KR20160037734A - A Plurality of Host Materials and An Organic Electroluminescent Device Comprising the Same - Google Patents

Abstract

The present invention relates to multiple types of host materials, and to an organic electroluminescent device comprising the same. The organic electroluminescent device of the present invention has high light emitting efficiency and excellent service life, by comprising specific combination of multiple types of host compounds.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a plurality of host materials and an organic electroluminescent device including the same,

The present invention relates to a plurality of kinds of host materials and an organic electroluminescent device including the same.

An electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast and fast response speed. In 1987, Eastman Kodak Company developed an organic electroluminescent device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

BACKGROUND ART An organic electroluminescent device (OLED) is an element that converts electric energy into light by applying electricity to an organic light emitting material. The organic electroluminescent device usually has a structure including an anode and a cathode and an organic layer between them. The organic material layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The material used for the organic material layer is classified into a hole injecting material, a hole transporting material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transporting material, and an electron injecting material. In this organic electroluminescent device, holes are injected from the anode into the light emitting layer, electrons from the cathode are injected into the light emitting layer, and excitons with high energy are formed by recombination of holes and electrons. This energy causes the light-emitting organic compound to be in an excited state, and the excited state of the light-emitting organic compound is returned to the ground state, and energy is emitted to the light to emit light.

The luminescent material of the organic electroluminescent device is the most important factor for determining the luminescent efficiency of the device. The luminescent material should have a high quantum efficiency and a high mobility of electrons and holes, and the formed luminescent material layer should be uniform and stable. Such a light emitting material is divided into a blue, green or red light emitting material depending on a luminescent color, and further, there is a yellow or orange light emitting material. Further, the luminescent material can be divided into a host material and a dopant material in terms of function. Recently, development of a high efficiency and long-life organic electroluminescent device has emerged as an urgent task. Especially, in consideration of the EL characteristic level required for a medium to large-sized OLED panel, it is urgent to develop a material superior to the conventional luminescent material . For this purpose, the desirable characteristics of the host material acting as a solid state solvent and energy transfer agent should be high purity and have a proper molecular weight to enable vacuum deposition. In addition, the glass transition temperature and thermal decomposition temperature must be high to ensure thermal stability, high electrochemical stability is required for longevity improvement, amorphous thin film must be easy to form, and adhesion to other adjacent layers is good, You should not.

The light emitting material can be used by mixing a host and a dopant to improve color purity, luminescence efficiency and stability. In general, a device having excellent EL characteristics is a structure including a light emitting layer made by doping a host with a dopant. When using such a dopant / host material system, the selection is important because the host material has a significant effect on the efficiency and lifetime of the light emitting device.

Korean Patent Laid-Open Publication No. 10-2008-0080306 and International Publication No. WO 2013/112557 disclose an organic electroluminescent device using a biscarbazole derivative as a host material. However, when a compound having a structure in which two rings are fused to one of the benzene rings constituting the carbazole and the N of the carbazole is linked with aryl or heteroaryl is used as a host material together with the biscarazole derivative, Is not specifically disclosed.

Korean Patent Laid-Open Publication No. 10-2008-0080306 (published on September 3, 2008) International Publication No. WO 2013/112557 A1 (published on August 1, 2013)

An object of the present invention is to provide an organic electroluminescent device having a long lifetime while maintaining a high luminous efficiency.

As a result of an intensive study to solve the above technical problems, the present inventors have found that the present inventors have found that an organic electroluminescent device comprising a cathode, a cathode, and an organic layer between the anode and the cathode; Wherein the organic material layer comprises one or more light emitting layers; Wherein at least one of the light emitting layers comprises at least one dopant compound and at least two host compounds; It has been found that the first host compound of the host compound is a compound represented by the following formula 1 and the second host compound is a compound represented by the following formula 2 to accomplish the above object and completed the present invention .

[Chemical Formula 1]

In Formula 1,

A ₁ and A ₂ are each independently substituted or unsubstituted (C 6 -C 30) aryl, with the proviso that the substituents of A ₁ and A ₂ are not nitrogen-containing heteroaryls;

L ₁ is a single bond or substituted or unsubstituted (C 6 -C 30) arylene;

X ₁ to X ₁₆ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 membered heteroaryl, substituted or unsubstituted Substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di- (C6-C30) arylamino; Adjacent substituents may be connected to each other to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring;

(2)

In Formula 2,

Ar ₁ is substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C6-C30) aryl;

L ₂ is a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

이고;Ring A ego; Ring B is

ego;

Y is O, S, C (R ₄ ) (R ₅ ) or N (R ₆ ); X is _{O, S, C (R 7} ) (R 8) or N (R _6), and;

Provided that when X and Y are simultaneously N (R < ₆ >), they are excluded;

