KR101472295B1 - Multicyclic aromatic compound and organic light emitting device including the same - Google Patents

Abstract

The present invention relates to a multi-cyclic aromatic compound and an organic electroluminescent device comprising the same. The present invention provides an organic electroluminescent device which exhibits excellent quantum efficiency as compared with a conventional compound for an organic electroluminescent device, A multicycle aromatic compound for an electroluminescent device and an organic electroluminescent device including the same are provided.

Description

TECHNICAL FIELD [0001] The present invention relates to a multi-ring aromatic compound and an organic electroluminescent device including the multi-

More particularly, the present invention relates to a multi-cyclic aromatic compound and an organic electroluminescent device including the multi-cyclic aromatic compound, which realize low-voltage driving and high-efficiency light emission characteristics when applied to an organic electroluminescent device.

The organic electroluminescent device has a simpler structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP) and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.

In general, when a direct current voltage is applied to an organic electroluminescent device, holes injected from the anode recombine with electrons injected from the cathode to form an electron-hole pair exciton, and the exciton returns to a stable ground state, It is converted into light by transmission to the material.

In order to improve the efficiency and stability of the organic electroluminescent device, a laminated organic thin film is formed between two opposing electrodes by CW Tang et al. Of Eastman Kodak Company, and a low voltage driven organic electroluminescent device is reported (CW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structure organic electroluminescent devices have been actively conducted. The efficiency and lifetime of such a stacked organic electroluminescent device are closely related to the molecular structure of the material constituting the thin film. For example, the quantum efficiency is greatly influenced by the structure of the host material, the hole transporting layer material, or the electron transporting layer material among the materials constituting the thin film, and when the thermal stability is deteriorated, the crystallization of the material occurs at a high temperature or a driving temperature, Is shortened.

As conventional multi-ring compounds, compounds having 6-membered ring-5-membered ring-6-membered rings in which hetero or non hetero aromatic rings are respectively bonded are fluorene, carbazole, dibenzofuran, dibenzothiophene and benzofuro Pyridine and the like are known. In particular, these compounds have high triplet energy and are known to have excellent properties in organic phosphorescent devices. However, there is a problem that it is difficult to expect improvement in characteristics from the efficiency and lifetime of the blue and green phosphorescent devices to a level that can be commercialized. Therefore, it is required to develop a new core structure which can improve the efficiency and lifetime of the device by improving the characteristics of the existing compound.

SUMMARY OF THE INVENTION Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and it is an object of the present invention to provide an organic electroluminescent device including a hole transporting material, a hole injecting material, a host material of a light emitting layer, an electron transporting material, To provide a multicyclic aromatic compound which exhibits improved driving voltage and excellent quantum efficiency.

A second object of the present invention is to provide a multi-ring aromatic compound having thermal stability and electrochemical stability of molecular structure.

A third object of the present invention is to provide an organic electroluminescent device including a multi-cyclic aromatic compound having a high quantum efficiency, a long driving life, and a high thermal stability and electrochemical stability.

 One embodiment of the present invention provides a multicycyclic aromatic compound for an organic electroluminescence device represented by the following structural formula (1).

[Structural formula 1]

 In formula 1,

The compound represented by Structural Formula 1 is fused in the order of a 6-membered ring structure (a), a 5-membered ring structure (b), a 6-membered ring structure (c), a 5-membered ring structure (d) Aromatic polycyclic aromatic compound,

X ¹ to X ¹⁴ may be the same or different from each other, X ¹ to X ¹⁴ are each independently a carbon atom or a nitrogen atom, X ¹ to X ¹⁴ Is a nitrogen atom,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기일 수 있고, R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring A heteroaryl group,

R ¹ and R ² are taken together with the carbon atoms of the adjacent six-membered ring structure (a) to form a substituted or unsubstituted C _6-30 fused aromatic ring or a substituted or unsubstituted C _2-30 fused hetero R ³ and R ⁴ may be combined with a carbon atom of the adjacent six-membered ring structure (c) to form a substituted or unsubstituted C _6-30 bonded aromatic ring or a substituted or unsubstituted C _2-30 , and R ⁵ and R ⁶ are taken together with the carbon atoms of the adjacent six-membered ring structure (e) to form a substituted or unsubstituted C ₆ -C _{30 -containing} conjugated heteroaromatic ring aromatic ring or may form a conjugated heteroaromatic ring of a substituted or unsubstituted C _{2 -30,}

R ⁷ to R ¹¹ may be the same or different from each other, and each of R ⁷ to R ¹¹ independently represents a hydrogen atom, a substituted or unsubstituted C _1-9 alkyl group, a substituted or unsubstituted C _5-30 alkyl group, A substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 heteroaryl group,

Ar ¹ to Ar ⁴ may be the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 heteroaryl group,

Y ¹ is an oxygen atom or a sulfur atom,

, 및

중에서 선택된 1종이고,L and M may be the same or different from each other, and L and M are each independently an oxygen atom, a sulfur atom,

, And

, And one

R ¹² to R ¹⁴ may be the same or different from each other, R ¹² to R ¹⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, A substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group,

R ¹² and R ¹⁴ may be each individually or together bonded to form a substituted or unsubstituted C ₆ -C ₃₀ saturated spiro ring or a substituted or unsubstituted C _{6 -30} unsaturated spiro ring,

The groups corresponding to " substitution " in Ar ¹ to Ar ⁴ and R ¹ to R ¹⁴ are each independently a halogen atom, a cyano group, a nitro group, an aryl group having _{5 to 30} carbon atoms, a heteroaryl group having _{2 to 30} carbon atoms, alkyl group of C _{1 -9,} alkyl ventilation of _{5 -30} C, a silyl group of C _{1 -30} thio, or C _{1 -30} of.

