WO2016036031A1

WO2016036031A1 - Compound for organic electroluminescent device and organic electroluminescent device comprising the same

Info

Publication number: WO2016036031A1
Application number: PCT/KR2015/008687
Authority: WO
Inventors: Song Lee; Yu-Mi Chang; Suk Woon JUN; Jeong Ho Park; Ju-Sik Kang; Yong-Jun Shin; Nam-Choul Yang; Jae-Kyun Park
Original assignee: SK Chemicals Co Ltd
Current assignee: SK Chemicals Co Ltd
Priority date: 2014-09-05
Filing date: 2015-08-20
Publication date: 2016-03-10
Anticipated expiration: 2017-03-05
Also published as: KR20160029962A

Abstract

This invention povides a compound for an organic electroluminescent device and to an organic electroluminescent device including the same. The present invention may provide a compound for organic electroluminescent device which may be used as a dopant of the light emitting layer, improving colorimetric purity and light emission efficiency of the fluorescent light emitting material, and an organic electroluminescent device including the same.

Description

COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly, to a compound for an organic electroluminescent device, improving the light emission efficiency, and to an organic electroluminescent device including the same.

Organic electroluminescent (EL) devices have a simpler structure, various processing advantages, higher brightness, superior viewing angle properties, quicker response rate, and a lower driving voltage compared to other flat panel displays such as liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc., and are thus being thoroughly developed so as to be utilized as light sources of flat panel displays such as wall-mountable TVs, etc. or backlight units of the displays, illuminators, advertisement boards and so on.

Typically, when a direct-current voltage is applied to an organic EL device, holes injected from an anode and electrons injected from a cathode recombine to form electron-hole pairs, namely, excitons. While the excitons return to a stable ground state, energy corresponding thereto is transferred to a light emitting material and is thereby converted into light.

In order to increase efficiency and stability of an organic EL device, since C. W. Tang et al. of Eastman Kodak Company made an organic EL device operating at low voltage by forming a tandem organic thin film between two opposite electrodes (C. W. Tang, S. A. Vanslyke, Applied Physics Letters, vol. 51, pp. 913, 1987), extensive and intensive research into organic materials for organic EL devices having a multilayered thin-film structure has been ongoing. The efficiency and lifetime of such a tandem organic EL device are closely related to the molecular structure of a material for the thin film. For example, quantum efficiency may greatly vary depending on the structure of the material for the thin film, particularly a host material, a hole transport layer material or an electron transport layer material. When thermal stability of the material decreases, the material may be crystallized at a high temperature or a driving temperature, undesirably shortening the lifetime of the device.

Particularly, the light emitting materials can be divided into a host and a light emitting materials (dopant). The light emitting materials can be divided into the fluorescent and the phosphorescent materials in accordance with the light emitting mechanism. If the fluorescent light emitting materials are used, the fluorescent dopant materials are needed to satisfy high efficiency, high colorimetric purity and long lifetime.

Accordingly, an object of the present invention is to provide a compound for an organic EL devices which may be used as a dopant of a fluorescent light emitting layer having neutral blue light emission with high electrical stability, high efficiency, high colorimetric purity and long lifetime, and an organic electroluminescent device including the same.

In addition, an organic electroluminescent device including the compounds for an organic EL devices substituted with alkyl group and silyl group at the 4 and 9 position of the pyrene can be implemented high efficiency, high colorimetric purity and long lifetime.

In order to accomplish the above objects, an aspect of the present invention provides a compound for an organic EL device, as represented by Chemical Formula 1 below.

[Chemical Formula 1]

In Chemical Formula 1, R¹ to R⁶are identical to or different from each other, and R¹ to R⁶are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X² are identical to or different from each other, and X¹ and X² are each independently a carbon atom or a silicon atom,

m is 0 or 1, and

R⁷to R¹⁴ are identical to or different from each other, and R⁷to R¹⁴ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷to R¹⁴ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by Chemical Formula 2 below.

[Chemical Formula 2]

In Chemical Formula 2, R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

m is 0 or 1, and

R⁷to R¹⁴are identical to or different from each other, and R⁷to R¹⁴ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷to R¹⁴is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by Chemical Formula 3 below.

[Chemical Formula 3]

In Chemical Formulas 3, R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X² are identical to or different from each other, and, X¹and X² are each independently a carbon atom or a silicon atom,

n is 0 or 1,

R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are identical to or different from each other, and R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Y¹ and Y² are identical to or different from each other, and, Y¹ and Y² are each independently a oxygen atom, a sulfur atom or

, and

R¹⁷ and R¹⁸ are identical to or different from each other, and R¹⁷ and R¹⁸ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by Chemical Formula 4 below.

