ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same. More specifically, the present invention provides an organic electroluminescent device which has a low driving voltage and is significantly improved in terms of device efficiency characteristics and lifetime.

Description

TECHNICAL FIELD

The present invention relates to an organic compound and an organic electroluminescent device including the same.

BACKGROUND

Since organic electroluminescent devices have a simpler structure than other flat panel display devices such as current liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), various advantages in a manufacturing process, high brightness and excellent viewing angle characteristics, and a fast response speed and a low driving voltage, the organic electroluminescent devices are being actively developed to be used as flat displays, such as wall-mounted TVs, or light sources, such as backlight of displays, lighting, and billboards.

In an organic electroluminescent device, generally, when a voltage is applied, holes injected from a positive electrode and electrons injected from a negative electrode are recombined to form an exciton, which is an electron-hole pair, and the energy of the exciton is transmitted to a light emitting material and converted into light.

To increase the efficiency and stability of the organic electroluminescent device, research for an organic material for a multi-layered organic electroluminescent device has been actively conducted since the low-voltage organic electroluminescent device in which the organic thin film is formed between two opposite electrodes was reported to by C. W. Tang, et al. of Eastman Kodak (C. W. Tang and S.A. Vanslyke, Applied Physics Letters, Volume 51, Pages 913, 1987).

Generally, the organic electroluminescent device has a structure which includes a negative electrode (electron injection electrode), a positive electrode (hole injection electrode), and one or more organic layers between the two electrodes. In this case, in the organic electroluminescent device, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron injection layer (EIL) may be sequentially stacked from the positive electrode, and to increase the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) may be added in front of or behind the light emitting layer.

The reason why the organic electroluminescent device is manufactured in a multi-layer thin film structure is to stabilize an interface between the electrode and the organic material and increase luminous efficiency.

In particular, in the case of organic compounds used as materials for multi-layer thin films, since there is a large difference in movement speeds of holes and electrons according to their characteristics, holes and electrons may be effectively transported to the light emitting layer only when hole transport layers and electron transport layers containing appropriate compounds are used, and thus densities of the holes and the electrons may be balanced to excellently increase luminous efficiency.

Therefore, since the characteristics of the organic compound components contained in each layer of the organic thin film layer not only greatly affects a driving voltage, luminous efficiency, luminance, and lifetime of the device, but also affect the efficiency or lifetime of a finally produced display, it is important to use specific organic materials appropriate for the multi-layer structure in the organic electroluminescent devices. Therefore, research for the components included in each layer of the organic thin film layer is actively being conducted.

DOCUMENTS OF RELATED ART

Patent Documents

• • (Patent Document 1) U.S. Pat. No. 8,207,526 B2
  • (Patent Document 2) KR10-2019-0128179 A

The present invention is directed to providing an organic electroluminescent device which includes a novel organic compound and has a low driving voltage and excellent device efficiency characteristics and lifetime characteristics.

SUMMARY

To achieve the object, the present invention may relate to a compound represented by Chemical Formula 1 below.

• • wherein,
  • n is an integer from 0 to 8,
  • m and q are the same as or different from each other and are each independently an integer from 0 to 4,
  • p is an integer from 0 to 2,
  • X is O or S,
  • L₁ to L₃ are the same as or different from each other and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,

Ar₁ and Ar₂ are selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl groups having 2 to 20 carbon atoms,

• • R₁ to R₄ are the same as or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

In addition, the present invention relates to an organic electroluminescent device including a first electrode, a second electrode facing the first electrode, and one or more organic layer interposed between the first electrode and the second electrode, wherein the one or more organic layers include a compound represented by Chemical Formula 1.

In the present invention, “hydrogen” is hydrogen, protium, deuterium, or tritium, unless otherwise specified.

In the present invention, “halogen group” indicates fluorine, chlorine, bromine, or iodine.

In the present invention, “alkyl” indicates a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like, but are not limited thereto.

In the present invention, “alkenyl” indicates a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having one or more carbon-carbon double bonds and 2 to 40 carbon atoms. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like, but are not limited thereto.

In the present invention, “alkynyl” indicates a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having one or more carbon-carbon triple bond and 2 to 40 carbon atoms. Examples thereof include ethynyl, 2-propynyl, and the like, but are not limited thereto.

In the present invention, “alkylthio” indicates the above-described alkyl group bonded through a sulfur linkage (—S—).

In the present invention, “aryl” indicates a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. In addition, forms in which two or more rings are simply pendant or condensed, specifically, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like may also be included, but the present invention is not limited thereto. The fluorenyl group may be substituted, and adjacent groups may be bonded to form a ring.

In the present invention, “heteroaryl” indicates a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, one or more carbons, preferably, 1 to 3 carbons of the ring are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls may include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, polycyclic rings such as phenoxathiinyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, “aryloxy” indicates a monovalent substituent represented by RO—, in which R indicates aryl having 6 to 60 carbon atoms. Examples of such aryloxy may include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.

In the present invention, “alkyloxy” indicates a monovalent substituent represented by R′O—, in which R′ indicates alkyl having 1 to 40 carbon atoms and may include a linear, branched, or cyclic structure. Examples of alkyloxy may include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy, but are not limited thereto.

In the present invention, “alkoxy” may be linear, branched chain, or ring chain. The number of carbon atoms of alkoxy is not especially limited, but is preferably 1 to 20. Specifically, the alkoxy may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like, but is not limited thereto.

In the present invention, “aralkyl” indicates an aryl-alkyl group in which aryl and alkyl are described above. Preferred aralkyl includes lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthalenylmethyl. Bonding to the parent moiety is made via the alkyl.

In the present invention, “arylamino group” indicates an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, “alkylamino group” indicates an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, “aralkylamino group” indicates an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, “heteroarylamino group” indicates an amine group substituted with an aryl group and heterocyclic group having 6 to 30 carbon atoms.

In the present invention, “heteroaralkyl group” indicates an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” indicates a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like, but are not limited thereto.

In the present invention, “heterocycloalkyl” indicates a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and one or more carbons, preferably, 1 to 3 carbons of the ring are substituted with a hetero atom such as N, O, S or Se. Examples of such heterocycloalkyl may include morpholine, piperazine, and the like, but are not limited thereto.

In the present invention, “alkylsilyl” indicates silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” indicates silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “condensed ring” indicates a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, “forming a ring by being bonded with adjacent groups” indicates forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by being bonded with adjacent groups.

In the present invention, examples of “aromatic hydrocarbon rings” may include a phenyl group, a naphthyl group, an anthracenyl group and the like, but are not limited thereto.

In the present invention, “aliphatic heterocycle” indicates an aliphatic ring including one or more heteroatoms.

In the present invention, “aromatic heterocycle” indicates an aromatic ring including one or more heteroatoms.

In the present invention, “substitution” indicates substituting a hydrogen atom bonded to a carbon atom of a compound with another substituent, and a location to be substituted is not limited as long as it is a location at which the hydrogen atom is substituted, that is, a location at which the substituent may be substituted, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other. The substituent may be substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, an aryl group having 5 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, but is not limited to the above examples.

Advantageous Effects

The present invention can provide the novel organic compound and can have excellent interface characteristics with adjacent layers and excellent chemical stability when used as a material for an organic electroluminescent device.

In addition, the present invention can provide the organic electroluminescent device which includes the novel organic compound and has a low driving voltage and excellent device efficiency characteristics and lifetime characteristics.

MODE FOR INVENTION

The present invention relates to a compound represented by Chemical Formula 1 below.