R ₁ Wherein each of R ₁ to R ₃ is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 3 -C 30) Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted ) Heteroaryl, -NR ₉ R _10, or -SiR ₁₁ R ₁₂ R _13, or (C3-C30) monosubstituted or polycyclic alicyclic or aromatic rings substituted or unsubstituted with adjacent substituents;

R ₄ to R ₁₃ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5-7 membered) heterocycloalkyl, _{NR 14 R 15, -SiR 16 R} 17 R 18, cyano, nitro or hydroxy, or, which can form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring together with the adjacent substituent ;

R ₁₄ to R ₁₈ have the same definitions as R ₄ to R ₁₃ ;

The carbon atom of the alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

Wherein said heteroaryl (s) and heterocycloalkyl each independently comprise one or more heteroatoms selected from B, N, O, S, Si and P;

a, b and c are each independently an integer of 1 to 4; When a, b, or c is an integer of 2 or more, each R ₁ , R ₂ , or R ₃ may be the same or different.

According to the present invention, an organic electroluminescent device having high efficiency and long life is provided, and a display device or a lighting device using the same can be manufactured.

The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.

The organic electroluminescent device comprising the compounds represented by the above formulas (1) and (2) will be described in more detail as follows.

The term "(C 1 -C 30) alkyl" as used herein means straight-chain or branched alkyl having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30) alkenyl" means straight or branched chain alkenyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, "(C2-C30) alkynyl" means straight or branched chain alkynyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. The term "(C3-C30) cycloalkyl" as used herein means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term " (3-7 member) heterocycloalkyl "as used herein refers to a heterocycloalkyl group having 3 to 7, preferably 5 to 7, ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, Means a cycloalkyl containing one or more heteroatoms selected from atoms, preferably O, S and N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. The term "(C6-C30) aryl (phenylene)" as used herein refers to a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms in the ring is 6 to 20, 15 < / RTI > Examples of such aryls include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, , Fluoranthenyl, and the like. The term "(3-30) heteroaryl" as used herein means an aryl group containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P having 3 to 30 ring skeletal atoms . Here, the number of the atoms of the ring skeleton is preferably 5 to 20, more preferably 5 to 18. The number of heteroatoms is preferably 1 to 4. The heteroaryls herein may be monocyclic or fused ring systems condensed with one or more benzene rings and may be partially saturated. Also, the heteroaryl includes a form in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, "nitrogen-containing heteroaryl" means heteroaryl containing at least one nitrogen as a heteroatom. Examples of the nitrogen-containing heteroaryl include monocyclic heteroaryls such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, , And fused with benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, And heteroaryl heteroaryl. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Also, in the term "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. Substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted aryl (phenylene), substituted heteroaryl (substituted), substituted aralkyl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, Substituted mono-or di-arylamino, substituted monocyclic or polycyclic alicyclic or aromatic rings, substituted cycloalkenyl, substituted heterocycloalkyl, and substituted nitrogen-containing heteroaryl substituents are each independently selected from the group consisting of deuterium (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (3-30 membered heteroaryl or tri (C6-C30) arylsilyl which is unsubstituted or substituted by (C6-C30) aryl, (C3-30) (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, di (C1- (C6-C30) arylsilyl, amino, mono- or di- (C1-C30) alkylamino, mono- or di- (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C1-C30) alkyl (C6-C30) arylcarbonyl, (C6-C30) aryl Or more.

According to one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following Formulas 3, 4, 5, and 6.

(3)        [Chemical Formula 4]

[Chemical Formula 5]       [Chemical Formula 6]

In the above formulas 3 to 6,

A ₁ , A ₂ , L ₁ and X ₁ to X ₁₆ are as defined in formula (1).

Preferably, each of A ₁ and A ₂ is independently a substituted or unsubstituted (C 6 -C 18) aryl, and each independently is cyano, halogen, (C 1 -C 6) alkyl, (C 6 -C 12) C6-C12) arylsilyl-substituted or unsubstituted (C6-C18) aryl. Specifically, A ₁ and A ₂ each independently represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted Substituted or unsubstituted benzenesulfonyl, fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted indenyl, substituted or unsubstituted triphenylenyl, Substituted or unsubstituted pyrenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted creicenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, and Substituted or unsubstituted fluoranthenyl, and substituted or unsubstituted fluoranthenyl. (C6-C12) aryl, or tri (C6-C12) arylsilyl, wherein the substituted phenyl or the like may be cyano, halogen, (C1-C6) alkyl,

X ₁ to X ₁₆ each independently represent hydrogen, cyano, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, substituted or unsubstituted Heteroaryl, or substituted or unsubstituted tri (C6-C12) arylsilyl. Each of X ₁ to X ₁₆ is independently hydrogen; Cyano; (C1-C10) alkyl; (C6-C20) aryl unsubstituted or substituted with cyano, (C1-C10) alkyl or tri (C6-C12) arylsilyl; (5-20 membered) heteroaryl, unsubstituted or substituted with (C1-C10) alkyl, (C6-C15) aryl or tri (C6-C12) arylsilyl; Or a tri (C6-C12) arylsilyl which is unsubstituted or substituted by (C1-C10) alkyl. Specifically, each of X ₁ to X ₁₆ independently represents hydrogen; Cyano; (C1-C6) alkyl; Phenyl, biphenyl, terphenyl, or naphthyl, substituted or unsubstituted with cyano, (C1-C6) alkyl or triphenylsilyl; (C1-C6) alkyl, phenyl, biphenyl, naphthyl, or triphenylsilyl, dibenzothiophenyl or dibenzofuranyl; Or triphenylsilyl substituted or unsubstituted with (C1-C6) alkyl.

