyl groups 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 ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, having 3 to 40 nuclear atoms of the heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₄₀ group, and A C ₆ to C ₄₀ arylsilyl group, and the like. At this time, when there are a plurality of substituents, the plurality of substituents may independently be mutually the same or different.

Also, the present invention is an organic electroluminescent device comprising a cathode, 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 of the above formula And an organic electroluminescent device.

At least one of the one or more organic layers 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, and is preferably a light emitting layer. At this time, the compound represented by Formula 1 is a blue, green or red phosphorescent host material.

The compound represented by the general 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 produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time as compared with conventional host materials, And a full color display panel in which the lifetime is greatly improved can also be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The compound represented by the formula (1) of the present invention is a compound in which dibenzo moiety including fluorene or a 5-membered heterocycle (furan, thiophene, and silole) is bonded to a carbazole to form an octane ring .

Energy transfer from the host to the dopant is important in order to obtain high-efficiency phosphorescence. At this time, the host must have a larger triplet energy than the dopant, so that the energy transferred to the dopant can be prevented from being reversed to the host, resulting in high luminescence efficiency. The compound of the present invention in which a carbazole having a high triple energy and a dibenzomoate containing a fluorene or a 5-membered heterocycle (furan, thiophene, and silole) are fused to form a ring, It is easy to transfer carriers to the dopant while keeping energy, and it is also easy to confine the energy.

In addition, the compound represented by the formula (1) of the present invention may have a bipolar compound as a whole depending on the characteristics of the substituent to be bonded. When a substituent is an electron withdrawing group (EWG) having a high electron absorbing property, it has a bipolar, thereby not only having a wide band gap but also enhancing the bonding force between holes and electrons. Therefore, it is possible to improve the phosphorescence characteristic of the organic EL device and improve the hole injecting ability, transporting ability, or light emitting efficiency.

In addition, since the aromatic ring substituent significantly increases the molecular weight of the compound, the glass transition temperature can be improved, and thus it can have higher thermal stability than conventional 4,4-dicarbazolylbiphenyl (CBP) . Therefore, the organic EL device including the compound of the formula (1) according to the present invention can also significantly improve the durability and lifetime characteristics, effectively suppressing the crystallization of the organic material layer.

Specifically, when the compound represented by the formula (1) of the present invention is used as a blue, green and / or red phosphorescent host material as a material for a positive hole injection / transport layer of an organic EL device, the efficiency and life Excellent effect can be exhibited. Therefore, the compound represented by the general formula (1) of the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device, and the lifetime of the organic EL device can be maximized in the full color organic light emitting panel.

In the compound represented by Formula 1 of the present invention, X ₁ is selected from the group consisting of N (Ar ₂ ), O, S, C (Ar ₃ ) (Ar ₄ ), and Si (Ar ₅ ) (Ar ₆ ). When the _{double-N (Ar 2), O,} S one time and preferably, N (Ar ₂₎ is most preferred.

Ar ₁ to Ar ₆ 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, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or And an unsubstituted C ₆ to C ₄₀ arylsilyl group.

In consideration of the characteristics of the organic EL device in the present invention, Ar ₁ to Ar ₆ each independently represent a substituted or unsubstituted C ₆ to C ₄₀ aryl group, or a substituted or unsubstituted heteroaromatic group having 5 to 40 nucleus atoms It is preferably an aryl group. More preferably, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₄₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms.

R ₁ to R ₁₂ are the same or different and each independently 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 alkene 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 C _An arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and a substituted or unsubstituted arylsilyl group having ₆ to ₄₀ carbon atoms, or they may be bonded to adjacent groups to form a condensed ring.

In the present invention, R ₁ to R ₁₂ 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 a heteroaryl group having 5 to 40 unsubstituted nuclear atoms.

In the above Ar ₁ to Ar ₆ and R ₁ to R ₁₂ , a moiety having the above-mentioned term "substituted or unsubstituted", that is, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _40, 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 ~ aryl of C ₄₀ boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ aryl silyl group of each independently a heavy hydrogen, a halogen, cyano group, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the An aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C _{4 0} cycloalkyl, 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, and may be substituted with at least one element C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of aryl silyl group of C _40. Here, when a plurality of substituents are present, a plurality of substituents may be the same or different.

The compound represented by the formula (1) of the present invention can be further specified by the following formula (2) or (3). The compound represented by the formula (2) or (3) is preferable in consideration of the characteristics of the organic EL device.