• • wherein,
  • n is an integer from 0 to 8,
  • m and q are the same as or different from each other and are each independently an integer from 0 to 4,
  • p is an integer from 0 to 2,
  • X is O or S,
  • L₁ to L₃ are the same as or different from each other and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
  • Ar₁ and Ar₂ are the same as or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl groups having 2 to 20 carbon atoms,
  • R₁ to R₄ are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

DETAILED DESCRIPTION

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

A novel organic compound according to the present invention may have excellent interface characteristics with adjacent layers and excellent chemical stability, and in particular, have a HOMO energy level at which hole transport is easy and thus may be used as a material for a hole transport auxiliary layer of the organic electroluminescent device with excellent hole transport characteristics to a light emitting layer.

Specifically, a compound represented by Chemical Formula 1 below is as follows:

• • wherein,
  • n is an integer from 0 to 8,
  • m and q are the same as or different from each other and are each independently an integer from 0 to 4,
  • p is an integer from 0 to 2,
  • X is O or S,
  • L₁ to L₃ are the same as or different from each other and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
  • Ar₁ and Ar₂ are the same as or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl groups having 2 to 20 carbon atoms,
  • R₁ to R₄ are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

The compound represented by Chemical Formula 1 may be compounds represented by Chemical Formulas 2 to 4 below:

• • wherein,
  • n, m, p, q, X, L₁ to L₃, Ar₁, Ar₂, and R₁ to R₄ are same as defined in Chemical Formula 1.

The compound represented by Chemical Formula 2 may be compounds represented by Chemical Formulas 5 to 7 below:

• • wherein,
  • n, m, p, q, X, L₁ to L₃, Ar₁, Ar₂, and R₁ to R₄ are same as defined in Chemical Formula 1.

The compound represented by Chemical Formula 3 may be compounds represented by Chemical Formulas 8 to 10 below:

• • wherein,
  • n, m, p, q, X, L₁ to L₃, Ar₁, Ar₂, and R₁ to R₄ are same as defined in Chemical Formula 1.

The compound represented by Chemical Formula 4 may be compounds represented by Chemical Formulas 11 to 13 below:

• • wherein,
  • n, m, p, q, X, L₁ to L₃, Ar₁, Ar₂, and R₁ to R₄ are same as defined in Chemical Formula 1.
  • L₁ to L₃ are the same as or different from each other and are each independently be selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms.
  • Ar₁ and Ar₂ are the same as or different from each other and are each independently may be selected from the group consisting of compounds represented by Chemical Formulas 14 to 17 below:

• • wherein,
  • * indicates a portion which is bonded,
  • r is an integer from 0 to 5,
  • s and v are the same as or different from each other and are each independently an integer from 0 to 7,
  • t is an integer from 0 to 4,
  • u is an integer from 0 to 6,
  • Z is C(R₁₀)(R₁₁), N(R₁₂), O or S,
  • R₅ to R₁₂ are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.
  • Ar₁ and Ar₂ are the same as or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted furan group, and a substituted or unsubstituted carbazole group.

The compound represented by Chemical Formula 1 according to the present invention is selected from the group consisting of the following compounds, but is not limited thereto:

The compound of Chemical Formula 1 of the present invention may be usefully used as a material for a hole transport auxiliary layer.

The compound of Chemical Formula 1 in one embodiment has an amine group bonded to one side and a carbazole group substituted with an aryl group bonded to the other side with respect to dibenzofuran or dibenzothiophene, and thus when used as a material for an organic electroluminescent device, can show equal or excellent characteristics in most device characteristics, such as luminous efficiency and lifetime.

The compound of Chemical Formula 1 in another embodiment has an amine group bonded to one side at any one of positions 1 to 3 of dibenzofuran or dibenzothiophene and a carbazole group substituted with an aryl group bonded to the other side at position 4 of dibenzofuran or dibenzothiophene, and thus when used as a material for an organic electroluminescent device, can show equal or excellent characteristics in most device characteristics, such as luminous efficiency and lifetime.

The carbon positions of the dibenzofuran or dibenzothiophene are as follows.

The present invention provides an organic electroluminescent device containing the compound represented by Chemical Formula 1.

The organic compound of the present invention may be usefully used as a material for a hole transport auxiliary layer.

In addition, according to the present invention, in an organic electroluminescent device in which an organic thin film layer including one or more layers including at least a light emitting layer is stacked between a positive electrode and a negative electrode, the organic thin film layer is a hole transport auxiliary layer between the first electrode and the light emitting layer.

The hole transport auxiliary layer may comprise the compound represented by Chemical Formula 1.

The hole transport auxiliary layer may adjust hole injection characteristics by reducing a difference in HOMO energy level between the hole transport layer and the light emitting layer, thereby reducing the accumulation of holes at an interface between the hole transport auxiliary layer and the light emitting layer to reduce a quenching phenomenon in which excitons extinct due to polarons at the interface. Therefore, it is possible to reduce a degradation phenomenon of the device, thereby stabilizing the device and increasing efficiency and lifetime.

The organic electroluminescent device may have a structure in which a positive electrode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, and a negative electrode are stacked, and an electron transport auxiliary layer may be added if necessary.

Hereinafter, the organic electroluminescent device of the present invention will be described as an example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which a positive electrode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, a light emitting layer (EML), and a negative electrode (electron injection electrode) are sequentially stacked and preferably, may further include a hole transport auxiliary layer between the positive electrode and the light emitting layer, and a hole transport auxiliary layer between the positive electrode and the light emitting layer, and electron transport layer (ETL) and an electron injection layer (EIL) between the negative electrode and the light emitting layer. In addition, an electron transport auxiliary layer may be further included between the negative electrode and the light emitting layer.

In a method of manufacturing an organic electroluminescent device according to the present invention, first, a positive electrode is formed by coating a surface of a substrate with a material for a positive electrode in a typical method. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used as a material for a positive electrode.

Next, a hole injection layer is formed by forming a material for a hole injection layer (HIL) on a surface of the positive electrode by vacuum thermal evaporation or spin coating in a typical method. Examples of the material for a hole injection layer may include copper phthalocyanine (CuPc), 4,4′,4″-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(3-methylphenyamino)phenoxybenzene (m-MTDAPB), 4,4′,4″-tri(N-carbazolyl)triphenylamine (TCTA) which is starburst type amines, 4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine(2-TNATA), or IDE406 available from Idemitsu.

A hole transport layer is formed by forming a material for a hole transport layer on a surface of the hole injection layer by vacuum thermal evaporation or spin coating in a typical method. As the material for a hole transport layer, a commonly used material for a hole transport layer may be used.

A hole transport auxiliary layer may be formed by forming the compound represented by Chemical Formula 1 according to the present invention on a surface of the hole transport layer by vacuum thermal evaporation or spin coating. As described above, in the hole transport auxiliary layer, the compound according to the present invention may be used as the material for a hole transport auxiliary layer, and a commonly used material for a hole transport auxiliary layer may be used to form the hole transport auxiliary layer.

A light emitting layer is formed by forming a material for a light emitting layer (EML) on a surface of the hole transport auxiliary layer by vacuum thermal evaporation or spin coating in a typical method. In this case, a sole light emitting material or light emitting host material among materials for a light emitting layer used may use Tris(8-hydroxyquinolinato)aluminium (Alq₃) or the like for green and use Alq₃, CBP(4,4′-N,N′-dicabazole-biphenyl), PVK(poly(n-vinylcabazole)), ADN(9, 10-di(naphthalene-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), E3, DSA(distyrylarylene), or a mixture of two or more thereof for blue, but the present invention is not limited thereto.

In the case of dopant which may be used together with a light emitting host among the materials for a light emitting layer, IDE102 and IDE105 available from Idemitsu company may be used, and as a phosphorescent dopant, tris(2-phenylpyridine)iridium(III)(Ir(ppy)₃), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2′]picolinate (FIrpic) (reference [Chihaya Adachi, et al., Appl. Phys. Lett., 2001, 79, 2082-2084]), platinium(II)octaethylporphyrin(PtOEP), TBE002 (by Covion company), or the like may be used.