It is preferable that L ₁ is a single bond or a substituted or unsubstituted (C6-C30) arylene, a single bond, or a substituted or unsubstituted (C6-C15) arylene.

Specifically, L ₁ may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene. More specifically, L < ₁ > may be a single bond or may be represented by one of the following formulas (7) to (19).

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12]

[Chemical Formula 13]         [Chemical Formula 14]

[Chemical Formula 18] [Chemical Formula 19]

In the above formulas (7) to (19)

은 연결 위치를 나타낸다.Xi to Xp are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2- Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri Substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di ) Alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di- (C6-C30) arylamino; Adjacent substituents may be connected to each other to form a substituted or unsubstituted monocyclic or polycyclic alicyclic or aromatic ring of (C3-C30), and the carbon atom of the alicyclic or aromatic ring formed may be nitrogen, oxygen, and sulfur Lt; / RTI >;

Represents a connection position.

Preferably, Xi to Xp are each independently selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 10) alkyl, (C 3 -C 20) cycloalkyl, (C 6 -C 12) aryl, -C12) arylsilyl, or tri (C6-C12) arylsilyl; More preferably each independently hydrogen, cyano, (CrC6) alkyl, or tri (C6-C12) arylsilyl.

According to one embodiment of the present invention, the compound of formula (2) may be represented by any of the following formulas (20) to (23).

[Chemical Formula 20]

[Chemical Formula 22]

In the above Formulas 20 to 23, the definitions of Ar ₁ , L _{2 ,} X, Y, R ₁ to R ₃ , a, b and c are the same as those defined in Formula 2 above.

Ar ₁ is preferably a substituted or unsubstituted (5-20 membered) heteroaryl, more preferably a substituted or unsubstituted nitrogen containing (5-20 membered) heteroaryl. Ar ₁ is specifically substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted pyridinyl, Substituted or unsubstituted quinazolinyl, substituted or unsubstituted naphthyridinyl, and substituted or unsubstituted quinoxalinyl, and more specifically may be selected from the group consisting of substituted or unsubstituted quinazolinyl, Substituted or unsubstituted thiazolyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl. The substituent of Ar ₁ may be preferably (C 6 -C 20) aryl or (5-20) heteroaryl, and specifically includes phenyl, naphthyl, biphenyl, benzofuranyl, benzothiophenyl, dibenzo Furanyl, and dibenzothiophenyl. ≪ / RTI >

The L ₂ may preferably be a single bond, a substituted or unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (5-20 membered) heteroarylene; More preferably a single bond, or a substituted or unsubstituted (C6-C20) arylene. Specifically, L ₂ may be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

Preferably, X and Y are each independently selected from O, S, and N (R ₆ ) with the proviso that X and Y are not simultaneously N (R ₆ ). According to one embodiment of the present invention, X and Y may each independently be selected from O and S. According to another embodiment of the present invention, X and Y may each independently be selected from O and S, and at least one of X and Y may be S. The R ₆ may be preferably a substituted or unsubstituted (C 6 -C 30) aryl, specifically a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted biphenyl have.

Wherein R ₁ to R ₃ is preferably (C6-C30) each independently represent hydrogen, substituted or unsubstituted (C1-C20) alkyl, (C3-C20) substituted or unsubstituted cycloalkyl, substituted or unsubstituted Aryl, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₉ R ₁₀ or -SiR ₁₁ R ₁₂ R _13, or a (C3-C30) monocyclic or polycyclic Alicyclic or aromatic ring. The R ₉ to R ₁₃ may be preferably a substituted or unsubstituted (C 6 -C 30) aryl. The R ₁ to R ₃ may be specifically hydrogen.

The first host compound represented by Formula 1 may be exemplified as the following compounds, but is not limited thereto.

The second host compound represented by Formula 2 may be exemplified as the following compounds, but is not limited thereto.

The compound of Formula 1 and the compound of Formula 2 of the present invention can be easily prepared by a synthesis method known to a person skilled in the art. For example, the compound of formula (2) may be prepared by preparing a compound represented by the formula (A) shown below and then by bromination to produce a compound represented by the formula (B), and adding an indene ring, , A benzofuran ring, or a benzothiophene ring, and then introducing * -L ₂ -Ar ₁ to the prepared mother nucleus.