[Chemical Formula 4]

In Chemical Formulas 4, R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X² are identical to or different from each other, and, X¹ and X² are each independently a carbon atom or a silicon atom,

n is 0 or 1,

R⁷to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are identical to or different from each other, and R⁷to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Y¹ and Y²are identical to or different from each other, and, Y¹ and Y² are each independently a oxygen atom, a sulfur atom or

, and

R¹⁷ and R¹⁸ are identical to or different from each other, and R¹⁷ and R¹⁸are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Examples of the substituted or unsubstituted C6 to C30 aryl group may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted perylenyl group.

Examples of the substituted or unsubstituted C2 to C30 heteroaryl group may include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphpyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, or a substituted or unsubstituted phenanthrolinyl group. Preferably useful is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

According to a preferred embodiment of the present invention, the compound for an organic EL device is any one selected from among compounds represented by the following chemical formulas.

According to an embodiment of the present invention, an organic electroluminescent (EL) device including the compound for an organic EL device according to the present invention may be provided.

According to an embodiment of the present invention, an organic EL device may include a first electrode, a second electrode, and a single organic layer or a plurality of organic layers between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers may include the compound for an organic EL device according to the present invention.

According to an embodiment of the present invention, the single organic layer or the plurality of organic layers may include a light emitting layer.

According to an embodiment of the present invention, the plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include one or more selected from among an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer and a hole injection layer.

According to an embodiment of the present invention, the light emitting layer may include a host and a dopant.

The present invention provides a compound for an organic EL device which may be used as a dopant of a fluorescent light emitting layer having neutral blue light emission with high electrical stability, and improving colorimetric purity, light emission efficiency, and lifetime of fluorescent light-emitting material, and an organic electroluminescent device including the same.

In addition, the compound for an organic EL devices substituted with alkyl group and silyl group at the 4 and 9 positions of the pyrene can implement the organic EL device which have high efficiency, high colorimetric purity and long lifetime, compared with a organic EL device including a compound substituted with alkyl group and silyl group at the other positions of the pyrene.

The above and other objects, features and advantages of the present invention will be more clearly understood from the following detailed description taken in conjunction with the accompanying drawings, in which:

FIG. 1 is a cross-sectional view illustrating an organic EL device according to an embodiment of the present invention; and

FIG. 2 is a cross-sectional view illustrating an organic EL device according to another embodiment of the present invention.

The present invention may be variously modified, and may have a variety of embodiments, and is intended to illustrate specific embodiments. However, the following description does not limit the present invention to specific embodiments, and should be understood to include all variations, equivalents or substitutions within the spirit and scope of the present invention. Furthermore, in the description of the present invention, when it is determined that the detailed description of the related art would obscure the gist of the present invention, the description thereof will be omitted.

Also, in the following description, the terms “first,” “second” and the like are used to differentiate a certain component from other components, but the configuration of such components should not be construed to be limited by the terms. For example, a first component may be referred to as a second component, and a second component may be referred to as a first component, within the scope of the present invention.

Also, when any one component is mentioned to be “formed” or “stacked” on another component, it may be directly attached to the entire surface or one surface of another component, or a further component may be additionally interposed therebetween.

Unless otherwise stated, the singular expression includes a plural expression. In this application, the terms “include” and “have” are used to designate the presence of features, numbers, steps, operations, components, parts or combinations thereof described in the specification, not intending to exclude the presence or additional possibility of one or more different features, numbers, steps, operations, components, parts or combinations thereof are not excluded.

As used herein, unless otherwise defined, the term “valence bond” means a single bond, a double bond or a triple bond.

As used herein, unless otherwise defined, the term “substituted” means that at least one hydrogen on a substituent or a compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a silyl group, a C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C6 to C30 arylsilyl group, a C7 to C30 alkylarylsilyl group, a C7 to C30 arylalkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.

Further, among the halogen group, the hydroxyl group, the amino group, the C1 to C30 amine group, the silyl group, the C1 to C30 alkyl group, the C1 to C30 alkylsilyl group, the C3 to C30 cycloalkyl group, the C6 to C30 aryl group, the C1 to C20 alkoxy group, the C1 to C10 trifluoroalkyl group or the cyano group, which is substituted, two adjacent substituents may be fused to form a ring.

As used herein, unless otherwise defined, the term “hetero” means a functional group containing 1 ~ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon.

As used herein, unless otherwise defined, the term “combination thereof” means that two or more substituents are coupled with each other by a linker or two or more substituents are condensed to each other.

As used herein, unless otherwise defined, the term “hydrogen” means hydrogen, deuterium or tritium.

As used herein, unless otherwise defined, the term “alkyl group” means an aliphatic hydrocarbon group.

The alkyl group may be a “saturated alkyl group” without any double bond or triple bond.

The alkyl group may be an “unsaturated alkyl group” with at least one double bond or triple bond.