An electron transport layer is formed by forming a material for the electron transport layer (ETL) on a surface of the light emitting layer by vacuum thermal evaporation or spin coating in a typical method. In this case, the material for an electron transport layer used is not especially limited, and Tris(8-hydroxyquinolinato)aluminium(Alq₃) may be preferably used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using the phosphorescent dopant in the light emitting layer, it is possible to prevent triplet excitons or holes from diffusing into the electron transport layer.

The formation of the hole blocking layer may be performed by vacuum thermal evaporation and spin coating of a material for a hole blocking layer in a typical method, and the material for a hole blocking layer is not especially limited, but can preferably use 8-Hydroxyquinolinolato-lithium (Liq), Bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), bathocuproine(BCP), LiF, or the like.

An electron injection layer is formed by forming a material for an electron injection layer (EIL) on a surface of the electron transport layer by vacuum thermal evaporation or spin coating in a typical method. In this case, materials such as LiF, Liq, Li₂O, BaO, NaCl, and CsF may be used as the material for an electron injection layer.

A negative electrode is formed by forming a negative electrode material on a surface of the electron injection layer by vacuum thermal deposition in a typical method.

In this case, as the negative electrode material used, lithium (Li), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag), and the like may be used. In addition, in the case of a top-emitting organic electroluminescent device, a transparent negative electrode through which light may transmit may be formed by using indium tin oxide (ITO) or indium zinc oxide (IZO).

A capping layer CPL may be formed on a surface of the negative electrode using a composition for the formation of the capping layer.

Hereinafter, a method of synthesizing the compounds will be described below as a representative example. However, the method of synthesizing the compounds of the present invention is not limited to the method exemplified below, and the compounds of the present invention may be manufactured by the methods exemplified below and methods known in the art.

Synthesis Example

1. Synthesis of SUB 1

SUB 1 may be synthesized as follows, but is not limited thereto.

Reactant 1 (89.64 mmol), Reactant 2 (94.12 mmol), t-BuONa (179.28 mmol), Pd₂(dba)₃ (1.79 mmol), sphos (3.58 mmol), and toluene were added, stirred, and refluxed in a 500 mL flask under nitrogen air flow. After the reaction was finished, an organic layer was extracted by using toluene and water. The extracted solution was treated with MgSO₄ to remove remaining moisture, concentrated under reduced pressure, purified by using a column chromatography method, and then recrystallized to obtain SUB 1.

In addition, Ar₁ and Ar₂ substituted with deuterium may be synthesized in the same manner as Reaction Formula 1. The synthesized result of SUB1 is expressed by Table 1 below.

TABLE 1
				Obtained
				amount
Item	Reactant 1	Reactant 2	SUB 1	(Yield)	[M + H]+
SUB 1-1				25.0 g (87%)	321.15
SUB 1-2				25.8 g (78%)	371.17
SUB 1-3				30.6 g (86%)	371.17
SUB 1-4				25.6 g (84%)	397.18
SUB 1-5				27.3 g (74%)	411.16
SUB 1-6				30.6 g (78%)	437.21
SUB 1-7				24.2 g (81%)	421.18
SUB 1-8				31.7 g (84%)	421.18
SUB 1-9				31.0 g (81%)	421.18
SUB 1-10				20.7 g (87%)	345.15
SUB 1-11				31.6 g (80%)	441.12
SUB 1-12				21.9 g (76%)	321.15
SUB 1-13				270.0 g (81%)	371.17
SUB 1-14				29.1 g (79%)	411.16
SUB 1-15				18.7 g (85%)	245.12
SUB 1-16				20.1 g (76%)	295.14
SUB 1-17				23.4 g (78%)	335.13
SUB 1-18				15.6 g (71%)	245.12
SUB 1-19				16.7 g (76%)	245.12
SUB 1-20				20.9 g (79%)	295.14
SUB 1-21				28.7 g (83%)	385.15
SUB 1-22				25.8 g (85%)	339.26
SUB 1-23				24.6 g (81%)	339.26
SUB 1-24				30.1 g (80%)	419.32
SUB 1-25				27.7 g (79%)	391.29
SUB 1-26				27.0 g (77%)	391.29
SUB 1-27				30.2 g (76%)	443.32
SUB 1-28				33.0 g (83%)	443.32
SUB 1-29				31.7 g (82%)	431.29
SUB 1-30				30.2 g (78%)	431.29
SUB 1-31				26.8 g (85%)	351.23
SUB 1-32				19.9 g (86%)	259.21
SUB 1-33				25.1 g (80%)	351.23
SUB 1-34				28.2 g (71%)	443.32

2. Synthesis of SUB 2

SUB 2 may be synthesized by Reaction Formula 2 below, but is not limited thereto (X may be O or S, Hal¹ may be Br, I, or C1, and Hal² may be Br).

Reactant 3 (174.1 mmol), Reactant 4 (182.8 mmol), K₂CO₃ (348.3 mmol), and Pd(PPh₃)₄ (3.48 mmol) were added to a 3000 mL flask under nitrogen air flow, and after toluene, ethanol, and water were added, stirred, and refluxed. After the reaction was finished, an organic layer was extracted by using toluene and water. The extracted solution was treated with MgSO₄ to remove remaining moisture, concentrated under reduced pressure, purified by using a column chromatography method, and then recrystallized to obtain SUB 2.

In addition, Reactants 3 and 4 substituted with deuterium may be synthesized in the same manner as Reaction Formula 2. The synthesized result of SUB 2 is expressed by Table 2 below.

TABLE 2
Item	Reactant 3	Reactant 4	SUB 2
SUB 2-1
Sub 202
SUB 2-3
SUB 2-4
SUB 2-5
SUB 2-6
SUB 2-7
SUB 2-8
SUB 2-9
SUB 2-10
SUB 2-11
SUB 2-12
SUB 2-13
SUB 2-14
SUB 2-15
SUB 2-16
SUB 2-17
SUB 2-18
SUB 2-19
SUB 2-20
SUB 2-21
SUB 2-22
SUB 2-23
SUB 2-24
SUB 2-25
SUB 2-26
SUB 2-27
SUB 2-28
SUB 2-29
SUB 2-30
SUB 2-31
SUB 2-32
SUB 2-33
SUB 2-34
SUB 2-35
SUB 2-36
	Item	Obtained amount (Yield)	[M + H]+
	SUB 2-1	69.8 g (86%)	443.11
	SUB 2-2	66.5 g (82%)	443.11
	SUB 2-3	60.7 g (76%)	459.08
	SUB 2-4	55.9 g (70%)	459.08
	SUB 2-5	62.6 g (81%)	443.11
	SUB 2-6	57.9 g (72%)	443.11
	SUB 2-7	64.7 g (81%)	459.08
	SUB 2-8	54.3 g (68%)	459.08
	SUB 2-9	58.7 g (76%)	443.11
	SUB 2-10	54.8 g (68%)	443.11
	SUB 2-11	66.3 g (83%)	459.08
	SUB 2-12	51.1 g (64%)	459.08
	SUB 2-13	35.1 g (85%)	461.22
	SUB 2-14	36.0 g (87%)	461.22
	SUB 2-15	32.5 g (76%)	477.20
	SUB 2-16	31.7 g (74%)	477.20
	SUB 2-17	34.7 g (84%)	461.22
	SUB 2-18	34.3 g (83%)	461.22
	SUB 2-19	30.4 g (71%)	477.20
	SUB 2-20	30.8 g (72%)	477.20
	SUB 2-21	35.6 g (86%)	461.22
	SUB 2-22	36.0 g (87%)	461.22
	SUB 2-23	34.2 g (80%)	477.20
	SUB 2-24	32.1 g (75%)	477.20
	SUB 2-25	30.6 g (77%)	443.11
	SUB 2-26	29.2 g (71%)	459.08
	SUB 2-27	29.8 g (75%)	443.11
	SUB 2-28	28.0 g (68%)	459.08
	SUB 2-29	29.0 g (73%)	443.11
	SUB 2-30	28.8 g (70%)	459.08
	SUB 2-31	29.4 g (71%)	461.22
	SUB 2-32	29.9 g (70%)	477.20
	SUB 2-33	31.0 g (75%)	461.22
	SUB 2-34	30.8 g (72%)	477.20
	SUB 2-35	29.4 g (71%)	461.22
	SUB 2-36	30.8 g (72%)	477.20

3. Synthesis of Product

A compound (product) may be synthesized as follows, but is not limited thereto (X may be O or S, and Hal¹ may be Br, I, or C1).