[Chemical Formula A]

In Formulas A and B above, Y is O, S, C (R ₄ ) (R ₅ ) or N (R ₆ ); X is O, S, a _{C (R 7) (R 8} ) or N (R _6).

The method for preparing the parent compound of the compound of formula 2 of the present invention described above can be illustrated by the following reaction formulas 1 to 4.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

[Reaction Scheme 4]

In the above Reaction Schemes 1 to 4, X may be selected from O, S, C (R ₇ ) (R ₈ ), and N (R ₆ ).

An organic electroluminescent device according to the present invention includes a cathode, a cathode, and an organic layer between the anode and the cathode; Wherein the organic material layer comprises one or more light emitting layers; Wherein at least one of the light emitting layers comprises at least one dopant compound and at least two host compounds; Wherein the first host compound of the host compound is a compound represented by the formula (1) and the second host compound is a compound represented by the formula (2).

The light emitting layer is a layer in which light is emitted. The doping concentration of the dopant compound with respect to the host compound in the light emitting layer is preferably less than 20% by weight. In the organic electroluminescent device of the present invention, the weight ratio of the first host compound to the second host compound ranges from 1:99 to 99: 1.

The organic material layer may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron buffer layer, an interlayer, a hole blocking layer and an electron blocking layer .

The dopant included in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) And more preferably an ortho-metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and still more preferably an orthometallated iridium complex compound.

The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following Chemical Formulas (101) to (103).

(101)            ≪ EMI ID =

In the above formulas (101) to (103)

L is selected from the following structures;

R ₁₀₀ is hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl;

R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) Unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₆ to R ₁₀₉ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, Or dibenzofuran which is substituted or unsubstituted with alkyl is possible; R ₁₂₀ to R ₁₂₃ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, quinoline substituted or unsubstituted with alkyl or aryl;

R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; R ₁₂₄ to R ₁₂₇ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, Or dibenzofuran which is substituted or unsubstituted with alkyl is possible;

R ₂₀₁ to R ₂₁₁ each independently represents hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, or substituted or unsubstituted -30) aryl, and R < ₂₀₈ &_gt; to R < ₂₁₁ &_gt; may be connected to adjacent substituents to form a substituted or unsubstituted fused ring. For example, fluorine, substituted or unsubstituted alkyl, Substituted dibenzothiophene or dibenzofuran substituted or unsubstituted alkyl;

f and g are each independently an integer of 1 to 3; When f or g is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other;

n is an integer of 1 to 3;

Specific examples of the phosphorescent dopant material are as follows.

The organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in the organic material layer.

Further, in the organic electroluminescent device of the present invention, it is preferable that the organic material layer contains one or more metals selected from the group consisting of Group 1, Group 2, and 4 period transition metals, 5 period transition metals, lanthanide series metals and d- , Or one or more complex compounds comprising such metals.

In the organic electroluminescent device of the present invention, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer"Quot;). Concretely, it is preferable to arrange a layer of a chalcogenide (including an oxide) of silicon and aluminum on the surface of the anode on the side of the light emitting medium layer and a metal halide layer or metal oxide layer on the surface of the cathode on the side of the light emitting medium layer. The driving layer of the organic electroluminescent device can be stabilized by the surface layer. Preferable examples of the chalcogenide include SiO _x (1? _X ? 2), AlO _x (1? X? 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , and rare earth fluoride. Preferred examples of the metal oxide include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, and CaO.

A layer selected from a hole injection layer, a hole transporting layer, or an electron blocking layer or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be formed of a plurality of layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each layer may use two or more compounds at the same time. A plurality of layers may also be used for the hole transporting layer or the electron blocking layer.

A layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may use a plurality of layers for the purpose of controlling the electron injection and improving the interface characteristics between the light emitting layer and the electron injecting layer, and each layer may use two or more compounds at the same time. A plurality of layers may be used as the hole blocking layer or the electron transporting layer, and a plurality of compounds may be used for each layer

In the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant, on at least one surface of the pair of electrodes. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The present invention further provides a material for manufacturing an organic electroluminescent device in a further aspect. The material includes the compound represented by the formula (1) and the compound represented by the formula (2). Specifically, the material may be a material for manufacturing the light emitting layer of the organic electroluminescence device, more specifically, a host material for the light emitting layer of the organic electroluminescence device. The material may be in the form of a composition or a mixture. The material may further comprise conventional materials included in the organic electroluminescent material.

The formation of the respective layers of the organic electroluminescent device of the present invention can be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, ink jet printing, nozzle printing, slot coating, , Spin coating, dip coating, and flow coating may be used. When the first host compound and the second host compound of the present invention are formed, they are subjected to co-deposition or mixed deposition.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., And it may be any thing that does not have a problem in the tabernacle.