The term “alkenylene group” means a functional group having at least one carbon-carbon double bond between at least two carbon atoms, and the term “alkynylene group” means a functional group having at least one carbon-carbon triple bond between at least two carbon atoms. The alkyl group may be branched, linear or cyclic, regardless of whether it is saturated or unsaturated.

The alkyl group may be a C1 to C30 alkyl group, preferably a C1 to C20 alkyl, more preferably a C1 to C10 alkyl group, and much more preferably a C1 to C6 alkyl group.

For example, a C1 to C4 alkyl group indicates an alkyl chain containing 1 ~ 4 carbon atoms, particularly an alkyl chain which is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl.

Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an ethenyl group, a propenyl group, a butenyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.

The “amine group” includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

The term “cycloalkyl group” refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.

The term “heterocycloalkyl group” means a cycloalkyl group containing 1 ~ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heterocycloalkyl group is a fused ring, at least one ring may contain 1 ~ 4 heteroatoms.

The term “aromatic group” means a cyclic functional group where all ring atoms have p-orbitals, and these p-orbitals form conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

The term “aryl group” refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.

The term “heteroaryl group” means an aryl group containing 1 ~ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heteroalkyl group is a fused ring, at least one ring may contain 1 ~ 4 heteroatoms.

In the aryl group and the heteroaryl group, the number of ring atoms is the sum of the number of carbons and the number of non-carbon atoms.

When alkyl and aryl are used in combination as in “alkylaryl group” or “arylalkyl group,” “alkyl” and “aryl” respectively have the meanings as above.

The term “arylalkyl group” means an aryl substituted alkyl radical such as benzyl, and is incorporated in the alkyl group.

The term “alkylaryl group” means an alkyl substituted aryl radical, and is incorporated in the aryl group.

Below is a description of embodiments of the present invention with reference to the appended drawings, wherein the same or similar components are designated by the same reference numerals and the overlapping description thereof is omitted.

With reference to FIGS. 1 and 2, according to an embodiment of the present invention, an organic EL device 1 including the compound for an organic EL device according to the present invention may be provided.

According to another embodiment of the present invention, an organic EL device includes a first electrode 110, a second electrode 150, and a single organic layer or a plurality of organic layers 130 between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers 130 may include the compound for an organic EL device according to the present invention.

As such, the single organic layer or the plurality of organic layers 130 may include a light emitting layer 134.

The plurality of organic layers 130 include a light emitting layer 134, and the plurality of organic layers 130 may further include one or more selected from among an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole transport layer 136 and a hole injection layer 137.

The light emitting layer 134 may include a host and a dopant.

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

The anode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of 4 eV or more. Specific examples thereof may include Au metal or a transparent conductive material such as CuI, ITO (indium tin oxide), SnO₂ and ZnO. The thickness of the anode film is preferably set to 10 ~ 200 nm.

The cathode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of less than 4 eV. Specific examples thereof may include Na, a Na-K alloy, calcium, magnesium, lithium, a lithium alloy, indium, aluminum, a magnesium alloy, or an aluminum alloy. In addition, aluminum/AlO₂, aluminum/lithium, magnesium/silver or magnesium/indium may be used. The thickness of the cathode film is preferably set to 10 ~ 200 nm.

In order to increase light emission efficiency of the organic EL device, one or more electrodes preferably have a light transmittance of 10% or more. The sheet resistance of the electrodes is preferably hundreds of Ω/mm or less. The thickness of the electrodes falls in the range of 10 nm ~ 1 ㎛, and preferably 10 ~ 400 nm. Such electrodes may be manufactured in the form of a thin film using the above electrode material via vapor deposition such as chemical vapor deposition (CVD), physical vapor deposition (PVD) or the like, or sputtering.

When the compound for an organic EL device according to the present invention is used so as to be adapted for the purposes of the present invention, a hole transport material, a hole injection material, a light emitting layer material, a host material for a light emitting layer, an electron transport material, and an electron injection material, which are known, may be used alone in each organic layer, or may be used in selective combination with the compound for an organic EL device according to the present invention.

Examples of the hole transport material may include porphyrin compound derivatives including N,N-dicarbazolyl-3,5-benzene (mCP), poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N'N'-tetraphenyl-4,4'-diaminobiphenyl, 1,10,15,20-tetraphenyl-21H,23H-porphyrin copper(II), etc., triarylamine derivatives including polymers having an aromatic tertiary amine in the main chain or side chain thereof, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N-tri(p-tolyl)amine and 4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine, carbazole derivatives including N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives including metal-free phthalocyanine and copper phthalocyanine, starburst amine derivatives, enaminestilbene-based derivatives, aromatic tertiary amine-containing styrylamine compound derivatives, polysilane, etc.