In the general formulas (2) and (3)

X ₁ , Ar ₁ and R ₁ to R ₁₂ are the same as defined in the above-mentioned formula (1).

G. A preferred embodiment of the present invention, X ₁ is _{N (Ar 2), O,} S, C (Ar 3) (Ar 4) and Si (Ar ₅₎ is selected from _{(Ar 6), N (Ar} 2), O, it is most preferred when the preferred and when S, N (Ar _2).

Ar ₁ to Ar ₆ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, This is preferable in consideration of the characteristics of the EL element. More preferably, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₄₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms.

R ₁ to R ₁₂ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl , 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 , C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C _40, and may be selected from the group consisting arylsilyl of, or coupled to a condensed ring group to which it is adjacent . Preferably, R ₁ to R ₁₂ each independently represent 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 5 to 5 nucleus atoms To about 40 heteroaryl groups.

In the compound of formula (I) according to the present invention, Ar ₁ to Ar ₆ and R ₁ to R ₁₂ are each independently preferably hydrogen or a substituent group selected from the following S1 to S204, but are not limited thereto.

The compounds of the present invention described above can be further exemplified by the following exemplified structures. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

In the present invention, "alkyl" 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, , Hexyl, and the like.

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 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.

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 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, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2- isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include 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 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 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 heterocycloalkyl include 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.

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 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.

&Lt; Organic electroluminescent device &

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, A compound represented by the formula (1), preferably a compound represented by the formula (2) or (3). At this time, the compound of formula (1) 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. [ At this time, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer.

Specifically, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, wherein the host material may include the compound of Formula 1 above. 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 represented by the general formula (1) of the present invention can be used as a phosphorescent host material in the light emitting layer. On the other hand, 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 of the organic material layers (for example, the light emitting layer) An organic material layer and an electrode.

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 1] Synthesis of Compound IC-1

Synthesis of 4,5-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole

(41.6 g, 0.128 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1 , 3,2-dioxaborolane) (71.35 g , 0.281 mol), and mixing _{Pd (dppf) Cl 2 (5.2} g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) And the mixture was stirred at 130 DEG C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v) 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (13.41 g, yield 25%).

¹ H-NMR:? 1.25 (s, 24H), 7.40 (m, 4H), 7.63

<Step 2> IC- Synthesis of 1

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (31.60 g, prepared in Step 1 of Preparation Example 1) (30.84 g, 75.41 mmol), K ₂ CO ₃ (20.84 g, 150.82 mmol) and THF / H ₂ O (400 ml / 200 ml ) a mixture, and then insert the _{Pd (PPh 3) 4 (4.36} g, 5 mol%) at 40 ℃ was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain Compound IC-1 (6.77 g, yield: 22%).

^{1 H-NMR: δ 6.61 (} m, 4H), 6.88 (m, 5H), 7.21 (t, 2H), 7.43 (m, 4H), 7.59 (d, 2H), 7.77 (d, 2H), 11.20 ( s, 1 H)

[Preparation Example 2] Synthesis of compound IC-2

<Step 1> Synthesis of IC-2

Bis (3-bromophenyl) amine (24.66 g, 75.41 mmol) was used instead of 3-bromo-N- (3-bromophenyl) -N-phenylaniline used in Step 2 of Preparation Example 1 Compound IC-2 was obtained by following the procedure of <Step 2> of Preparation Example 1, except that the compound IC-2 was used.

^{1 H-NMR: δ 4.74 (} s, 1H), 6.69 (m, 4H), 7.44 (m, 4H), 7.58 (m, 4H), 7.80 (d, 2H), 10.92 (s, 1H)

[Preparation Example 3] Synthesis of Compound IC-3

<Step 1> Synthesis of IC-3

9-phenyl-9H-carbazole (30.24 g, 75.41 mmol) instead of the 3-bromo-N- (3-bromophenyl) -N-phenylaniline used in <Step 2> Compound IC-3 was obtained by following the procedure of <Step 2> of Preparation Example 1, except that the compound IC-3 was used.