SUB 1 (16.33 mmol), SUB 2 (15.56 mmol), t-BuONa (31.11 mmol), Pd₂(dba)₃ (0.31 mmol), sphos (0.622 mmol), and toluene were added, stirred, and refluxed in a 500 mL flask under nitrogen air flow. After the reaction was finished, an organic layer was extracted by using toluene and water. The extracted solution was treated with MgSO₄ to remove remaining moisture, concentrated under reduced pressure, purified by using a column chromatography method, and then recrystallized to obtain the compound. The synthesized result of the compound (product) is expressed by Tables 3 to 20 below.

TABLE 3
				Ob-
				tained
Com-	SUB 2-1			amount	[M +
pound	SUB 2-13	SUB 1	Product	(Yield)	H]+
1				9.3 g (82%)	728.28
2				10.3 g (85%)	778.30
3				9.3 g (72%)	828.31
4				10.7 g (83%)	828.31
5				9.5 g (76%)	804.31
6				8.6 g (85%)	625.25
7				9.4 g (86%)	702.27
8				8.3 g (71%)	752.28
9				9.7 g (76%)	818.29
10				9.0 g (87%)	666.34
11				9.5 g (82%)	746.40
12				9.6 g (77%)	798.42
13				8.4 g (79%)	684.45
14				9.5 g (80%)	764.51
15				9.5 g (75%)	816.54

TABLE 4
				Ob-
				tained
Com-	SUB 2-2			amount	[M +
pound	SUB 2-14	SUB 1	Product	(Yield)	H]+
16				8.6 g (76%)	728.28
17				10.4 g (86%)	778.30
18				10.4 g (78%)	828.31
19				9.5 g (74%)	828.31
20				9.5 g (76%)	804.31
21				8.9 g (88%)	625.25
22				8.9 g (81%)	702.27
23				10.4 g (89%)	752.28
24				10.9 g (83%)	844.35
25				8.5 g (82%)	666.34
26				8.8 g (76%)	746.40
27				10.1 g (81%)	798.42
28				7.5 g (10.7 g)	684.45
29				9.2 g (77%)	764.51
30				9.4 g (74%)	816.54

TABLE 5
	SUB 2-3
Compound	SUB 2-15	SUB 1
31
32
33
34
35
36
37
38
39
40
41
42
43
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	31		8.1 g (78%)	668.23
	32		8.9 g (80%)	718.24
	33		10.0 g (85%)	758.24
	34		10.6 g (84%)	808.25
	35		10.6 g (79%)	864.23
	36		8.6 g (74%)	744.26
	37		9.4 g (76%)	794.28
	38		10.9 g (84%)	834.27
	39		11.2 g (86%)	834.27
	40		9.1 g (86%)	682.32
	41		10.0 g (84%)	762.37
	42		8.3 g (76%)	700.43
	43		9.6 g (79%)	780.49

TABLE 6
	SUB 2-4
Compound	SUB 2-16	SUB 1
44
45
46
47
48
49
50
51
52
53
54
55
56
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	44		7.9 g (76%)	668.23
	45		8.4 g (75%)	718.24
	46		9.3 g (79%)	758.24
	47		10.1 g (80%)	808.25
	48		10.0 g (74%)	864.23
	49		8.7 g (75%)	744.26
	50		9.1 g (74%)	794.28
	51		10.0 g (77%)	834.27
	52		10.3 g (79%)	834.27
	53		10.7 g (80%)	826.45
	54		8.4 g (71%)	762.37
	55		8.9 g (73%)	780.49
	56		8.7 g (72%)	780.49

TABLE 7
	SUB 2-5
Compound	SUB 2-17	SUB 1
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	57		9.8 g (86%)	729.29
	58		9.8 g (81%)	778.30
	59		9.9 g (82%)	778.30
	60		10.6 g (82%)	828.31
	61		10.8 g (84%)	828.31
	62		10.6 g (83%)	818.29
	63		8.9 g (88%)	652.25
	64		8.6 g (79%)	702.27
	65		9.1 g (78%)	752.28
	66		8.7 g (84%)	666.34
	67		9.4 g (81%)	746.40
	68		8.7 g (74%)	758.36
	69		8.5 g (80%)	684.45
	70		9.9 g (83%)	764.51
	71		9.5 g (79%)	776.48

TABLE 8
	SUB 2-6
Compound	SUB 2-18	SUB 1
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	72		8.6 g (76%)	728.28
	73		8.7 g (72%)	778.30
	74		9.1 g (75%)	778.30
	75		10.2 g (79%)	828.31
	76		10.4 g (81%)	828.31
	77		10.4 g (83%)	804.31
	78		8.1 g (80%)	652.25
	79		9.7 g (83%)	752.28
	80		11.3 g (86%)	844.35
	81		8.9 g (86%)	666.34
	82		9.1 g (78%)	746.40
	83		9.6 g (77%)	798.42
	84		8.7 g (82%)	684.45
	85		9.9 g (83%)	764.51
	86		10.2 g (80%)	816.54

TABLE 9
	SUB 2-7
Compound	SUB 2-19	SUB 1
87
88
89
90
91
92
93
94
95
96
97
98
99
			Obtained
			amount	[M +
	Compound	Product	(Yield)	H]+
	87		8.2 g (79%)	668.23
	88		8.5 g (76%)	718.24
	89		9.8 g (83%)	758.24
	90		9.1 g (72%)	808.25
	91		10.9 g (81%)	864.23
	92		9.6 g (83%)	744.26
	93		9.8 g (79%)	794.28
	94		11.2 g (86%)	834.27
	95		11.4 g (88%)	834.27
	96		10.2 g (86%)	762.37
	97		11.0 g (84%)	842.43
	98		9.2 g (76%)	780.49
	99		10.3 g (77%)	860.54

TABLE 10
	SUB 2-8
Compound	SUB 2-20	SUB 1
100
101
102
103
104
105
106
107
108
109
110
111
112
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	100		7.7 g (74%)	668.23
	101		8.6 g (77%)	718.24
	102		9.3 g (79%)	758.24
	103		10.2 g (81%)	808.25
	104		10.2 g (76%)	864.23
	105		9.3 g (80%)	744.26
	106		9.4 g (76%)	794.28
	107		9.6 g (74%)	834.27
	108		9.5 g (73%)	834.27
	109		9.7 g (72%)	826.45
	110		9.3 g (78%)	762.37
	111		10.0 g (76%)	844.57
	112		9.7 g (80%)	780.49

TABLE 11
	SUB 2-9
Compound	SUB 2-21	SUB 1
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
			Obtained
			amount
	Compound	Product	(Yield)
	113		9.9 g (87%)
	114		9.8 g (81%)
	115		10.1 g (83%)
	116		11.1 g (86%)
	117		11.0 g (85%)
	118		11.1 g (86%)
	119		10.8 g (86%)
	120		8.3 g (82%)
	121		8.6 g (79%)
	122		8.2 g (79%)
	123		10.3 g (78%)
	124		10.0 g (77%)
	125		8.4 g (79%)
	126		11.2 g (83%)
	127		10.7 g (80%)