Examples of the electron transport material may include diphenylphosphine oxide-4-(triphenylsilyl)phenyl (TSPO1), Alq₃, 2,5-diaryl sylol derivatives (PyPySPyPy), perfluorinated compounds (PF-6P), octasubstituted cyclooctatetraene compounds (COTs), etc.

In the organic EL device according to the present invention, an electron injection layer, an electron transport layer, a hole transport layer and a hole injection layer may be provided in the form of a single layer containing one or more kinds of the above compound, or may be provided in the form of a plurality of stacked layers containing different kinds of compounds.

The light emitting material may include, for example, photoluminescent fluorescent materials, fluorescent brighteners, laser dyes, organic scintillators and fluorescence analysis reagents. Specific examples thereof include carbazole-based compounds, phosphine oxide-based compounds, carbazole-based phosphine oxide compounds, polyaromatic compounds including bis((3,5-difluoro-4-cyanophenyl)pyridine)iridium picolinate (FCNIrpic), tris(8-hydroxyquinoline) aluminum (Alq₃), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds including quaterphenyl, scintillators for liquid scintillation including 1,4-bis(2-methylstyryl)benzene, 1,4-bis(4-methylstyryl)benzene, 1,4-bis(4-methyl-5-phenyl-2-oxazolyl)benzene, 1,4-bis(5-phenyl-2-oxazolyl)benzene, 2,5-bis(5-t-butyl-2-benzoxazolyl)thiophene, 1,4-diphenyl-1,3-butadiene, 1,6-diphenyl-1,3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarine dyes, dicyanomethylenepyran dyes, dicyanomethylenethiopyran dyes, polymethine dyes, oxobenzanthracene dyes, xanthene dyes, carbostyryl dyes, perylene dyes, oxazine compounds, stilbene derivatives, spiro compounds, oxadiazole compounds, etc.

Each layer of the organic EL device according to the present invention may be provided in the form of a thin film using a known process such as vacuum deposition, spin coating or casting, or may be manufactured using each layer material. The thickness of each layer is not particularly limited, but may be appropriately set depending on the material properties , and may be typically determined in the range of 2 ~ 5,000 nm.

Because the compound for an organic EL device according to the present invention may be subjected to vacuum deposition, a thin film formation process is simple and a uniform thin film which does not substantially have pin holes may be easily obtained.

A better understanding of the present invention regarding the synthesis of the compound for an organic EL device and the manufacture of the organic EL device including the same may be obtained through the following examples which are set forth to illustrate, but are not to be construed as limiting, the present invention.

[Example]

Preparation Example 1. Synthesis of Intermediate 1 (4,9- dibromo -1,2,3,6,7,8,-hexahydropyrene)

In a 1 L round-bottom three-neck flask, 20.8 g of 1,2,3,6,7,8,-hexahydropyrene, 35.6 g of NBS, 400 mL of dichloromethane(DCM) and 400 ml of acetonitrile(ACN) were placed, and stirred at room temperature for 24 hr. After completion of the reaction, precipitated solid product was obtained by using vaccum filtration, and then cleaned with methanol, thus obtaining 23.3 g of Intermediate 1 (yield 64%).

MS (ESI): [M+H]⁺ 366

Preparation Example 2. Synthesis of Intermediate 2 (4,9- diisopropyl -1,2,3,6,7,8,-hexahydropyrene)

In a 1 L round-bottom three-neck flask in a nitrogen atmosphere, 20.0 g of Intermediate 1, 2.0 g of [bis (diphenylphosphino)ferrocene]dichloropalladium(II), 165 ml of 1M isopropylmagnesiumbromide in tetrahydrofuran and 150 ml of dioxane were placed, and stirred at 90℃ for 12 hr. The reaction solution was cooled, and separated in layers by using dichloromethane and water, concentrated the separated dichloromethane layer, and subjected to column chromatography using the n-hexane. The obtained solid product was recrystallized from a solvent mixture of dichloromethane and methanol, and then cleaned with methanol, thus obtaining 4.0 g of Intermediate 2 (yield 25%).

MS (ESI): [M+H]⁺293

Preparation Example 3. Synthesis of Intermediate 3 (4,9-diisopropylpyrene)

In a 500 ml round-bottom three-neck flask in a nitrogen atmosphere, 3.2 g of Intermediate 2, 7.3 g of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) and 235 ml of toluene were placed, and stirred at 90℃ for 3 hr. The reaction solution was cooled, filtered with silica gel, and concentrated. The concentrated solution was recrystallized from dichloromethane and methanol, thus obtaining 2.3 g of Intermediate 3 (yield 78%).