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode, wherein the organic material layer comprises the multi-cyclic aromatic compound according to claim 1, .

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises a host and a dopant, wherein the host comprises a multi-ring aromatic compound according to the present invention An organic electroluminescent device is provided.

The present invention provides a multi-ring aromatic compound having improved driving voltage and excellent quantum efficiency when applied to an organic electroluminescent device using a hole transporting material, a hole injecting material, a host material of a light emitting layer, an electron transporting material, and an electron injecting material .

The present invention also provides multicyclic aromatic compounds having thermal stability and electrochemical stability of molecular structure.

Further, the present invention can provide an organic electroluminescent device including a multicyclic aromatic compound and having high quantum efficiency, long driving life, and high thermal stability and electrochemical stability.

1 is a cross-sectional view of an organic electroluminescent device according to the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to the present invention.
3 is a graph showing a relationship between voltage and current of an organic electroluminescent device according to one embodiment of the present invention.
4 is a graph showing the relationship between the luminance and the quantum efficiency of an organic electroluminescent device according to an embodiment of the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will now be described more fully hereinafter with reference to the accompanying drawings, in which exemplary embodiments of the present invention are shown. The same reference numerals denote the same elements, and a duplicate description thereof will be omitted.

It is to be understood, however, that the following description is not intended to limit the invention to the particular embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

Furthermore, terms including an ordinal number such as the first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >

The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

Unless specifically stated otherwise in the present invention, a hydrogen atom is any one selected from the group consisting of hydrogen, H, a double hydrogen atom (deterium, D) and a tritium atom (T), preferably a monovalent hydrogen atom (hydrogen, H) and a double hydrogen atom (deterium, D), and more preferably a hydrogen atom (hydrogen, H).

As a technical means for achieving the above technical object, one aspect of the present invention provides a multicycyclic aromatic compound for an organic electroluminescence device, which is represented by the following structural formula 1.

[Structural formula 1]

 In formula 1,

The compound represented by Structural Formula 1 is fused in the order of a 6-membered ring structure (a), a 5-membered ring structure (b), a 6-membered ring structure (c), a 5-membered ring structure (d) Aromatic polycyclic aromatic compound,

X ¹ to X ¹⁴ may be the same or different from each other, X ¹ to X ¹⁴ are each independently a carbon atom or a nitrogen atom, X ¹ to X ¹⁴ Is a nitrogen atom,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기일 수 있고, R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring A heteroaryl group,

R ¹ and R ² are taken together with the carbon atoms of the adjacent six-membered ring structure (a) to form a substituted or unsubstituted C _{6 -30} bonded aromatic ring or a substituted or unsubstituted C _{2 -30} bonded hetero R ³ and R ⁴ may be combined with a carbon atom of the adjacent six-membered ring structure (c) to form a substituted or unsubstituted C _{6 -30} bonded aromatic ring or a substituted or unsubstituted to form a conjugated heteroaromatic ring of C and _{2 -30,} R ⁵ and R ⁶ combine with the carbon atom of the adjacent six-membered ring structure (e) with a substituted or unsubstituted C ₆ bond of _-30 aromatic ring or may form a conjugated heteroaromatic ring of a substituted or unsubstituted C _{2 -30,}

R ⁷ to R ¹¹ may be the same or different from each other, R ⁷ to R ¹¹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, A substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group,

Ar ¹ to Ar ⁴ may be the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted C _{2 -30} heteroaryl group,

Y ¹ is an oxygen atom or a sulfur atom,

, 및

중에서 선택된 1종이고,L and M may be the same or different from each other, and L and M are each independently an oxygen atom, a sulfur atom,

, And

, And one

R ¹² to R ¹⁴ may be the same or different from each other, R ¹² to R ¹⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, A substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 heteroaryl group,

R ¹² and R ¹⁴ are each independently or together bonded to form a substituted or unsubstituted C _6-30 saturated _spiro ring or a substituted or unsubstituted C _6-30 unsaturated _spiro ring,

The groups corresponding to " substitution " in Ar ¹ to Ar ⁴ and R ¹ to R ¹⁴ are each independently a halogen atom, a cyano group, a nitro group, an aryl group having _{5 to 30} carbon atoms, a heteroaryl group having _{2 to 30} carbon atoms, alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, a thio group, or a silyl group of C _1-30 of C _1-30.

In the present invention, more preferably, R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ are each independently a hydrogen atom, a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, And a phenyl group.

이고, In the present invention, more preferably, R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ represent hydrogen or

ego,

R ⁸ and R ⁹ may be the same or different from each other, and R ⁸ and R ⁹ may each independently be a hydrogen atom or a C _1-9 alkyl group.

이고, In the present invention, more preferably, R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ represent hydrogen or

ego,

Ar ¹ and Ar ² may be the same or different from each other, and each independently may be a hydrogen atom or a C _6-30 aryl group.