¹ H-NMR:? 7.37 (m, 5H), 7.59 (m, 10H), 7.90

[Preparation Example 4] Synthesis of Compound IC-4

<Step 1> Synthesis of IC-4

4,5-dibromo-9H-carbazole (24.50 g, 75.41 mmol) was used instead of 3-bromo-N- (3-bromophenyl) -N-phenylaniline used in <Step 2> Compound IC-4 was obtained in the same manner as in < Step 2 >

^{1 H-NMR: δ 7.37 (} t, 4H), 7.62 (m, 8H), 10.12 (s, 2H)

[Preparation Example 5] Synthesis of Compound IC-5

<Step 1> Synthesis of IC-5

Dibromodibenzo [b, d] thiophene (25.79 g, 75.41 mmol) instead of the 3-bromo-N- (3-bromophenyl) -N-phenylaniline used in Step 2 of Preparation Example 1 Compound IC-5 was obtained in the same manner as in < Step 2 >

^{1 H-NMR: δ 7.38 (} t, 2H), 7.57 (m, 8H), 7.98 (d, 2H), 10.57 (s, 1H)

[Preparation Example 6] Synthesis of compound IC-6

<Step 1> Synthesis of IC-6

Dibromodibenzo [b, d] furan (24.58 g, 75.41 mmol) was used instead of 3-bromo-N- (3-bromophenyl) -N-phenylaniline used in Step 2 of Preparation Example 1 Compound IC-6 was obtained in the same manner as in < Step 2 >

^{1 H-NMR: δ 7.38 (} m, 4H), 7.63 (m, 8H), 10.30 (s, 1H)

[Synthesis Example 1] Synthesis of Compound C-1

(18.86 g, 46.17 mmol), 2- (4-bromophenyl) triphenylene (21.23 g, 55.40 mmol), Cu powder (0.29 g, 4.62 mmol), K ₂ CO ₃ (6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and then stirred at 190 ° C for 12 hours.

After completion of the reaction, nitrobenzene was removed, and 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 the water had been removed, and the residue was purified by column chromatography to obtain Compound C-1 (12.14 g, yield: 37%).

GC-Mass (calculated: 710.86 g / mol, measured: 710 g / mol)

[Synthesis Example 2] Synthesis of Compound C-2

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine (17.29 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, 1, the compound C-2 (17.42 g, yield: 59%) was obtained.

GC-Mass (calculated: 639.75 g / mol, measured: 639 g / mol)

[Synthesis Example 3] Synthesis of Compound C-3

The procedure of Synthesis Example 1 was repeated except that 2-bromo-4,6-diphenylpyrimidine (17.24 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, C-3 (16.81 g, yield: 57%).

GC-Mass (theory: 638.76 g / mol, measurement: 638 g / mol)

[Synthesis Example 4] Synthesis of Compound C-4

The procedure of Synthesis Example 1 was repeated except that 2-bromo-6-phenylpyridine (12.97 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, 4 (17.37 g, yield: 67%).

GC-Mass (calculated: 561.67 g / mol, measured: 561 g / mol)

[Synthesis Example 5] Synthesis of Compound C-5

The procedure of Synthesis Example 1 was repeated except that 4-bromo-N, N-diphenylaniline (17.96 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, C-5 (18.35 g, yield: 61%).

GC-Mass (calculated: 651.80 g / mol, measured: 651 g / mol)

[Synthesis Example 6] Synthesis of Compound C-6

The same procedure as in Synthesis Example 1 was carried out except that (4-bromophenyl) triphenylsilane (23.01 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, (9.94 g, yield: 29%).

GC-Mass (calculated: 742.98 g / mol, measured: 742 g / mol)

[Synthesis Example 7] Synthesis of Compound C-7

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (21.50 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 , The same procedure as in Synthesis Example 1 was conducted to obtain Compound C-7 (23.13 g, yield: 70%).

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 8] Synthesis of Compound C-8

(4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 (20.11 g, yield: 55%) was obtained by carrying out the same processes as in the above Synthesis Example 1, except that the starting material (25.72 g, 55.40 mmol) was used.

GC-Mass (theory: 791.94 g / mol, measured: 791 g / mol)

[Synthesis Example 9] Synthesis of Compound C-9

The procedure of Synthesis Example 1 was repeated except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (21.45 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 To thereby give 21.9 g (yield: 64%) of the compound C-9.

GC-Mass (calculated: 714.85 g / mol, measured: 714 g / mol)

[Synthesis Example 10] Synthesis of Compound C-10

The same procedure as in Synthesis Example 2 was carried out except that IC-2 (15.34 g, 46.17 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 2 to obtain Compound C-10 20.55 g, yield: 56%).

GC-Mass (calculated: 794.90 g / mol, measured: 794 g / mol)

[Synthesis Example 11] Synthesis of Compound C-11

(C-11) was obtained in the same manner as in Synthesis Example 2, except that IC-3 (18.76 g, 46.17 mmol) synthesized in Preparation Example 3 was used instead of the compound IC- 12.36 g, yield: 42%).