MS (ESI): [M+H]⁺ 287

Preparation Example 4. Synthesis of Intermediate 4 (1,6- dibromo -4,9-diisopropylpyrene)

In a 250 ml round-bottom three-neck flask, 2.3 g of Intermediate 3, 2.9 g of NBS, 80 ml of dichloromethane(DCM) and 80 ml of methanol were placed, and stirred at room temperature for 24 hr. After completion of the reaction, precipitated solid product was obtained by using vaccum filtration, and then cleaned with methanol, thus obtaining 3.1 g of Intermediate 4 (yield 86%).

MS (ESI): [M+H]⁺ 445

Preparation Example 5. Synthesis of Intermediate 5 ( di - o - tolylamine )

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 2.0 g of o-toluidine, 2.1 g of o-bromotoluene, 0.2 g of tris(dibenzylidineacetone)dipalladium(0), 0.5 g of 15% tris(t-butyl)phosphine, 3.6 g of t-butoxy sodium and 62 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 2.2 g of Intermediate 5 (yield 90%).

MS (ESI): [M+H]⁺ 198

Preparation Example 6. Synthesis of Intermediate 6 ( N -( p - tolyl )-[1,1’-biphenyl]-2-amine)

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 1.4 g of p-toluidine, 2.1 g of 2-bromo-1,1’-biphenyl, 0.2 g of tris(dibenzylidineacetone)dipalladium(0), 0.4 g of 15% tris(t-butyl)phosphine, 2.7 g of t-butoxy sodium and 50 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 1.5 g of Intermediate 6 (yield 63%).

MS (ESI): [M+H]⁺ 260

Preparation Example 7. Synthesis of Intermediate 7 ( N -( p - tolyl )-[1,1’-biphenyl]-3-amine)

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 1.0 g of p-toluidine, 1.5 g of 3-bromo-1,1’-biphenyl, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.3 g of 15% tris(t-butyl)phosphine, 1.8 g of t-butoxy sodium and 30 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 1.0 g of Intermediate 7 (yield 62%).

MS (ESI): [M+H]⁺ 260

Preparation Example 8. Synthesis of Intermediate 8 ( N -( p -tolyl)naphthalene-1-amine)

In a 250 ml round-bottom three-neck flask in a nitrogen atmosphere, 3.2 g of p-toluidine, 4.1 g of 1-bromonaphthalene, 0.2 g of tris(dibenzylidineacetone)dipalladium(0), 0.5 g of 15% tris(t-butyl)phosphine, 3.8 g of t-butoxy sodium and 100 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 3.4 g of Intermediate 8 (yield 72%).

MMS (ESI): [M+H]⁺ 234

Preparation Example 9. Synthesis of Intermediate 9 ( di ([1.1’-biphenyl]-3-yl)amine)

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 2.0 g of 3-amino-1,1’-biphenyl, 2.0 g of 3-bromo 1,1’-biphenyl, 0.2 g of tris(dibenzylidineacetone)dipalladium(0), 0.8 g of 15% tris(t-butyl)phosphine, 2.9 g of t-butoxy sodium and 50 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 2.1 g of Intermediate 9 (yield 76%).

MS (ESI): [M+H]⁺ 322

Preparation Example 10. Synthesis of Intermediate 10 (N-(4-methylphenyl)-4-dibenzofuranamine)

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 2.0 g of 4-bromodibenzofuran, 1.3 g of p-toluidine, 0.2 g of tris(dibenzylidineacetone)dipalladium(0), 0.3 g of 15% tris(t-butyl)phosphine, 1.2 g of t-butoxy sodium and 35 ml of toluene were placed, and stirred at 60℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 1.7 g of Intermediate 10 (yield 77%).

MS (ESI): [M+H]+ 273

Example 1. Synthesis of Compound 1

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.6 g of Intermediate 4, 0.5 g of diphenylamine, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.8 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 1 (yield 74%).

¹H NMR(600MHz, CDCl₃): δ 8.27 (s, 2H), 8.04 (s, 2H), 7.84 (d, 2H), 7.20 (t, 8H), 7.10 (d, 8H), 6.94 (t, 4H), 3.72-3.70 (m, 2H), 1.24 (d, 12H)

MS (ESI): [M+H]⁺ 621

Example 2. Synthesis of Compound 2

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 4, 0.6 g of Intermediate 5, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.8 g of Compound 2 (yield 77%).

¹H NMR(600MHz, CDCl₃): δ 8.01 (s, 2H), 7.78 (s, 2H), 7.34 (d, 2H), 7.25-6.64 (m, 16H) 3.66-3.63 (m, 2H), 2.16 (s, 6H), 1.88 (s, 6H), 1.19 (d, 12H)

MS (ESI): [M+H]⁺677

Example 3. Synthesis of Compound 3

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.6 g of Intermediate 4, 0.5 g of m,m-ditolylamine, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.8 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 3 (yield 69%).