TABLE 12
	SUB 2-10
Compound	SUB 2-22	SUB 1
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
			Obtained
			amount
	Compound	Product	(Yield)	[M + H]+
	128		9.2 g (81%)	728.28
	129		9.2 g (76%)	778.30
	130		10.2 g (79%)	828.31
	131		9.8 g (76%)	828.31
	132		10.1 g (81%)	804.31
	133		7.8 g (77%)	652.25
	134		8.1 g (74%)	702.27
	135		9.3 g (79%)	752.28
	136		10.9 g (83%)	844.35
	137		8.5 g (82%)	666.34
	138		9.1 g (78%)	746.40
	139		10.5 g (79%)	850.45
	140		7.7 g (72%)	684.45
	141		8.9 g (75%)	764.51
	142		10.4 g (77%)	868.57

TABLE 13
	SUB 2-11
Compound	SUB 2-23	SUB 1
143
144
145
146
147
148
149
150
151
152
153
154
155
			Obtained
	Compound	Product	amount	[M + H]+
	143		8.5 g (82%)	668.23
	144		8.9 g (80%)	718.24
	145		9.0 g (76%)	758.24
	146		9.3 g (74%)	808.25
	147		10.2 g (74%)	864.23
	148		9.4 g (81%)	744.26
	149		9.8 g (79%)	794.28
	150		9.9 g (76%)	834.27
	151		10.0 g (77%)	834.27
	152		8.5 g (80%)	682.32
	153		9.0 g (76%)	762.37
	154		9.0 g (83%)	700.43
	155		9.8 g (81%)	780.49

TABLE 14
	SUB 2-12
Compound	SUB 2-24	SUB 1
156
157
158
159
160
161
162
163
164
165
166
167
168
			Obtained
	Compound	Product	amount	[M + H]+
	156		7.9 g (76%)	668.23
	157		8.5 g (76%)	718.24
	158		8.7 g (74%)	758.24
	159		8.6 g (68%)	808.25
	160		9.8 g (73%)	864.23
	161		8.2 g (71%)	744.26
	162		9.1 g (74%)	794.28
	163		10.4 g (80%)	834.27
	164		9.3 g (72%)	834.27
	165		8.1 g (76%)	681.31
	166		8.5 g (72%)	761.37
	167		8.6 g (79%)	700.43
	168		9.7 g (80%)	780.49

TABLE 15
	SUB 2-25
Compound	SUB 2-31	SUB 1
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
			Obtained
	Compound	Product	amount	[M + H]+
	169		7.9 g (70%)	728.28
	170		8.1 g (67%)	778.30
	171		8.0 g (62%)	828.31
	172		8.2 g (64%)	828.31
	173		8.4 g (67%)	804.31
	174		7.0 g (72%)	625.25
	175		7.3 g (67%)	702.27
	176		7.7 g (66%)	752.28
	177		8.8 g (69%)	818.29
	178		7.7 g (74%)	666.34
	179		8.4 g (72%)	746.40
	180		8.3 g (67%)	798.42
	181		7.5 g (70%)	684.45
	182		9.0 g (76%)	764.51
	183		9.0 g (71%)	816.54

TABLE 16
	SUB 2-27
Compound	SUB 2-33	SUB 1
184
185
186
187
188
189
190
191
192
193
194
195
196
197
198
			Obtained
	Compound	Product	amount	[M + H]+
	184		8.2 g (72%)	729.29
	185		8.6 g (71%)	778.30
	186		8.1 g (67%)	778.30
	187		8.4 g (65%)	828.31
	188		8.0 g (62%)	828.31
	189		8.5 g (67%)	818.29
	190		7.7 g (76%)	652.25
	191		8.1 g (74%)	702.27
	192		8.4 g (72%)	752.28
	193		7.7 g (74%)	666.34
	194		8.7 g (75%)	746.40
	195		8.4 g (71%)	758.36
	196		7.5 g (70%)	684.45
	197		8.1 g (68%)	764.51
	198		9.2 g (76%)	776.48

TABLE 17
	SUB 2-29
Compound	SUB 2-35	SUB 1
199
200
201
202
203
204
205
206
207
208
209
210
211
212
213
			Obtained
	Compound	Product	amount	[M + H]+
	199		8.0 g (71%)	728.28
	200		9.1 g (75%)	778.30
	201		9.0 g (74%)	778.30
	202		9.0 g (70%)	828.31
	203		9.3 g (72%)	828.31
	204		8.8 g (68%)	828.31
	205		8.4 g (67%)	804.31
	206		7.2 g (71%)	652.25
	207		8.3 g (76%)	702.27
	208		7.5 g (72%)	666.34
	209		10.7 g (81%)	850.45
	210		9.7 g (74%)	838.42
	211		8.7 g (82%)	684.45
	212		11.1 g (82%)	868.57
	213		9.7 g (73%)	856.53

TABLE 18
	SUB 2-26
Compound	SUB 2-32	SUB 1
214
215
216
217
218
219
220
221
222
223
224
225
226
			Obtained
	Compound	Product	amount	[M + H]+
	214		7.3 g (70%)	668.23
	215		7.5 g (67%)	718.24
	216		7.9 g (67%)	758.24
	217		8.6 g (68%)	808.25
	218		8.2 g (61%)	864.23
	219		7.2 g (62%)	744.26
	220		8.5 g (69%)	794.28
	221		9.2 g (71%)	834.27
	222		9.1 g (70%)	834.27
	223		7.4 g (70%)	682.32
	224		8.1 g (68%)	762.37
	225		7.0 g (64%)	700.43
	226		7.4 g (61%)	780.49

TABLE 19
	SUB 2-28
Compound	SUB 2-34	SUB 1
227
228
229
230
231
232
233
234
235
236
237
238
239
			Obtained
	Compound	Product	amount	[M + H]+
	227		7.6 g (73%)	668.23
	228		8.0 g (72%)	718.24
	229		9.3 g (79%)	758.24
	230		10.1 g (80%)	808.25
	231		10.8 g (80%)	864.23
	232		8.1 g (70%)	744.26
	233		8.3 g (67%)	794.28
	234		8.0 g (62%)	834.27
	235		8.3 g (64%)	834.27
	236		7.9 g (67%)	762.37
	237		9.4 g (72%)	842.43
	238		8.1 g (67%)	780.49
	239		8.8 g (66%)	860.54

TABLE 20
	SUB 2-30
Compound	SUB 2-36	SUB 1
240
241
242
243
244
245
246
247
248
249
250
251
252
			Obtained
	Compound	Product	amount	[M + H]+
	240		7.5 g (72%)	668.23
	241		7.6 g (68%)	718.24
	242		8.6 g (73%)	758.24
	243		9.1 g (72%)	808.25
	244		8.7 g (65%)	864.23
	245		7.1 g (61%)	744.26
	246		8.4 g (68%)	794.28
	247		9.3 g (72%)	834.27
	248		8.8 g (68%)	834.27
	249		7.8 g (73%)	682.32
	250		8.3 g (70%)	762.37
	251		7.1 g (65%)	700.43
	252		7.5 g (62%)	780.49

Example 1: Manufacturing of Organic Electroluminescent Device (Green

A positive electrode was formed with ITO on a substrate on which a reflective layer was formed and surface-treated with N₂ plasma or UV-ozone. HAT-CN was deposited above the positive electrode in a thickness of 10 nm as a hole injection layer (HIL). Subsequently, a hole transport layer (HTL) was formed by depositing N4,N4,N4′,N4′-tetra([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine in a thickness of 110 nm.

A hole transport auxiliary layer was formed by forming Compound 1 of the present invention above the hole transport layer by vacuum deposition in a thickness of 40 nm, and Ir(ppy)₃[tris(2-phenylpyridine)-iridium] as a dopant was doped at about 5% while 4,4′-N,N′-dicarbazole-biphenyl(CBP) as an emitting layer (EML) was deposited above the hole transport auxiliary layer in a thickness of 35 nm.