In the present invention, the chemical formula represented by the following structural formula 2, which is the central structure of the structural formula 1, may be one selected from the group consisting of the following Chemical Formulas 1 to 30.

[Structural formula 2]

In the structural formula 2 X ¹ to X ^14, L, M, 6-membered ring structures (a), 5-membered ring structure, (b), six-membered ring structures (c), 5-membered ring structures (d) and 6 member ring structures ( e) is the same as described in the structural formula 1.

[Chemical Formula 1 to 30]

 In the present invention, the compound represented by the above-mentioned 5-membered ring structure (b) may be one selected from the group consisting of furan, thiophene and pyrrole.

In the present invention, the compound represented by the five-membered ring structure (d) may be one selected from the group consisting of furan, thiophene and pyrrole.

Specific examples of the C _6-30 aryl group of R ¹ to R ¹⁴ and Ar ¹ to Ar ⁴ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, Naphthacene group, 2-naphthacene group, 9-naphthacene group, 3-phenanthryl group, 4-phenanthryl group, Biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, A m-tolyl group, an m-tolyl group, a p-terphenyl group, a p-terphenyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4-methyl-1-naphthyl group, Methylbiphenylyl group or 4-tert-butyl-p-terphenyl-4-yl group.

Specific examples of the C _2-30 heteroaryl group of R ¹ to R ¹⁴ and Ar ¹ to Ar ⁴ include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, pyrimidyl, Indolyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3- Isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a 6-isoindolyl group, a 6-isoindolyl group, A 2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, Isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, Diethyl, 3-dibenzofuranyl, 6-dibenzo Benzothiophene, 5-benzothiophene, 6-benzothiophene, 6-benzothiophene, 6-benzothiophene, Dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 6-dibenzothiophene, 7-dibenzothiophene, Benzophenone, benzothiophene, octene, 8-dibenzothiophene, 9-dibenzothiophene, 2-benzophosphole, Dibenzofuspol, 3-dibenzofospor, 4-iben zofospor, 6-iven zofospor, 7-dibenzofospor, 8-dibenzofospor, 9 -Benzoylphosphoric acid, 3-benzoylphosphoric acid, 4-benzoylphosphoric acid, 4-benzoylphosphoric acid, Benzo phosphoxide, 2-dibenzofo Dibenzoylphosphorus oxide, 8-dibenzoylphosphorus oxide, 8-dibenzoylphosphorus oxide, 8-dibenzoylphosphorus oxide, 9-dibenzoylphosphorus oxide, Quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-quinolyl group, 3-quinolyl group, 4-quinolyl group, Isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, A phenanthridinyl group, a 6-quinoxalinyl group, a 6-quinoxalinyl group, a 1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinyl group, Acridine group, 3-acridine group, 4-acridine group, 9-phenanthridine group, 9-phenanthridine group, An acridine group, an 1,7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, Yl group, a 1,7-phenanthroline-6-yl group, a 1,7-phenanthroline-8-yl group, a 1,7-phenanthroline- A 1,8-phenanthroline-3-yl group, a 1,8-phenanthroline-4-yl group, A 1,8-phenanthroline-6-yl group, a 1,8-phenanthroline-7-yl group, a 1,8-phenanthroline- A 1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, a 1,9-phenanthroline- A 1,9-phenanthroline-7-yl group, a 1,9-phenanthroline-8-yl group, a 1,9-phenanthroline- Phenanthroline-3-yl group, a 1,10-phenanthroline-4-yl group, a 1,10-phenanthrol-1-yl group, Yl group, a 2,9-phenanthroline-4-yl group, a 2,9-phenanthroline-1-yl group, Yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-6-yl group, 2,9- Yl group, a 2,8-phenanthroline-4-yl group, a 2,8-phenanthroline-1-yl group, A 2,8-phenanthroline-6-yl group, a 2,8-phenanthroline-7-yl group, a 2,8-phenanthroline- , 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline- A phenanthroline-6-yl group, a 2,7-phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a 2,7- , 2-phenothiazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, A 2-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxazolyl group, a 3-phenoxazoyl group, a 4-phenoxazoyl group, A thiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, Methylpyrrol-4-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol- 1-indolyl group, 4-methyl-1-indolyl group, 2- (2-methylphenyl) Indolyl group, 4-methyl-3-indolyl group, 2-tert-butyl- -tert-butyl-3-indolyl group and the like.

In addition, the R ¹ to specific examples include methyl, ethyl, a C _1-9 alkyl group of R ^14, n- propyl, n- pentyl, n- butyl, n- hexyl, n- heptyl, n- octyl, iso Propyl group, sec-butyl group, isobutyl group, tert-butyl group and the like.

Specific examples of the C _{5 -30} alkyl group of R ¹ to R ¹⁴ include a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.

Specific examples of the thio group of C _{1 -30} as the group corresponding to the above "substitution" include methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, tri (isopropyl) thio, tri (isobutyl) (3-methylphenyl) thio, (4-methylnaphthyl) thio, (2-methylthio) thio, Phenyl) thio group and the like.