¹H NMR(600MHz, CDCl₃): δ 8.25 (s, 2H), 8.05 (s, 2H), 7.83 (d, 2H), 7.09-6.91 (m, 12H), 6.75 (s, 4H), 3.74-3.71 (m, 2H), 2.20 (s, 12H), 1.25 (d, 12H)

MS (ESI): [M+H]⁺ 677

Example 4. Synthesis of Compound 4

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 4, 0.9 g of p,p-ditolylamine, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.2 g of 15% tris(t-butyl)phosphine, 1.3 g of t-butoxy sodium and 20 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 4 (yield 61%).

¹H NMR(600MHz, CDCl₃): δ 8.20-7.78 (m, 6H), 7.26-6.75 (m, 16H), 3.75-3.65 (m, 2H), 2.36 (s, 12H), 1.24 (d, 12H)

MS (ESI): [M+H]⁺ 677

Example 5. Synthesis of Compound 5

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 4, 0.9 g of Intermediate 6, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.8 g of Compound 5 (yield 63%).

¹H NMR(600MHz, CDCl₃): δ 8.37-8.13 (m, 4H), 7.92 (d, 2H), 7.64 (d, 4H), 7.41-7.30(m, 10H), 7.19-7.07(m, 12H), 3.72-3.69 (m, 2H), 2.85 (s, 6H), 1.19 (d, 12H)

MS (ESI): [M+H]⁺801

Example 6. Synthesis of Compound 6

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 4, 0.8 g of Intermediate 7, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 6 (yield 45%).

¹H NMR(600MHz, CDCl₃): δ 8.25-8.05 (m, 4H), 7.87 (d, 2H), 7.47 (d, 4H), 7.35-7.26 (m, 10H), 7.15-7.05 (m, 12H), 3.72-3.69 (m, 2H), 2.85 (s, 6H), 1.19 (d, 12H)

MS (ESI): [M+H]⁺ 801

Example 7. Synthesis of Compound 7

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.6 g of Intermediate 4, 0.7 g of Intermediate 8, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.8 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 7 (yield 56%).

¹H NMR(600MHz, CDCl₃): δ 8.30-8.61 (m, 4H), 8.17 (d, 2H), 7.88 (d, 2H), 7.71 (d, 2H), 7.47-7.32 (m, 10H), 7.08-6.78 (m, 8H), 3.62-3.58 (m, 2H), 2.82 (s, 6H), 1.20 (d, 12H)

MS (ESI) [M+H]⁺ 749

Example 8. Synthesis of Compound 8

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.6 g of Intermediate 4, 0.9 g of Intermediate 9, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.8 g of t-butoxy sodium and 15 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.6 g of Compound 8 (yield 52%).

¹H NMR(600MHz, CDCl₃): δ 8.28 (s, 2H), 8.13 (s, 2H), 7.92 (d, 2H), 7.47-7.44 (m, 12H), 7.33 (t, 8H), 7.29-7.25 (m, 8H), 7.20 (d, 4H), 7.08 (d, 4H), 3.73-3.70 (m, 2H), 1.24 (d, 12H)

MS (ESI): [M+H]⁺925

Example 9. Synthesis of Compound 9

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 4, 0.9 g of Intermediate 10, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 18 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.7 g of Compound 9 (yield 53%).

¹H NMR(600MHz, CDCl₃): δ 8.20 (s, 3H), 7.96-7.93 (m, 4H), 7.68 (s, 2H), 7.42-7.37 (m, 4H), 7.34-7.31 (m, 3H), 7.17-7.15 (t, 2H), 7.09-7.03 (m, 6H), 6.84 (s, 4H), 3.64-3.62 (m, 2H), 2.82 (s, 6H), 1.22 (d, 12H)

MS (ESI): [M+H]⁺ 829

Comparative

Eexample

1. Synthesis of Comparative Compound 1

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of 1.6-dibromopyrene, 0.7 g of diphenylamine, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.2 g of 15% tris(t-butyl)phosphine, 1.1 g of t-butoxy sodium and 19 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated, and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.7 g of Comparative Compound 1 (yield 67%).

MS (ESI): [M+H]⁺ 537

Comparative Eexample 2

Preparation Example 11. Synthesis of Intermediate 11 (1,6-diisopropylpyrene)

In a 1L round-bottom three-neck flask in a nitrogen atmosphere, 20.0 g of 1.6-dibromopyrene, 2.4 g of [bis (diphenylphosphino)ferrocene]dichloropalladium(II), 220 ml of 1M isopropylmagnesium bromide in tetrahydrofuran, and 170 ml of dioxane were placed, and stirred at 90℃ for 12 hr. The reaction solution was cooled, and separated in layers by using dichloromethane and water, concentrated the separated dichloromethane layer, and subjected to column chromatography using the n-hexane. Obtained solid product was recrystallized from a solvent mixture dichloromethane and methanol, and then cleaned with methanol, thus obtaining 5.1 g of Intermediate 11 (yield 32%).