In the organic electroluminescent device of the present invention, two or more host compounds of the light emitting layer may be co-deposited or mixed-deposited. The co-deposition is a method in which two or more materials are placed in respective individual crucible sources and a current is applied to each cell at the same time to vaporize the material to perform mixed deposition. The mixed deposition is a method in which two or more materials are deposited on one crucible source After mixing, a current is applied to one cell to evaporate the material and mix it.

Further, it is possible to manufacture a display device or a lighting device using the organic electroluminescent device of the present invention.

Hereinafter, the method for preparing the host compound of the present invention and the luminescent characteristics of the device containing the compound will be described in order to understand the present invention in detail.

[ Example  1] Preparation of compounds C-1 and C-7

Preparation of Compound 1-1

To the reaction vessel were added 4-bromodibenzothiophene (50 g, 189.98 mmol), 2-methylthiophenylboronic acid (31.9 g, 189.89 mmol), tetrakis (triphenylphosphine) palladium (11 g, 9.499 mmol) (60 g, 569.94 mmol), toluene (900 mL), ethanol (280 mL) and distilled water (280 mL) were added, followed by stirring at 120 ° C for 3 hours. After the reaction was completed, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 1-1 (58 g, 99%).

Preparation of Compound 1-2

Compound 1-1 (58 g, 189.98 mmol) was dissolved in tetrahydrofuran (THF) (500 mL) and acetic acid (580 mL) and hydrogen peroxide (35%) (23 mL) was slowly added dropwise. After stirring for 10 hours at room temperature, the reaction mixture was concentrated to remove the solvent. The organic layer was extracted with dichloromethane and purified water. The organic layer was dried over magnesium sulfate to remove residual water, concentrated, and immediately subjected to the next reaction Respectively.

Preparation of compounds 1-3

Compound 1-2 (58 g) was dissolved in trifluoromethanesulfonic acid (300 mL), stirred at room temperature for 2 days, added dropwise to a solution of pyridine (600 mL) / purified water (1.5 mL) Lt; / RTI > When the reaction was completed, the organic layer was extracted with dichloromethane and separated into a column to obtain Compound 1-3 (15.4 g, 28%).

Preparation of compounds 1-4

Compound 1-3 (15.4 g, 53.03 mmol) was dissolved in chloroform (550 mL), cooled to 0 ° C, and bromine (2.7 mL, 53.03 mmol) was slowly added dropwise. When the addition was completed, the temperature was gradually raised to room temperature and stirred for 8 hours. After completion of the reaction, bromine was removed from the aqueous solution of sodium thiosulfate and filtered to obtain Compound 1-4 (12.8 g, 65.4%).

Preparation of compounds 1-5

Butylphosphine (50%) (1.4 mL, 2.77 mmol) and sodium (0.45 g, 45.06 mmol) were added to a solution of the compound 1-4 (12.8 g, 34.66 mmol), chloroaniline (4.7 mL, 45.06 mmol), palladium acetate t-Butoxide (8.3 g, 86.65 mmol) was added to toluene (170 mL), and the mixture was refluxed overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and the organic layer was extracted with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure and then purified by column chromatography to obtain Compound 1-5 (13.7 g, 77%).

Preparation of compounds 1-6

A reaction vessel compound 1-5 (13.7g, 32.94mmol), palladium acetate (0.4g, 1.646mmol), tricyclo-hexyl phosphonium tetrafluoroborate _{(C 18 H 34 P.BF 4)} (1.21g, 3.29mmol ), Cesium carbonate (32.1 g, 98.82 mmol) and dimethylacetamide (DMA) (250 mL) were added thereto, followed by stirring at 180 ° C for 7 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. The organic layer was distilled under reduced pressure and then purified by column chromatography to obtain Compound 1-6 (5.6 g, 45%).

Preparation of Compound C-1

(5 g, 13.17 mmol), compound 1-7 (4.6 g, 15.81 mmol), palladium acetate (1.2 g, 5.27 mmol), 50% t- butylphosphine (5 mL, 10.54 mmol) and cesium carbonate 13g, 39.5mmol) was dissolved in toluene (65mL) and refluxed at 130 DEG C for 3 hours. When the reaction was completed, the organic layer was extracted with dichloromethane / purified water and separated into a column to obtain Compound C-1 (4.4 g, 57%).

UV: 319 nm, PL: 525 nm, melting point: 261 캜, MS / EIMS measured value 584; Calculated 583

Preparation of Compound C-7

The compound 1-6 (1.6 g, 4.21 mmol) and the compound 1-8 (1.7 g, 6.32 mmol) were dissolved in 30 ml of dimethylformamide and NaH (0.5 g, 12.63 mmol, 60% ). The mixture was stirred at room temperature for 12 hours, and methanol and distilled water were added thereto. The resulting solid was filtered under reduced pressure and subjected to column separation to obtain Compound C-7 (1.4 g, 54%).