Specific examples of the C _{1 -30} silyl group as the group corresponding to the above "substitution" include trimethylsilyl, triethylsilyl, tributylsilyl, tri (isopropyl) silyl, tri (isobutyl) silyl, tert- Tri (3-methylphenyl) silyl, tri (4-methylnaphthyl) silyl, triphenylsilyl, tri (Isopropyl) silyl, naphthyl (isopropyl) silyl, or phenyl or naphthyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, Biphenyl (isopropyl) silyl group and the like.

In order to improve the problem of the existing multi-ring compound, the present invention is applied to an organic electroluminescent device using a hole transporting material, a hole injecting material, a host material of a light emitting layer, an electron transporting material, A multi-ring aromatic compound exhibiting quantum efficiency and having thermal stability and electrochemical stability of molecular structure was prepared.

Hereinafter, the compounds of the multi-cyclic aromatic compounds of the present invention are represented by the compounds 31 to 168, but the present invention is not limited to these compounds.

An organic electroluminescent device according to the present invention will now be described with reference to the accompanying drawings. 1 is a schematic view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device including the multi-cyclic aromatic compound represented by the structural formula 1 can be realized in various structures.

Referring to FIG. 1, one embodiment of the present invention includes a first electrode 110; A second electrode (150); And an organic material layer 130 formed between the first electrode 110 and the second electrode 150. In the organic electroluminescent device, the organic material layer 130 includes the multi-ring aromatic compound An organic electroluminescent device is provided.

According to another embodiment of the present invention, the organic material layer 130 may be a hole transport layer.

According to another embodiment of the present invention, the organic material layer 130 may be a hole injection layer.

 According to another embodiment of the present invention, the organic material layer 130 may be an electron transport layer.

According to another embodiment of the present invention, the organic material layer 130 may be an electron injection layer.

 According to another embodiment of the present invention, the organic layer may be a light emitting layer (130).

Referring to FIG. 2, another embodiment of the present invention includes a plasma display panel including a first electrode 110; A second electrode (150); And a light emitting layer 135 between the first electrode 110 and the second electrode 150. The organic electroluminescent device includes a host and a dopant, And a multi-ring aromatic compound according to the present invention can be provided.

According to another embodiment of the present invention, a hole transport layer 133 may be additionally provided between the first electrode 110 and the light emitting layer 135.

According to another embodiment of the present invention, a hole injection layer 131 may be additionally provided between the first electrode 110 and the light emitting layer 135.

According to another embodiment of the present invention, an electron transport layer 137 may be additionally provided between the second electrode 150 and the light emitting layer 135.

According to another embodiment of the present invention, an electron injection layer 139 may be additionally provided between the second electrode 150 and the light emitting layer 135.

The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO ₂ and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.

As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO ₂ , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm. In order to increase the luminous efficiency of the organic electroluminescent device, it is preferable that at least one electrode has a light transmittance of preferably 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

The hole transporting layer or the hole injecting layer of the present invention can be used as a hole transporting material and a hole injecting material in a material commonly used as a hole transporting material in a photoconductive material and a known material used for forming a hole transporting layer or a hole injecting layer . ≪ / RTI > N, N'-di (1, 2, 3, 4, 5-tetramethyldisilazane) N, N'-di (3-methylphenyl) -4,4'-diaminobiphenyl (TPD), N, N'-diphenylbenzidine , N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N, N'N'-tetra- , Porphyrin compounds such as N, N, N'N'-tetraphenyl-4,4'-diaminobiphenyl, Copper (II) 1,10,15,20-tetraphenyl-21H, 23H- (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (p-tolyl) amine, Triarylamine derivatives such as 4'-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, Phthalocyanine derivatives such as copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.

The electron transport layer of the present invention may contain a known electron transport material such as a phosphine oxide derivative, an aluminum complex, a silole derivative, a phenanthroline derivative, a perfluorinated compound, an eight-substituted cyclooctatetraene compound and the like have.

In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

The light emitting layer of the organic electroluminescent device of the present invention may include known light emitting materials such as a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole-based compound, a phosphine oxide-based compound, an amine or a carbazole-based compound into which phosphine oxide is introduced, bis ((3,5-difluoro-4-cyanophenyl) pyridine) iridium picolinate Polyaromatic compounds such as iridium complex, tris (8-hydroxyquinoline) aluminum (Alq ₃ ), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, Benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Benzene, 1,4-bis (5-phenyl-2-oxazolyl) benzene, 2,5-bis (5-t- Liquid scintillation scintillators such as butadiene, 1,6-diphenyl-1,3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, Coumarin coloring matter, dicyanomethylenepyran coloring matter, dicyanomethylene A thiophene dye, an oxazine compound, a stilbene derivative, a spiro compound, an oxadiazole compound, and the like can be included in the present invention.

Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

Since the compound of Formula 1 according to the present invention can be formed by a vacuum deposition method, there is an advantage that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

Hereinafter, a multi-cyclic aromatic compound according to the present invention and a method of manufacturing an organic electroluminescent device including the same will be described in more detail with reference to examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.

[Example]

A multi-ring aromatic compound of the present invention was prepared, and an organic electroluminescent device was prepared using this compound. The following Preparation Examples and Examples are intended to illustrate the present invention specifically and should not be construed as limiting the invention.