MS (ESI): [M+H]⁺ 287

Preparation Example 12. Synthesis of Intermediate 12 (1,6- diisopropyl -3,8-dibromopyrene)

In a 250 mL round-bottom three-neck flask, 4.0 g of Intermediate 11, 5.0 g of NBS, 140 mL of dichloromethane(DCM) and 140 ml of methanol were placed, and stirred at room temperature for 24 hr. After completion of the reaction, precipitated solid product was obtained by using vaccum filtration, and then cleaned with methanol, thus obtaining 2.5 g of Intermediate 12 (yield 40%).

MS (ESI): [M+H]⁺ 445

Comparative Eexample 2. Synthesis of Comparative Compound 2

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 12, 0.5 g of diphenylamine, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 16 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.8 g of Comparative Compound 2 (yield 82%).

MS (ESI): [M+H]⁺ 621

Comparative Eexample 3. Synthesis of Comparative Compound 3

In a 100 ml round-bottom three-neck flask in a nitrogen atmosphere, 0.7 g of Intermediate 12, 0.9 g of Intermediate 10, 0.1 g of tris(dibenzylidineacetone)dipalladium(0), 0.1 g of 15% tris(t-butyl)phosphine, 0.9 g of t-butoxy sodium and 18 ml of toluene were placed, and stirred at 80℃ for 12 hr. The reaction solution was cooled, filtered with silica gel, concentrated and then subjected to column chromatography with a solvent mixture of dichloromethane and n-hexane, thus obtaining 0.7 g of Comparative Compound 3 (yield 53%).

MS (ESI): [M+H]⁺ 829

Device Example 1. Manufacture of organic EL device including Compound 1 as a dopant

A glass substrate coated with an ITO (indium tin oxide) thin film having a thickness of 150 nm was ultrasonically washed with an isopropyl alcohol solvent, dried, placed in a plasma cleaning system so that the substrate was cleaned using oxygen plasma for 5 min, and then transferred into a vacuum deposition system.

The ITO transparent electrode thus prepared was used as an anode, and HT-1 was vacuum deposited on the ITO substrate, thus forming a hole injection layer having a thickness of 65 nm. Subsequently, HT-2 was deposited to a thickness of 30 nm, thus forming a hole transport layer, and compound 1 as a dopant, was deposited to 0.1nm/sec of deposition speed of BH-1 and 0.003nm/sec of deposition speed of compound 1, and compound 1 was doped with 3% of deposition speed rate, thus forming a light emitting layer to a thickness of 25 nm on the hole transport layer.

Thereafter, an electron transport layer was formed to a thickness of 30 nm by depositing ET-1 on the light emitting layer, and lithium fluoride layer having a thickness of 1 nm and Al layer having a thickness of 50 nm were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic EL device.

The deposition speeds of HT-1, HT-2 and ET-2 were respectively 0.1 nm/sec, the deposition speed of lithium fluoride was 0.02 nm/sec, and the deposition speed of Al was 0.2 nm/sec.

Device Example 2. Manufacture of organic EL device including Compound 2 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 2 was used instead of Compound 1.

Device Example 3. Manufacture of organic EL device including Compound 3 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 3 was used instead of Compound 1.

Device Example 4. Manufacture of organic EL device including Compound 4 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 4 was used instead of Compound 1.

Device Example 5. Manufacture of organic EL device including Compound 5 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 5 was used instead of Compound 1.

Device Example 6. Manufacture of organic EL device including Compound 6 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 6 was used instead of Compound 1.

Device Example 7. Manufacture of organic EL device including Compound 7 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 7 was used instead of Compound 1.

Device Example 8. Manufacture of organic EL device including Compound 8 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 8 was used instead of Compound 1.

Device Example 9. Manufacture of organic EL device including Compound 9 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Compound 9 was used instead of Compound 1.

Device Comparative Example 1. Manufacture of organic EL device including Comparative Compound 1 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Comparative Compound 1 was used instead of Compound 1.

Device Comparative Example 2. Manufacture of organic EL device including Comparative Compound 2 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Comparative Compound 2 was used instead of Compound 1.

Device Comparative Example 3. Manufacture of organic EL device including Comparative Compound 3 as a dopant

An organic EL device was manufactured in the same manner as in Device Example 1, with the exception that Comparative Compound 3 was used instead of Compound 1.

The chemical formulas of HT-1, HT-2, BH-1 and ET-1 used in the examples are represented below.

Evaluation of properties of organic EL device

The properties of the devices of Device Examples 1 to 9 and Comparative Device Examples 1 to 3 were evaluated at a brightness of 1000 cd/m², and the results are shown in Tables 1 and 2 below.