An electron transport layer (ETL) was deposited above the light emitting layer (EML) in a thickness of 30 nm by mixing anthracene derivative and Liq at 1:1, and Liq as an electron injection layer (EIL) was deposited above the electron transport layer (ETL) in a thickness of 1 nm. Then, a mixture mixing magnesium and silver (Ag) at 1:4 was deposited in a thickness of 16 nm as a negative electrode, and N4,N4′-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (DNTPD) as a capping layer was deposited above the negative electrode in a thickness of 60 nm. An organic electroluminescent device was manufactured by bonding a sealcap containing a moisture absorbent to the capping layer using a UV curable adhesive to protect the organic electroluminescent device from O₂ or moisture in the atmosphere.

Examples 2 to 252

An organic electroluminescent device was manufactured in the same manner as Example 1 except that compounds listed in Table 21 below were used instead of Compound 1 as the hole transport auxiliary layer in Example 1.

Comparative Examples 1 to 3

An organic electroluminescent device was manufactured in the same manner as Example 1 except that Compounds A to C were used instead of Compound 1 as the hole transport auxiliary layer in Example 1.

Experimental Example 1: Device Performance Analysis

For the organic electroluminescent devices manufactured in Examples 1 to 252 and Comparative Examples 1 to 3, electroluminescent characteristics when driven at a current of 10 mA/cm² and lifetime reduced by 95% when driven at a constant current of 20 mA/cm² were measured, and a result of measurement is expressed in Table 21.