Manufacturing example  1. Synthesis of Compound (15)

[Reaction Scheme 1]

 (1) Synthesis of intermediate 1

Dibromo-5,5-dimethoxybenzene (20 g, 34 mmol) was dissolved in THF (500 ml) and the temperature was lowered to -78 ° C. n-Butyllithium (1.6 M hexane solution, 106 ml) was slowly added thereto, and the mixture was stirred at -78 ° C for about 3 hours. Triethylborate (23.7 g, 162 mmol) was slowly added and stirred at room temperature for 12 hours. HCl (35%, 18 ml) was added thereto. The mixture was stirred at room temperature for 3 hours, extracted with ethyl acetate, and 9.3 g of intermediate 1 of white powder was obtained by column chromatography.

(2) Synthesis of intermediate 2

Intermediate 1 (5 g, 21.9 mmol) and 2-amino-3-bromopyridine (7.7 g, 43.8 mmol) were dissolved in THF (150 ml) and oxygen in the solution was removed through nitrogen bubbling. After potassium carbonate (18.2 g, 132 mmol) was dissolved in distilled water (50 ml), oxygen was removed, and tetraquistriphenylphosphinopalladium (1.4 g, 1.3 mmol) was added thereto, followed by reflux stirring for 24 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 3.7 g of Intermediate 2.

  (3) Synthesis of Compound (15)

[Reaction Scheme 2]

 Intermediate 2 (3.7 g, 11.5 mmol) is dissolved in a mixed solvent of acetic acid / THF (40 ml / 25 ml) and the temperature of the reaction is lowered by -10 ° C. Butyl nitrite (4.11 ml, 34.4 mmol) is slowly added and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using a developing solvent of ethyl acetate / hexane as a developing solvent to obtain 1.2 g of the compound of the formula (15).

Manufacturing example  2. Synthesis of Compound (11)

[Reaction Scheme 3]

 (1) Synthesis of intermediate 3

A solution of 2,6-diaminopyridine (10 g, 91.6 mmol) in DMF (200 ml) was cooled to -30 ° C and a solution of N-iodosuccinimide (45 g, 200 mmol) in DMF do. The reaction solution was stirred at -30 ° C for 1 hour and then at room temperature for another 1 hour. The reaction mixture was poured into cold distilled water, and the resulting precipitate was filtered, washed with distilled water and hexane, and then dried to obtain 18 g of Intermediate 3.

(2) Synthesis of intermediate 4

Intermediate 3 (3 g, 8.2 mmol) and 2-methoxyphenylboronic acid (2.5 g, 16.5 mmol) were dissolved in toluene (100 ml) and oxygen in the solution was removed through nitrogen bubbling. After potassium carbonate (6.8 g, 49.4 mmol) was dissolved in distilled water (10 ml), oxygen was removed, and tetrakistriphenylphosphinopalladium (0.53 g, 0.5 mmol) was added thereto and refluxed for 24 hours . The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as a developing solvent to obtain 1.5 g of Intermediate 4.

(3) Synthesis of Compound (11)

[Reaction Scheme 4]

 Intermediate 4 (1.5 g, 4.7 mmol) is dissolved in a mixed solvent of acetic acid / THF (15 ml / 9 ml) and the temperature of the reaction is lowered by -10 ° C. t-Butyl nitrite (1.67 ml, 14.0 mmol) was slowly added and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 0.7 g of the compound of formula (11).

Manufacturing example  3. Synthesis of Compound (1)

[Reaction Scheme 5]

 (1) Synthesis of intermediate 5

Intermediate 3 (5 g, 13.7 mmol) and 2-methoxypyridine-3-boronic acid (4.2 g, 27.4 mmol) were dissolved in THF (150 ml) and then oxygen was removed through nitrogen bubbling. After potassium carbonate (11.4 g, 82.3 mmol) was dissolved in distilled water (50 ml), oxygen was removed, and tetrakistriphenylphosphinopalladium (0.88 g, 0.82 mmol) was added thereto and refluxed for 24 hours . The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 2.7 g of Intermediate 5.

[Reaction Scheme 6]

 (2) Synthesis of Chemical Formula 1

Intermediate 5 (2.7 g, 8.35 mmol) is dissolved in a mixed solvent of acetic acid / THF (27 ml / 16 ml) and the temperature of the reaction is lowered by -10 ° C. Butyl nitrite (3.0 ml 25.1 mmol) is slowly added and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 1.1 g of the compound of the formula (1).

Production Example 4. Synthesis of Compound 31

[Reaction Scheme 7]

 (1) Synthesis of intermediate 6

Intermediate 1 (7 g, 31.0 mmol) and 2-amino-5-chloro-3-iodopyridine (15.8 g, 62.0 mmol) were dissolved in THF (210 ml) and oxygen in the solution was removed through nitrogen bubbling. Potassium carbonate (25.7 g, 186 mmol) was dissolved in distilled water (70 ml), and then oxygen was removed. Tetraquistriphenylphosphinopalladium (2.0 g, 1.9 mmol) was added thereto and refluxed for 24 hours . The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 5.1 g of Intermediate 6.

(2) Synthesis of Intermediate 7

Intermediate 6 (5.1 g, 13.0 mmol) is dissolved in a mixed solvent of acetic acid / THF (51 ml / 31 ml) and the temperature of the reaction is lowered by -10 ° C. t-Butyl nitrite (4.7 ml 39.1 mmol) was added slowly and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 1.8 g of Intermediate 7.