	Dopant material	External quantum efficiency (%)	The maximum emission wavelength (nm)	Color coordinatesCIE (x,y)
Device Ex. 1	Compound 1	3.70	459	0.14, 0.14
Device Ex. 2	Compound 2	4.20	453	0.14, 0.11
Device Ex. 3	Compound 3	4.25	463	0.14, 0.15
Device Ex. 4	Compound 4	4.16	471	0.13, 0.23
Device Ex. 5	Compound 5	3.83	467	0.14, 0.22
Device Ex. 6	Compound 6	3.97	467	0.13, 0.18
Device Ex. 7	Compound 7	3.79	465	0.13, 0.17
Device Ex. 8	Compound 8	4.44	461	0.14, 0.13
Device Ex. 9	Compound 9	4.62	459	0.14, 0.13
Comp. Device Ex. 1	Comparative compound 1	2.86	463	0.14, 0.20
Comp. Device Ex. 2	Comparative compound 2	3.42	463	0.14, 0.17
Comp. Device Ex. 3	Comparative compound 3	4.60	463	0.14, 0.15

	Dopant material	lifetime(T90)(h)
Device Ex. 1	Compound 1	10
Comp. Device Ex. 2	Comparative compound 2	8
Device Ex. 9	Compound 9	35
Comp. Device Ex. 3	Comparative compound 3	22

In the manufactured organic EL devices, while a voltage was increased from 0 V to 5 V, a quantity of light was measured using a brightness meter (Minolta CS-2000), and the measured value of the quantity of light was divided by the value of current, i.e. electron density, thus obtaining external quantum efficiency. Also, color coordinates value was measured using a brightness meter (Minolta CS-2000). In the manufactured organic EL devices, while a constant current of 50mA/cm² was applied continuously, brightness change was mesasured, and then measured the time(T90) that brightness was become 90% on the basis of 100% of initial brightness, thus obtaining lifetime(T90).

Claims

A compound for an organic electroluminescent device, represented by Chemical Formula 1 below:

[Chemical Formula 1]

wherein R¹ to R⁶are identical to or different from each other, and R¹ to R⁶are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X² are identical to or different from each other, and X¹ and X² are each independently a carbon atom or a silicon atom,

m is 0 or 1, and

R⁷ to R¹⁴ are identical to or different from each other, and R⁷ to R¹⁴ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷ to R¹⁴ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.
The compound of claim 1, which is represented by Chemical Formula 2 below:

[Chemical Formula 2]

wherein R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X²are identical to or different from each other, and X¹and X² are each independently a carbon atom or a silicon atom,

m is 0 or 1, and

R⁷ to R¹⁴ are identical to or different from each other, and R⁷ to R¹⁴ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷ to R¹⁴ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.
The compound of claim 1, which is represented by Chemical Formula 3 below:

[Chemical Formula 3]

wherein R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X² are identical to or different from each other, and, X¹ and X² are each independently a carbon atom or a silicon atom,

n is 0 or 1,

R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are identical to or different from each other, and R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Y¹ and Y² are identical to or different from each other, and, Y¹ and Y² are each independently a oxygen atom, a sulfur atom or
, and

R¹⁷ and R¹⁸ are identical to or different from each other, and R¹⁷ and R¹⁸ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
The compound of claim 3, which is represented by Chemical Formula 4 below:

[Chemical Formula 4]

wherein R¹ to R⁶ are identical to or different from each other, and R¹ to R⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or any two of R¹ to R⁶ form a substituted or unsubstituted C3 to C30 cycloalkyl group, together with a carbon atom therebetween,

X¹ and X²are identical to or different from each other, and, X¹and X² are each independently a carbon atom or a silicon atom,

n is 0 or 1,

R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are identical to or different from each other, and R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R⁷ to R⁹, R¹¹ to R¹³, R¹⁵ and R¹⁶ is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Y¹ and Y² are identical to or different from each other, and, Y¹ and Y² are each independently a oxygen atom, a sulfur atom or
, and

R¹⁷ and R¹⁸ are identical to or different from each other, and R¹⁷ and R¹⁸ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
The compound of claim 1, which is any one selected from among compounds represented by the following chemical formulas:
An organic electroluminescent device, including the compound of claim 1.
An organic electroluminescent device, comprising a first electrode, a second electrode, and a single organic layer or a plurality of organic layers between the first electrode and the second electrode, wherein one or more organic layers selected from among the single organic layer or the plurality of organic layers include the compound of claim 1.
The organic electroluminescent device of claim 7, wherein the single organic layer or the plurality of organic layers include a light emitting layer.
The organic electroluminescent device of claim 7, wherein the plurality of organic layers include a light emitting layer, and the plurality of organic layers further include one or more selected from among an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer and a hole injection layer.
The organic electroluminescent device of claim 8, wherein the light emitting layer includes a host and a dopant.