	TABLE 21
	Hole transport	Driving
	auxiliary	voltage	Efficiency	Lifetime	Color
Items	layer	(V)	Cd/A	EQE(%)	T95(hrs)	CIEx	CIEy
Example 1	Compound 1	3.86	144.2	33.7	260	0.272	0.697
Example 2	Compound 2	3.87	126.9	29.6	240	0.275	0.695
Example 3	Compound 3	3.77	131.2	30.6	220	0.274	0.696
Example 4	Compound 4	3.83	120.0	28.1	245	0.268	0.700
Example 5	Compound 5	3.78	134.0	31.8	210	0.256	0.707
Example 6	Compound 6	3.84	126.9	29.7	230	0.258	0.708
Example 7	Compound 7	3.84	146.2	34.4	230	0.258	0.708
Example 8	Compound 8	3.53	144.9	34.3	220	0.237	0.723
Example 9	Compound 9	3.55	147.1	34.8	240	0.250	0.713
Example 10	Compound 10	3.53	147.1	34.8	255	0.250	0.713
Example 11	Compound 11	3.62	141.3	33.3	285	0.259	0.707
Example 12	Compound 12	3.61	145.2	34.3	280	0.256	0.709
Example 13	Compound 13	3.65	143.9	33.8	275	0.258	0.708
Example 14	Compound 14	3.61	147.5	34.7	306	0.254	0.711
Example 15	Compound 15	3.70	130.1	31.4	327	0.236	0.719
Example 16	Compound 16	3.64	143.7	33.2	250	0.277	0.702
Example 17	Compound 17	3.61	126.4	29.1	230	0.280	0.700
Example 18	Compound 18	3.68	130.7	30.1	210	0.279	0.701
Example 19	Compound 19	3.74	119.5	27.6	235	0.273	0.705
Example 20	Compound 20	3.57	133.5	31.3	200	0.261	0.712
Example 21	Compound 21	3.58	126.4	29.2	220	0.263	0.713
Example 22	Compound 22	3.68	145.7	33.9	220	0.263	0.713
Example 23	Compound 23	3.78	144.4	33.8	210	0.242	0.728
Example 24	Compound 24	3.64	146.6	34.3	230	0.255	0.718
Example 25	Compound 25	3.55	146.6	34.3	245	0.255	0.718
Example 26	Compound 26	3.61	140.8	32.8	275	0.264	0.712
Example 27	Compound 27	3.64	144.7	33.8	270	0.261	0.714
Example 28	Compound 28	3.59	143.4	33.3	265	0.263	0.713
Example 29	Compound 29	3.62	147.0	34.2	296	0.259	0.716
Example 30	Compound 30	3.66	129.6	30.9	317	0.241	0.724
Example 31	Compound 31	3.65	157.6	36.3	235	0.265	0.698
Example 32	Compound 32	3.68	152.3	35.0	215	0.269	0.696
Example 33	Compound 33	3.54	158.6	36.8	236	0.244	0.715
Example 34	Compound 34	3.64	154.6	35.8	232	0.249	0.712
Example 35	Compound 35	3.65	158.1	36.7	250	0.244	0.715
Example 36	Compound 36	3.55	153.2	35.4	253	0.362	0.701
Example 37	Compound 37	3.58	160.1	37.1	240	0.255	0.706
Example 38	Compound 38	3.66	134.5	32.3	245	0.251	0.702
Example 39	Compound 39	3.67	137.7	32.6	253	0.252	0.704
Example 40	Compound 40	3.63	126.2	33.0	260	0.211	0.731
Example 41	Compound 41	3.69	151.1	35.8	273	0.257	0.701
Example 42	Compound 42	3.59	141.9	33.3	282	0.264	0.696
Example 43	Compound 43	3.69	137.3	32.1	300	0.262	0.698
Example 44	Compound 44	3.76	157.1	35.8	220	0.270	0.703
Example 45	Compound 45	3.71	151.8	34.5	200	0.274	0.701
Example 46	Compound 46	3.70	158.1	36.3	221	0.249	0.720
Example 47	Compound 47	3.75	154.1	35.3	217	0.254	0.717
Example 48	Compound 48	3.78	157.6	36.2	235	0.249	0.720
Example 49	Compound 49	3.79	152.7	34.9	238	0.367	0.706
Example 50	Compound 50	3.82	159.6	36.6	225	0.260	0.711
Example 51	Compound 51	3.68	134.0	31.8	230	0.256	0.707
Example 52	Compound 52	3.61	137.2	32.1	238	0.257	0.709
Example 53	Compound 53	3.60	125.7	32.5	245	0.216	0.736
Example 54	Compound 54	3.52	150.6	35.3	258	0.262	0.706
Example 55	Compound 55	3.50	141.4	32.8	267	0.269	0.701
Example 56	Compound 56	3.73	136.8	31.6	285	0.267	0.703
Example 57	Compound 57	3.73	157.6	36.3	215	0.273	0.706
Example 58	Compound 58	3.69	152.3	35.0	195	0.277	0.704
Example 59	Compound 59	3.77	158.6	36.8	216	0.252	0.723
Example 60	Compound 60	3.67	154.6	35.8	212	0.257	0.720
Example 61	Compound 61	3.78	158.1	36.7	230	0.252	0.723
Example 62	Compound 62	3.62	153.2	35.4	233	0.370	0.709
Example 63	Compound 63	3.60	160.1	37.1	220	0.263	0.714
Example 64	Compound 64	3.59	134.5	32.3	225	0.259	0.710
Example 65	Compound 65	3.69	137.7	32.6	233	0.260	0.712
Example 66	Compound 66	3.56	126.2	33.0	240	0.219	0.739
Example 67	Compound 67	3.58	151.1	35.8	253	0.265	0.709
Example 68	Compound 68	3.66	141.9	33.3	262	0.272	0.704
Example 69	Compound 69	3.56	137.3	32.1	280	0.270	0.706
Example 70	Compound 70	3.59	158.1	36.8	210	0.276	0.709
Example 71	Compound 71	3.61	152.8	35.5	190	0.280	0.707
Example 72	Compound 72	3.68	143.9	33.7	219	0.268	0.700
Example 73	Compound 73	3.71	137.7	32.3	228	0.778	0.692
Example 74	Compound 74	3.73	139.8	32.6	235	0.274	0.696
Example 75	Compound 75	3.75	136.2	32.6	228	0.239	0.719
Example 76	Compound 76	3.79	139.5	33.4	231	0.251	0.709
Example 77	Compound 77	3.76	135.7	32.6	240	0.228	0.727
Example 78	Compound 78	3.73	133.3	32.1	245	0.226	0.729
Example 79	Compound 79	3.77	131.3	31.5	233	0.238	0.720
Example 80	Compound 80	3.84	139.0	33.2	227	0.245	0.714
Example 81	Compound 81	3.70	135.7	32.6	267	0.228	0.727
Example 82	Compound 82	3.69	133.3	32.1	265	0.226	0.729
Example 83	Compound 83	3.71	137.2	32.5	270	0.245	0.717
Example 84	Compound 84	3.70	136.7	32.5	305	0.243	0.717
Example 85	Compound 85	3.75	139.2	33.0	310	0.244	0.717
Example 86	Compound 86	3.78	144.3	33.7	326	0.264	0.704
Example 87	Compound 87	3.63	126.6	30.1	248	0.209	0.725
Example 88	Compound 88	3.66	128.0	30.4	263	0.214	0.721
Example 89	Compound 89	3.65	129.2	29.5	281	0.211	0.723
Example 90	Compound 90	3.64	127.2	30.6	287	0.232	0.713
Example 91	Compound 91	3.65	144.6	34.5	250	0.238	0.709
Example 92	Compound 92	3.67	126.6	29.3	240	0.229	0.715
Example 93	Compound 93	3.68	126.3	30.8	232	0.217	0.721
Example 94	Compound 94	3.64	129.8	27.6	250	0.200	0.727
Example 95	Compound 95	3.66	123.9	26.3	232	0.197	0.728
Example 96	Compound 96	3.69	145.6	34.0	258	0.261	0.695
Example 97	Compound 97	3.64	148.6	34.7	267	0.259	0.696
Example 98	Compound 98	3.63	141.1	33.5	302	0.515	0.707
Example 99	Compound 99	3.69	144.5	33.9	314	0.259	0.695
Example 100	Compound 100	3.69	126.3	29.8	233	0.219	0.730
Example 101	Compound 101	3.72	127.7	30.1	248	0.224	0.726
Example 102	Compound 102	3.72	128.9	29.2	266	0.221	0.728
Example 103	Compound 103	3.77	126.9	30.3	272	0.242	0.718
Example 104	Compound 104	3.74	144.3	34.2	235	0.248	0.714
Example 105	Compound 105	3.66	126.3	29.0	225	0.239	0.720
Example 106	Compound 106	3.69	126.0	30.5	217	0.227	0.726
Example 107	Compound 107	3.65	129.5	27.3	235	0.210	0.732
Example 108	Compound 108	3.63	123.6	26.0	217	0.207	0.733
Example 109	Compound 109	3.76	145.3	33.7	243	0.271	0.700
Example 110	Compound 110	3.75	148.3	34.4	252	0.269	0.701
Example 111	Compound 111	3.80	140.8	33.2	287	0.525	0.712
Example 112	Compound 112	3.78	144.2	33.6	299	0.269	0.700
Example 113	Compound 113	3.65	127.0	29.6	233	0.220	0.725
Example 114	Compound 114	3.70	125.9	29.9	248	0.225	0.721
Example 115	Compound 115	3.69	134.6	29.0	266	0.222	0.723
Example 116	Compound 116	3.75	121.7	30.1	272	0.243	0.713
Example 117	Compound 117	3.70	137.6	34.0	235	0.249	0.709
Example 118	Compound 118	3.64	131.6	28.8	225	0.240	0.715
Example 119	Compound 119	3.77	133.4	30.3	217	0.228	0.721
Example 120	Compound 120	3.66	136.2	27.1	235	0.211	0.727
Example 121	Compound 121	3.71	140.0	25.8	217	0.208	0.728
Example 122	Compound 122	3.65	143.6	33.5	243	0.272	0.695
Example 123	Compound 123	3.65	137.0	34.2	252	0.270	0.696
Example 124	Compound 124	3.75	136.8	33.0	287	0.526	0.707
Example 125	Compound 125	3.58	142.4	33.4	299	0.270	0.695
Example 126	Compound 126	3.61	136.7	29.4	233	0.221	0.720
Example 127	Compound 127	3.61	135.7	29.7	248	0.226	0.716
Example 128	Compound 128	3.76	126.5	30.8	230	0.222	0.729
Example 129	Compound 129	3.77	125.4	30.2	211	0.224	0.728
Example 130	Compound 130	3.81	134.1	32.1	205	0.238	0.720
Example 131	Compound 131	3.82	121.2	29.5	222	0.238	0.715
Example 132	Compound 132	3.82	137.1	33.1	236	0.229	0.725
Example 133	Compound 133	3.80	131.1	31.7	243	0.224	0.729
Example 134	Compound 134	3.83	132.9	32.3	240	0.233	0.721
Example 135	Compound 135	3.77	135.7	32.7	235	0.245	0.713
Example 136	Compound 136	3.73	139.5	33.4	270	0.251	0.709