(3) Synthesis of Compound 31

[Reaction Scheme 8]

 Intermediate 7 (1.8 g, 5.5 mmol) and phenylboronic acid (1.67 g, 13.7 mmol) were dissolved in a mixed solvent of toluene / distilled water (60 ml / 6 ml) and oxygen was removed through nitrogen bubbling. Potassium phosphate tribasezine (7.0 g, 32.8 mmol), tris (dibenzylideneacetone) dipalladium (0.3 g, 0.33 mmol) and 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl 0.67 g, 1.64 mmol) was added to the solution, and the mixture was refluxed and stirred for 36 hours. The reaction solution was extracted with dichloromethane and then subjected to column chromatography using a dichloromethane / hexane mixed solvent as eluent to obtain 1.7 g of Compound 31.

^{NMR- 1 H (200 MHz, CDCl} 3): δ8.55 (s, 2H), 8.07 (s, 2H), 7.71-7.28 (m, 12H),

MS (FAB) m / z 412

Manufacturing example  5. Synthesis of Compound 32

[Reaction Scheme 9]

 (1) Synthesis of Intermediate 8

Intermediate 3 (36 g, 100 mmol) and 5-chloro-2-methoxyphenylboronic acid (37.3 g, 200 mmol) were dissolved in THF (1000 ml) and oxygen in the solution was removed through nitrogen bubbling.

Potassium carbonate (82.9 g, 600 mmol) was dissolved in distilled water (350 ml), and then oxygen was removed. Tetraquistriphenylphosphinopalladium (6.48 g, 6.0 mmol) was added thereto and refluxed for 24 hours . The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 20.0 g of Intermediate 8.

(2) Synthesis of intermediate 9

Intermediate 8 (20.0 g, 51.2 mmol) is dissolved in a mixed solvent of acetic acid / THF (200 ml / 120 ml) and the temperature of the reaction product is lowered by -10 ° C. Butyl nitrite (18.4 ml, 154 mmol) was slowly added and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 9.1 g of intermediate 9.

(3) Synthesis of Compound 32

[Reaction Scheme 10]

 Intermediate 9 (3.0 g, 9.1 mmol), carbazole (4.6 g, 27.4 mmol), sodium di-t-butoxide (5.27 g, 54.9 mmol), tris (dibenzylideneacetone) dipalladium ) And 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (1.5 g, 3.66 mmol) were dissolved in dried xylene (150 ml) and refluxed with stirring for 36 hours. The reaction solution was extracted with dichloromethane, and then subjected to column chromatography using a dichloromethane / hexane mixed solvent as a developing solvent to obtain 3.2 g of Compound 32.

^{NMR- 1 H (200 MHz, CDCl} 3): δ8.25-8.17 (d, 4H), 7.99 (s, 1H), 7.91-7.78 (m, 6H), 7.62-7.33 (m, 12H)

MS (FAB) m / z 589

Manufacturing example  6. Synthesis of Compound 33

[Reaction Scheme 11]

(6.56 g, 22.9 mmol) and 3- (9H-carbazol-9-yl) phenylboronic acid were dissolved in a mixed solvent of toluene and distilled water (90 ml / 10 ml) The oxygen in the solution is removed through bubbling. (0.5 g, 0.55 mmol) and tris (dibenzylideneacetone) dipalladium (0.5 g, 0.55 mmol) and 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl 1.13 g, 2.74 mmol) was added to the above solution, followed by reflux stirring for 24 hours. The reaction solution was extracted with dichloromethane, and then subjected to column chromatography using a dichloromethane / hexane mixed solvent as a developing solvent to obtain 3.9 g of Compound 33.

^{NMR- 1 H (200 MHz, CDCl} 3): δ8.28-8.19 (d, 4H), 8.00 (s, 1H), 7.91-7.22 (m, 26H)

MS (FAB) m / z 741

Manufacturing example  7. Synthesis of Compound 34

[Reaction Scheme 12]

(1) Synthesis of intermediate 10

To a solution of Intermediate 3 (25 g, 69.3 mmol) and 5-chloro-2-methoxypyridine-3-boronic acid (26.0 g, 139 mmol) in THF (750 ml) do. After dissolving potassium carbonate (57.4 g, 416 mmol) in distilled water (250 ml), oxygen was removed, tetrakis triphenylphosphinopalladium (4.49 g, 4.16 mmol) was added thereto, and the mixture was refluxed for 24 hours . The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 13.5 g of Intermediate 10.

(2) Synthesis of intermediate 11

Intermediate 10 (13.5 g, 34.4 mmol) is dissolved in a mixed solvent of acetic acid / THF (130 ml / 80 ml) and the temperature of the reaction product is lowered by -10 ° C. Butyl nitrite (12.3 ml, 103 mmol) is slowly added and stirred for 12 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 6.3 g of Intermediate 11.

(3) Synthesis of Compound 34

[Reaction Scheme 13]

 Intermediate 11 (3.0 g, 9.1 mmol), carbazole (4.6 g, 27.4 mmol), sodium di-t-butoxide (5.27 g, 54.9 mmol), tris (dibenzylideneacetone) dipalladium ) And 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (1.5 g, 3.66 mmol) were dissolved in dried xylene (150 ml) and refluxed for 24 hours. The reaction solution was extracted with dichloromethane, and then subjected to column chromatography using a dichloromethane / hexane mixed solvent as a developing solvent to obtain 3.7 g of Compound 34.