UV: 342 nm, PL: 528 nm, melting point: 360 占 폚, MS / EIMS measurement value 611; Calculated value 610

 [ Example  2] Preparation of compounds C-13 and C-19

Preparation of Compound 2-1

The reaction vessel was charged with 4-bromodibenzofuran (50 g, 202.35 mmol), 2-methylthiophenylboronic acid (34 g, 202.35 mmol), tetrakis (triphenylphosphine) palladium (11.7 g, 10.117 mmol) 64 g, 607.06 mmol), toluene (1,000 mL), ethanol (300 mL) and distilled water (300 mL) were added, followed by stirring at 120 ° C for 3 hours. After the reaction was completed, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 2-1 (58 g, 99%).

Preparation of Compound 2-2

Compound 2-1 (58 g, 202.35 mmol) was dissolved in THF (580 mL) and acetic acid (580 mL) and hydrogen peroxide (35%) (26 mL) was slowly added dropwise. After stirring for 10 hours at room temperature, the reaction mixture was concentrated to remove the solvent. The organic layer was extracted with dichloromethane and purified water. The organic layer was dried over magnesium sulfate to remove residual water, concentrated, and then immediately reacted .

Preparation of Compound 2-3

Compound 2-2 was added dropwise to a solution of pyridine (600 mL) / purified water (1.5 mL), and the mixture was heated to reflux at 120 캜 for 4 hours. When the reaction was completed, the organic layer was extracted with dichloromethane and separated into a column to obtain Compound 2-3 (48.6 g, 93%).

Preparation of compound 2-4

Compound 2-3 (43.6 g, 158.9 mmol) was dissolved in chloroform (800 mL), cooled to 0 ° C, and bromine (8.55 mL, 166.87 mmol) was slowly added dropwise. When the addition was completed, the temperature was gradually raised to room temperature and stirred for 8 hours. After completion of the reaction, the bromine was removed from the aqueous solution of sodium thiosulfate, followed by filtration to obtain the compound 2-4 (44 g, 70%).

Preparation of Compound 2-5

Butylphosphine (50%) (2.2 mL, 4.53 mmol) and sodium t (2-ethylhexanoate) were added to a solution of 2-4 (20 g, 56.62 mmol), chloroaniline (7.7 mL, 73.61 mmol), palladium acetate -Butoxide (13.6 g, 141.55 mmol) were added to toluene (280 mL), and the mixture was refluxed and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and the organic layer was extracted with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure and then purified by column chromatography to obtain Compound 2-5 (11 g, 48.6%).

Preparation of Compound 2-6

A reaction vessel Compound 2-5 (11g, 27.5mmol), palladium acetate _{(0.3g, 1.37mmol), C 18} H 34 P.BF 4 (1g, 2.75mmol), cesium carbonate (26g, 82.5mmol) and DMA ( 135 mL) was added thereto, followed by stirring at 180 ° C for 7 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain 2-6 (4 g, 40%).

Preparation of Compound C-13

Compound 2.7 g (11.55 mmol), palladium acetate (0.86 g, 3.85 mmol), 50% t-butylphosphine (3.7 mL, 7.704 mmol) and cesium Carbonitrile (9.4 g, 28.8 mmol) was dissolved in toluene (100 mL), and the mixture was refluxed at 130 DEG C for 3 hours. After the reaction was completed, the organic layer was extracted with dichloromethane / purified water and separated into a column to obtain a compound C-13 (2.5 g, 46%).

UV: 296 nm, PL: 535 nm, melting point: 290 캜, MS / EIMS measured value 568; Calculated value 567

Preparation of Compound C-19

Compound 2-6 (3g, 8.2mmol) and Compound 1-8 (2.65g, 9.9mmol) were dissolved in dimethylformamide (DMF) (40mL) and NaH (1g, 24.76mmol, 60% in mineral oil) . The mixture was stirred at room temperature for 12 hours, and methanol and distilled water were added thereto. The resulting solid was filtered under reduced pressure and subjected to column separation to obtain Compound C-19 (3.1 g, 63%).

UV: 342 nm, PL: 532 nm, melting point: 353 캜, MS / EIMS measurement value 595; Calculated value 594

[ Example  3] Compound C- Twenty  Produce

One) Synthesis of Compound 1-1

To the flask, add benzo [b] [1] benzocano [2,3-g] benzofuran (30 g, 109 mmol) and chloroform (540 mL) Then, bromine (5.8 mL, 114 mmol) was slowly added dropwise and stirred for 3 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain Compound 1-1 (23 g, yield: 60%).

2) Synthesis of Compound 1-2

To a flask was added compound 1-1 (18 g, 52.1 mmol), 2-chloroaniline (8.2 mL, 78.1 mmol), palladium acetate (1.1 g, 5.21 mmol), tri- tert- butylphosphine (5 mL mmol), sodium tert-butoxide (15 g, 156 mmol) and toluene (260 mL) were stirred at reflux for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and dried with magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain Compound 1-2 (18 g, yield: 90%).