GC-Mass (calculated: 637.73 g / mol, measured: 637 g / mol)

[Synthesis Example 12] Synthesis of Compound C-12

The same procedure as in Synthesis Example 2 was carried out except that IC-4 (15.25 g, 46.17 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 2 to obtain Compound C-12 18.66 g, yield: 51%).

GC-Mass (calculated: 792.89 g / mol, measured: 792 g / mol)

[Synthesis Example 13] Synthesis of Compound C-13

The same procedure as in Synthesis Example 2 was carried out except that IC-5 (16.04 g, 46.17 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 2 to obtain Compound C-13 11.75 g, yield: 44%).

GC-Mass (calculated: 578.68 g / mol, measured: 578 g / mol)

[Synthesis Example 14] Synthesis of Compound C-14

The same procedure as in Synthesis Example 2 was carried out except that IC-6 (15.30 g, 46.17 mmol) synthesized in Preparation Example 6 was used instead of Compound IC-1 used in Synthesis Example 2 to obtain Compound C-14 14.02 g, yield: 54%).

GC-Mass (calculated: 562.62 g / mol, measured: 562 g / mol)

[Examples 1 to 14] Fabrication of organic EL device

Compounds C-1 to C-14 synthesized in Synthesis Example 1-14 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) 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-14 + 10% Ir (ppy) ₃ (300 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] Fabrication of organic EL device

An 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 current densities of 10 mA / cm 2 were measured for each of the organic EL devices manufactured in Examples 1-14 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage EL peak Current efficiency (V) (nm) (cd / A) Example 1 C-1 6.68 517 40.9 Example 2 C-2 6.85 517 40.9 Example 3 C-3 6.66 516 42.1 Example 4 C-4 6.71 515 41.2 Example 5 C-5 6.7 518 42.2 Example 6 C-6 6.75 518 41.1 Example 7 C-7 6.64 516 43.5 Example 8 C-8 6.75 518 39.1 Example 9 C-9 6.65 517 41.7 Example 10 C-10 6.66 515 42.8 Example 11 C-11 6.87 516 41.1 Example 12 C-12 6.63 516 40.6 Example 13 C-13 6.81 517 40.6 Example 14 C-14 6.88 518 41.2 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL device of Example 1-14 using the compounds (C-1 to C-14) according to the present invention as a light emitting layer of a green organic EL device had a comparative example 1 &lt; / RTI &gt; green organic EL device.

Claims (7)

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

In Formula 1,
X ₁ is selected from the group consisting of N (Ar ₂ ), O, S, C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );
Y ₁ is a non-bonded or a single bond;
Ar ₁ to Ar ₆ 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 ₁₂ are the same or different and each independently 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 alkene 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 C _An arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and a substituted or unsubstituted arylsilyl group having ₆ to ₄₀ carbon atoms, or they may be bonded to adjacent groups to form a condensed ring,
In the Ar ₁ to Ar ₆ and R ₁ to R ₁₂ , 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 nucleus A heteroaryl group having 5 to 40 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 nucleus A heterocyclic alkyl group having 3 to 40 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 group, C ₆ to C ₄₀ arylphosphine oxide groups and C ₆ to C ₄₀ arylsilyl groups 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 ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, having 3 to 40 nuclear atoms of the heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₄₀ group, and A C ₆ to C ₄₀ arylsilyl group, and the like. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or Formula 3:
(2)

(3)

In this formula,
X ₁ , Ar ₁ And R ₁ to R ₁₂ are the same as defined in claim 1. _2. A compound according to claim 1, wherein X &lt; ₁ &gt; is N (Ar2). The compound according to claim 1, wherein each of Ar ₁ to Ar ₆ is independently a substituted or unsubstituted C ₆ to C ₄₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms,
A C ₆ ~ C ₄₀ aryl group, nuclear atoms groups are heteroaryl of 5 to 40 each independently represent a deuterium, a halogen, a cyano group, an alkenyl group of C ₁ ~ 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 _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl 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 arylamine group, ₄₀ of the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituted with one or more substituents selected from the group consisting of groups or Lt; / RTI &gt; is unsubstituted. The compound according to claim 1, wherein Ar ₁ to Ar ₆ And R &lt; ₁ &gt; to R &lt; ₁₂ &gt; are each independently selected from the group consisting of hydrogen or a substituent group consisting of the following S1 to S204.

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 at least one organic compound layer containing the compound is a light emitting layer.