^{NMR- 1 H (200 MHz, CDCl} 3): δ 8.31 (s, 2H), 8.20-8.15 (d, 4H), 7.90-7.84 (m, 3H), 7.69-7.37 (m, 12H)

MS (FAB) m / z 589

Manufacturing example  8. Synthesis of Compound 35

[Reaction Scheme 14]

To a solution of Intermediate 11 (3.0 g, 9.1 mmol) and 3- (9H-carbazol-9-yl) phenylboronic acid (6.56 g, 22.9 mmol) in toluene / distilled water (90 ml / 10 ml) The oxygen in the solution is removed through bubbling. (0.5 g, 0.55 mmol) and tris (dibenzylideneacetone) dipalladium (0.5 g, 0.55 mmol) and 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl 1.13 g, 2.74 mmol) was added to the above solution, followed by reflux stirring for 24 hours. The reaction solution was extracted with dichloromethane, and then subjected to column chromatography using a dichloromethane / hexane mixed solvent as eluent to obtain 4.8 g of Compound 35.

^{NMR- 1 H (200 MHz, CDCl} 3): δ 8.38 (s, 2H), 8.22-8.18 (d, 4H), 7.98-7.91 (m, 3H), 7.71-7.31 (m, 20H)

MS (FAB) m / z 743

Example 1

Compound 31 synthesized in the present invention was applied as an electron transporting layer material of a green phosphorescent device to produce a green phosphorescent device. The structure of the device was ITO / DNTPD / NPB / TCTA / CBP: Ir (ppy) ₃ / compound 31 / LiF / Al.

The fabrication of the device was performed in the following manner.

The ITO substrate was cleaned with pure water and isopropyl alcohol for 30 minutes by ultrasonic wave, and the ITO substrate was surface-treated with ultraviolet rays of short wavelength and vacuum was deposited on the ITO substrate under a pressure of ¹ × 10 ^-6 torr. The green phosphorescent host material, CBP, was doped with Ir (ppy) ₃ dopant and vacuum deposited at a rate of 0.1 nm / s, and the deposition rate was CBP Was 0.1 nm / s, and Ir (ppy) ₃ was 0.005 nm / s. LiF was formed to a thickness of 1 nm at a rate of 0.01 nm / s, and Al was formed to a thickness of 100 nm at a deposition rate of 0.5 nm / sec. After the device was formed, the device was sealed using a CaO wetting agent and a glass cover glass.

Comparative Example 1

2,9-dimethyl-4,7-diphenyl-1,1, 10-phenanthroline (BCP), which is generally used as an electron transport layer instead of the compound 31, was applied as an electron transport layer material of a green phosphorescent device.

The structure of the device was ITO / DNTPD / NPB / TCTA / CBP: Ir (ppy) ₃ / BCP / LiF / Al. The fabrication process of the device was the same as in Example 1 except that BCP was used as the electron transport layer material.

Example  2

Compound 32 synthesized in the present invention was applied as a host material of a green phosphorescent device to produce an organic electroluminescent device.

The structure of the device was ITO / DNTPD / NPB / TCTA / compound 32: Ir (ppy) ₃ / BCP / LiF / Al. The manufacturing process of the device was the same as that of Comparative Example 1 except that Compound 32 was applied to the light emitting layer.

Example 3

Compound 34 synthesized in the present invention was applied as a host material of a green phosphorescent device to produce an organic electroluminescent device.

The structure of the device was ITO / DNTPD / NPB / TCTA / Compound 34: Ir (ppy) ₃ / BCP / LiF / Al. The manufacturing process of the device was the same as that of Example 2 except that Compound 34 was applied to the light emitting layer.

Example 4

Compound 33 synthesized in the present invention was applied as a host material of a blue phosphorescent device. The structure of the device was ITO / DNTPD / NPB / TCTA / Compound 33: FIrpic / BCP / LiF / Al. The manufacturing process of the device was the same as that of Comparative Example 1 except that Compound 33 and FIrpic were applied to the light emitting layer.

Example  5

Compound 35 synthesized in the present invention was applied as a host material of a blue phosphorescent device. The structure of the device was ITO / DNTPD / NPB / TCTA / Compound 35: FIrpic / BCP / LiF / Al. The manufacturing process of the device was the same as that of Example 4 except that Compound 35 was applied to the light emitting layer.

Comparative Example 2

Instead of the compound 32, mCP, which is generally used for a blue phosphorescence device, was applied as a host material of a blue phosphorescence device.

The structure of the device was ITO / DNTPD / NPB / TCTA / mCP: FIrpic / BCP / LiF / Al. The manufacturing process of the device was the same as in Example 4 except that mCP was applied to the light emitting layer.

The quantum efficiencies of Examples 1 to 5 and Comparative Examples 1 and 2 are shown in the Forrest paper (G. Gu and SR Forrest, IEEE Journal of Selected Topics in Quantum Electronics, Vol. 4, No. 1, January / February 1998, p 83 - 99). ≪ tb > < TABLE >

The driving voltage is expressed by a voltage value of luminance 1000 cd / m ² .

Referring to FIG. 3, the device using the material of the present invention exhibits a higher current density value at the same voltage, and thus it can be confirmed that the device has a lower driving voltage.