3) Synthesis of Compound 1-3

The flask compound 1-2 (18g, 47.0 mmol), palladium acetate (1.0g, 4.70 mmol), tricyclo-hexyl jitsu flow tetra borate (3.4g, 9.40 mmol), cesium carbonate (46 g, 141 mmol) and dimethyl (240 mL) was stirred at reflux for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and dried with magnesium sulfate. The residue was subjected to vacuum distillation and column separation to obtain Compound 1-3 (6.7 g, yield: 40%).

3) Synthesis of Compound C-20

Compound 3 (3 g, 8.25 mmol) Compound B (3.4 g, 10.7 mmol) was dissolved in dimethylformamide (DMF) (40 mL) and NaH (60 g in 24.76 mmol, mineral oil) Respectively. The mixture was stirred at room temperature for 12 hours, and methanol and distilled water were added thereto. The resulting solid was filtered under reduced pressure and subjected to column separation to obtain Compound C-20 (3.6 g, 67%).

Molecular weight (MW) 644.74, UV: 344 nm, PL: 535 nm, melting point 378 DEG C

 [ Example  4] Preparation of Compound C-22

One) Synthesis of Compound 1-1

To the flask, add benzo [b] [1] benzocano [2,3-g] benzofuran (30 g, 109 mmol) and chloroform (540 mL) Then, bromine (5.8 mL, 114 mmol) was slowly added dropwise and stirred for 3 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain Compound 1-1 (23 g, yield: 60%).

2) Synthesis of Compound 1-2

To a flask was added compound 1-1 (18 g, 52.1 mmol), 2-chloroaniline (8.2 mL, 78.1 mmol), palladium acetate (1.1 g, 5.21 mmol), tri- tert- butylphosphine (5 mL mmol), sodium tert-butoxide (15 g, 156 mmol) and toluene (260 mL) were stirred at reflux for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and dried with magnesium sulfate. The mixture was distilled under reduced pressure and subjected to column separation to obtain Compound 1-2 (18 g, yield: 90%).

3) Synthesis of Compound 1-3

The flask compound 1-2 (18g, 47.0 mmol), palladium acetate (1.0g, 4.70 mmol), tricyclo-hexyl jitsu flow tetra borate (3.4g, 9.40 mmol), cesium carbonate (46 g, 141 mmol) and dimethyl (240 mL) was refluxed with stirring for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and dried with magnesium sulfate. The residue was subjected to vacuum distillation and column separation to obtain Compound 1-3 (6.7 g, yield: 40%).

3) Synthesis of Compound C-22

To a flask was added Compound 1-3 (6.7 g, 18.4 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.8 g, 20.2 mmol) (0.9 g, 50%), 1.84 mmol), sodium tert-butoxide (4.4 g, 46.1 mmol) and toluene (100 mL, ) Was refluxed and stirred for 3 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and dried with magnesium sulfate. The residue was subjected to vacuum distillation and column separation to obtain Compound C-22 (8.3 g, yield: 67%).

Molecular weight: 670.78, UV: 390 nm, PL: 541 nm, melting point: 382 DEG C

[device Example  1-1 to 1-6] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (10? /?) On an OLED glass (manufactured by Geomatec) was subjected to ultrasonic cleaning using acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used. Next, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, HI-1 was placed in the cell in the vacuum deposition apparatus, the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr, And evaporated to deposit a hole injection layer 1 having a thickness of 80 nm on the ITO substrate. Subsequently, HI- 2 was placed in another cell in the vacuum evaporation apparatus, and a current was applied to the cell to evaporate it, thereby depositing a hole injection layer 2 having a thickness of 5 nm on the hole injection layer 1. Then, HT- 1 was added to another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate the hole transport layer 1 to deposit a hole transport layer 1 having a thickness of 10 nm on the hole injection layer 2. HT- 2 or HT- 3 was added to another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate the hole transport layer 1 to deposit a hole transport layer 2 having a thickness of 60 nm. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The first host compound and the second host compound described in Table 1 below were placed as a host in two cells in a vacuum deposition apparatus and the dopant substances listed in Table 1 were added to the other cells. : 1 at the same rate, and at the same time, the dopant material was evaporated at a different rate, and a dopant was doped to the total amount of the host and the dopant in an amount of 3 wt%, thereby depositing a light emitting layer with a thickness of 40 nm on the hole transport layer. Then, ET-1 and EI-1 were evaporated at a rate of 1: 1 in two other cells to deposit an electron transport layer with a thickness of 30 nm on the light emitting layer. Subsequently, EI- 1 was deposited to a thickness of 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm using another vacuum vapor deposition apparatus to fabricate an OLED device.