The driving voltage (V) Quantum efficiency (%) Color coordinates Example 1 5.5 17.2 0.28, 0.63 Example 2 5.5 19.0 0.28, 0.65 Example 3 5.5 18.0 0.27, 0.63 Example 4 5.5 13.9 0.15, 0.32 Example 5 5.5 13.2 0.15, 0.31 Comparative Example 1 8.0 13.5 0.27, 0.64 Comparative Example 2 7.0 6.9 0.15, 0.35

Claims (17)

A multicycyclic aromatic compound for an organic electroluminescence device represented by the following structural formula (1).
[Structural formula 1]

In formula 1,
The compound represented by Structural Formula 1 is fused in the order of a 6-membered ring structure (a), a 5-membered ring structure (b), a 6-membered ring structure (c), a 5-membered ring structure (d) Aromatic polycyclic aromatic compound,
X ¹ to X ¹⁴ may be the same or different from each other, each of X ¹ to X ¹⁴ is independently a carbon atom or a nitrogen atom, at least one of X ¹ to X ¹⁴ is a nitrogen atom,
R ¹ to R ⁶ may be the same or different from each other, and R ¹ to R ⁶ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _1-9 alkyl group, a substituted or unsubstituted C _5-30 alkyl group, a substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 A heteroaryl group,
R ¹ and R ² are taken together with the carbon atoms of the adjacent six-membered ring structure (a) to form a substituted or unsubstituted C _6-30 fused aromatic ring or a substituted or unsubstituted C _2-30 fused hetero R ³ and R ⁴ may be combined with a carbon atom of the adjacent six-membered ring structure (c) to form a substituted or unsubstituted C _6-30 bonded aromatic ring or a substituted or unsubstituted to form a conjugated heteroaromatic ring of C _2-30, and, R ⁵ and R ⁶ combine with the carbon atom of the adjacent six-membered ring structure (e) with a substituted or unsubstituted C _6-30 junction of An aromatic ring or a substituted or unsubstituted C _2-30 fused heteroaromatic ring,
R ⁷ to R ¹¹ may be the same or different from each other, and each of R ⁷ to R ¹¹ independently represents a hydrogen atom, a substituted or unsubstituted C _1-9 alkyl group, a substituted or unsubstituted C _5-30 alkyl group, A substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 heteroaryl group,
Ar ¹ to Ar ⁴ may be the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _2-30 heteroaryl group,
Y ¹ is an oxygen atom or a sulfur atom,
L and M are oxygen atoms,
The groups corresponding to " substituted " in Ar ¹ to Ar ⁴ and R ¹ to R ¹⁴ are each independently a halogen atom, a cyano group, a nitro group, a C _5-30 aryl group, a C _2-30 heteroaryl group, A C _1-9 alkyl group, a C _5-30 alkyl group, a C _1-30 thio group, or a C _1-30 silyl group. The method according to claim 1,
A multicycyclic aromatic compound for an organic electroluminescent device, wherein the formula represented by the following structural formula 2, which is the central structure of the structural formula 1, is one selected from the group consisting of the following formulas.
[Structural formula 2]

In the structural formula 2 X ¹ to X ^14, L, M, 6-membered ring structures (a), 5-membered ring structure, (b), six-membered ring structures (c), 5-membered ring structures (d) and 6 member ring structures ( e) is the same as that described in claim 1.

The compound according to claim 1, wherein R ¹ to R ⁶ may be the same or different from each other, and each of R ¹ to R ⁶ independently represents a hydrogen atom, a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, Wherein the organic compound is one selected from the group consisting of a perfluoroalkyl group and a perfluoroalkyl group. The method according to claim 1,
R ¹ to R ⁶ may be the same or different from each other, R ¹ to R ⁶ is hydrogen or

ego,
R ⁸ and R ⁹ may be the same or different from each other, and R ⁸ and R ⁹ are each independently a hydrogen atom or an alkyl group having _{1 to 9} carbon atoms. The method according to claim 1,
R ¹ to R ⁶ may be the same or different from each other, R ¹ to R ⁶ is hydrogen or

ego,
Ar ¹ and Ar ² may be the same or different and are each independently a hydrogen atom or an aryl group having _{6 to 30} carbon atoms. The method according to claim 1,
Wherein the compound represented by the five-membered ring structure (b) is furan. The method according to claim 1,
Wherein the compound represented by the five-membered ring structure (d) is furan. A first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode, the organic electroluminescent device comprising:
Wherein the organic material layer comprises the multi-ring aromatic compound according to claim 1. 9. The method of claim 8,
Wherein the organic material layer is a hole transport layer. 9. The method of claim 8,
Wherein the organic material layer is a hole injection layer. 9. The method of claim 8,
Wherein the organic material layer is an electron transporting layer. 9. The method of claim 8,
Wherein the organic material layer is an electron injection layer. 9. The method of claim 8,
Wherein the organic material layer is a light emitting layer. A first electrode; A second electrode; And a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises a host and a dopant,
The organic electroluminescent device according to claim 1, wherein the host comprises a multicyclic aromatic compound according to claim 1. 15. The method of claim 14,
And a hole transporting layer between the first electrode and the light emitting layer. 15. The method of claim 14,
And a hole injection layer between the first electrode and the light emitting layer. 15. The method of claim 14,
And an electron transport layer between the second electrode and the light emitting layer.

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