[ Comparative Example  1-1 to 1-4] containing only the second host compound as the host OLED  Device Manufacturing

OLED devices were manufactured in the same manner as in the device embodiments 1-1 to 1-6 except that only the second host of Comparative Examples 1-1 to 1-4 described in the following Table 1 was used as the host of the light emitting layer.

[ Comparative Example  2-1, 2-2] containing only the first host compound as the host OLED  Device Manufacturing

OLED devices were fabricated in the same manner as in the device embodiments 1-1 to 1-6 except that only the first host of Comparative Examples 2-1 to 2-2 described in the following Table 1 was used as the host of the light emitting layer.

The evaluation results of the organic electroluminescence devices manufactured in the Device Examples 1-1 to 1-6, Comparative Examples 1-1 to 1-4, and Comparative Examples 2-1 to 2-2 are shown in Table 1 below .

[Table 1]

According to the present invention, an organic electroluminescent device having a long life can be provided by using a plurality of kinds of hosts in comparison with a conventional device using one kind of host.

Claims (10)

An anode, a cathode, and an organic layer between the anode and the cathode; Wherein the organic material layer comprises one or more light emitting layers; Wherein at least one of the light emitting layers comprises at least one dopant compound and at least two host compounds; Wherein the first host compound of the host compound is a compound represented by the following Formula 1 and the second host compound is a compound represented by the following Formula 2.
[Chemical Formula 1]

In Formula 1,
A ₁ and A ₂ are each independently substituted or unsubstituted (C 6 -C 30) aryl, with the proviso that the substituents of A ₁ and A ₂ are not nitrogen-containing heteroaryls;
L ₁ is a single bond or substituted or unsubstituted (C 6 -C 30) arylene;
X ₁ to X ₁₆ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 2 -C 30) alkenyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 membered heteroaryl, substituted or unsubstituted Substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di- (C6-C30) arylamino; Adjacent substituents may be connected to each other to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring;
(2)

In Formula 2,
Ar ₁ is substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C6-C30) aryl;
L ₂ is a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
Ring A

ego; Ring B is

ego;
Y is O, S, C (R ₄ ) (R ₅ ) or N (R ₆ ); X is _{O, S, C (R 7} ) (R 8) or N (R _6), and;
Provided that when X and Y are simultaneously N (R < ₆ >), they are excluded;
R ₁ Wherein each of R ₁ to R ₃ is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 3 -C 30) Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted ) Heteroaryl, -NR ₉ R _10, or -SiR ₁₁ R ₁₂ R _13, or (C3-C30) monosubstituted or polycyclic alicyclic or aromatic rings substituted or unsubstituted with adjacent substituents;
R ₄ to R ₁₃ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5-7 membered) heterocycloalkyl, _{NR 14 R 15, -SiR 16 R} 17 R 18, cyano, nitro or hydroxy, or, which can form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring together with the adjacent substituent ;
R ₁₄ to R ₁₈ have the same definitions as R ₄ to R ₁₃ ;
The carbon atom of the alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
Wherein said heteroaryl (s) and heterocycloalkyl each independently comprise one or more heteroatoms selected from B, N, O, S, Si, and P;
a, b and c are each independently an integer of 1 to 4; When a, b, or c is an integer of 2 or more, each R ₁ , R ₂ , or R ₃ may be the same or different. The organic electroluminescent device according to claim 1, wherein the compound of Formula 1 is represented by any one of the following Formulas 3, 4, 5,
[Chemical Formula 3]

[Chemical Formula 5]

In the above formulas 3 to 6,
A ₁ , A ₂ , L ₁ and X ₁ to X ₁₆ are the same as defined in claim 1. The compound according to claim 1, wherein A ₁ and A ₂ each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted indenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted indenyl, Substituted or unsubstituted pyrenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted creicenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl , And substituted or unsubstituted fluoranthenyl. The organic electroluminescent device according to claim 1, wherein L ₁ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene. The organic electroluminescent device according to claim 1, wherein the compound of Formula 2 is represented by any one of the following Formulas 20 to 23.
[Chemical Formula 20]

[Chemical Formula 22]

In the above formulas 20 to 23, Ar ₁ , L _{2 ,} X, Y, R ₁ to R ₃ , a, b and c are the same as defined in claim 1. The compound according to claim 1, wherein Ar ₁ is substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl , Substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted naphthyridinyl, and substituted or unsubstituted quinoxalinyl. The organic electroluminescent device according to claim 1, wherein L ₂ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene. The organic electroluminescent device according to claim 1, wherein X and Y are each independently selected from O, S, and N (R ₆ ), except that X and Y are simultaneously N (R ₆ ). The organic electroluminescent device according to claim 1, wherein the compound of Formula 1 is selected from the following compounds.

The organic electroluminescent device according to claim 1, wherein the compound of Formula 2 is selected from the following compounds.