Example 137	Compound 137	3.68	143.1	33.5	271	0.265	0.702
Example 138	Compound 138	3.56	136.5	32.2	275	0.252	0.712
Example 139	Compound 139	3.74	136.3	32.1	242	0.263	0.703
Example 140	Compound 140	3.78	141.9	33.5	305	0.253	0.711
Example 141	Compound 141	3.73	136.2	32.6	310	0.239	0.719
Example 142	Compound 142	3.77	135.2	32.7	300	0.244	0.712
Example 143	Compound 143	3.74	131.0	31.8	235	0.257	0.705
Example 144	Compound 144	3.78	126.9	30.8	230	0.225	0.728
Example 145	Compound 145	3.81	126.8	30.7	220	0.226	0.728
Example 146	Compound 146	3.83	128.6	31.1	220	0.226	0.728
Example 147	Compound 147	3.80	139.0	33.2	285	0.245	0.714
Example 148	Compound 148	3.82	143.3	34.1	232	0.249	0.712
Example 149	Compound 149	3.79	139.5	33.4	270	0.251	0.709
Example 150	Compound 150	3.75	131.0	31.8	245	0.257	0.705
Example 151	Compound 151	3.74	136.5	32.2	225	0.252	0.712
Example 152	Compound 152	3.72	137.2	32.5	270	0.271	0.696
Example 153	Compound 153	3.70	135.5	32.3	280	0.259	0.703
Example 154	Compound 154	3.70	134.7	32.2	313	0.262	0.701
Example 155	Compound 155	3.69	128.9	31.2	321	0.242	0.713
Example 156	Compound 156	3.72	130.6	31.4	230	0.259	0.707
Example 157	Compound 157	3.74	126.5	30.4	225	0.227	0.730
Example 158	Compound 158	3.79	126.4	30.3	215	0.228	0.730
Example 159	Compound 159	3.77	128.2	30.7	215	0.228	0.730
Example 160	Compound 160	3.79	138.6	32.8	280	0.247	0.716
Example 161	Compound 161	3.78	142.9	33.7	227	0.251	0.714
Example 162	Compound 162	3.79	139.1	33.0	265	0.253	0.711
Example 163	Compound 163	3.77	130.6	31.4	240	0.259	0.707
Example 164	Compound 164	3.75	136.1	31.8	220	0.254	0.714
Example 165	Compound 165	3.70	136.8	32.1	265	0.273	0.698
Example 166	Compound 166	3.71	135.1	31.9	275	0.261	0.705
Example 167	Compound 167	3.69	134.3	31.8	308	0.264	0.703
Example 168	Compound 168	3.70	128.5	30.8	316	0.244	0.715
Example 169	Compound 169	3.93	133.7	31.7	245	0.277	0.702
Example 170	Compound 170	3.94	116.4	27.6	225	0.280	0.700
Example 171	Compound 171	3.84	120.7	28.6	205	0.279	0.701
Example 172	Compound 172	3.90	109.5	26.1	230	0.273	0.705
Example 173	Compound 173	3.85	123.5	29.8	195	0.261	0.712
Example 174	Compound 174	3.91	116.4	27.7	215	0.263	0.713
Example 175	Compound 175	3.91	135.7	32.4	215	0.263	0.713
Example 176	Compound 176	3.60	134.4	32.3	205	0.242	0.728
Example 177	Compound 177	3.62	136.6	32.8	225	0.255	0.718
Example 178	Compound 178	3.60	136.6	32.8	240	0.255	0.718
Example 179	Compound 179	3.69	130.8	31.3	270	0.264	0.712
Example 180	Compound 180	3.68	134.7	32.3	265	0.261	0.714
Example 181	Compound 181	3.72	133.4	31.8	260	0.263	0.713
Example 182	Compound 182	3.68	137.0	32.7	291	0.259	0.716
Example 183	Compound 183	3.77	119.6	29.4	312	0.241	0.724
Example 184	Compound 184	3.71	133.2	31.2	235	0.282	0.707
Example 185	Compound 185	3.68	115.9	27.1	215	0.285	0.705
Example 186	Compound 186	3.75	120.2	28.1	195	0.284	0.706
Example 187	Compound 187	3.81	109.0	25.6	220	0.278	0.710
Example 188	Compound 188	3.64	123.0	29.3	185	0.266	0.717
Example 189	Compound 189	3.65	115.9	27.2	205	0.268	0.718
Example 190	Compound 190	3.75	135.2	31.9	205	0.268	0.718
Example 191	Compound 191	3.85	133.9	31.8	195	0.247	0.733
Example 192	Compound 192	3.71	136.1	32.3	215	0.260	0.723
Example 193	Compound 193	3.62	136.1	32.3	230	0.260	0.723
Example 194	Compound 194	3.68	130.3	30.8	260	0.269	0.717
Example 195	Compound 195	3.71	134.2	31.8	255	0.266	0.719
Example 196	Compound 196	3.66	132.9	31.3	250	0.268	0.718
Example 197	Compound 197	3.69	136.5	32.2	281	0.264	0.721
Example 198	Compound 198	3.73	119.1	28.9	302	0.246	0.729
Example 199	Compound 199	3.72	147.1	34.3	220	0.270	0.703
Example 200	Compound 200	3.75	141.8	33.0	200	0.274	0.701
Example 201	Compound 201	3.61	148.1	34.8	221	0.249	0.720
Example 202	Compound 202	3.71	144.1	33.8	217	0.254	0.717
Example 203	Compound 203	3.72	147.6	34.7	235	0.249	0.720
Example 204	Compound 204	3.62	142.7	33.4	238	0.367	0.706
Example 205	Compound 205	3.65	149.6	35.1	225	0.260	0.711
Example 206	Compound 206	3.73	124.0	30.3	230	0.256	0.707
Example 207	Compound 207	3.74	127.2	30.6	238	0.257	0.709
Example 208	Compound 208	3.70	115.7	31.0	245	0.216	0.736
Example 209	Compound 209	3.76	140.6	33.8	258	0.262	0.706
Example 210	Compound 210	3.66	131.4	31.3	267	0.269	0.701
Example 211	Compound 211	3.76	126.8	30.1	285	0.267	0.703
Example 212	Compound 212	3.83	146.6	33.8	205	0.275	0.708
Example 213	Compound 213	3.78	141.3	32.5	185	0.279	0.706
Example 214	Compound 214	3.77	147.6	34.3	206	0.254	0.725
Example 215	Compound 215	3.82	143.6	33.3	202	0.259	0.722
Example 216	Compound 216	3.85	147.1	34.2	220	0.254	0.725
Example 217	Compound 217	3.86	142.2	32.9	223	0.372	0.711
Example 218	Compound 218	3.89	149.1	34.6	210	0.265	0.716
Example 219	Compound 219	3.75	123.5	29.8	215	0.261	0.712
Example 220	Compound 220	3.68	126.7	30.1	223	0.262	0.714
Example 221	Compound 221	3.67	115.2	30.5	205	0.221	0.741
Example 222	Compound 222	3.59	140.1	33.3	198	0.267	0.711
Example 223	Compound 223	3.57	130.9	30.8	252	0.274	0.706
Example 224	Compound 224	3.80	126.3	29.6	270	0.272	0.708
Example 225	Compound 225	3.80	147.1	34.3	200	0.278	0.711
Example 226	Compound 226	3.76	141.8	33.0	195	0.282	0.709
Example 227	Compound 227	3.84	148.1	34.8	201	0.257	0.728
Example 228	Compound 228	3.74	144.1	33.8	197	0.262	0.725
Example 229	Compound 229	3.85	147.6	34.7	215	0.257	0.728
Example 230	Compound 230	3.69	142.7	33.4	218	0.375	0.714
Example 231	Compound 231	3.67	149.6	35.1	205	0.268	0.719
Example 232	Compound 232	3.66	124.0	30.3	210	0.264	0.715
Example 233	Compound 233	3.76	127.2	30.6	218	0.265	0.717
Example 234	Compound 234	3.63	115.7	31.0	213	0.224	0.744
Example 235	Compound 235	3.65	140.6	33.8	225	0.270	0.714
Example 236	Compound 236	3.73	131.4	31.3	247	0.277	0.709
Example 237	Compound 237	3.63	126.8	30.1	265	0.275	0.711
Example 238	Compound 238	3.66	147.6	34.8	195	0.281	0.714
Example 239	Compound 239	3.68	142.3	33.5	175	0.285	0.712
Example 240	Compound 240	3.75	133.4	31.7	204	0.273	0.705
Example 241	Compound 241	3.78	127.2	30.3	213	0.783	0.697
Example 242	Compound 242	3.80	129.3	30.6	220	0.279	0.701
Example 243	Compound 243	3.82	125.7	30.6	213	0.244	0.724
Example 244	Compound 244	3.86	129.0	31.4	216	0.256	0.714
Example 245	Compound 245	3.83	125.2	30.6	225	0.233	0.732
Example 246	Compound 246	3.80	122.8	30.1	230	0.231	0.734
Example 247	Compound 247	3.84	120.8	29.5	218	0.243	0.725
Example 248	Compound 248	3.91	128.5	31.2	212	0.250	0.719
Example 249	Compound 249	3.77	125.2	30.6	252	0.233	0.732
Example 250	Compound 250	3.76	122.8	30.1	250	0.231	0.734
Example 251	Compound 251	3.78	126.7	30.5	255	0.250	0.722
Example 252	Compound 252	3.77	126.2	30.5	290	0.248	0.722
Comparative	[Compound A]	4.05	108.8	24.9	175	0.220	0.727
Example 1
Comparative	[Compound B]	4.01	108.7	24.1	165	0.231	0.719
Example 2
Comparative	[Compound C]	4.15	102.5	23.6	185	0.222	0.722
Example 3

Example 253: Manufacturing of Organic Electroluminescent Device (Blue)

A positive electrode was formed with ITO on a substrate on which a reflective layer was formed and surface-treated with N₂ plasma or UV-ozone. HAT-CN was deposited above the positive electrode in a thickness of 10 nm as a hole injection layer (HIL). Subsequently, a hole transport layer (HTL) was formed by depositing N4,N4,N4′,N4′-tetra([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine in a thickness of 110 nm.

A hole transport auxiliary layer was formed above the hole transport layer by forming Compound 1 by vacuum deposition in a thickness of 15 nm, and N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine as a dopant was doped at about 3 wt % while 9,10-bis(2-naphthyl)anthracene (ADN) capable of forming a blue EML as a light emitting layer (EML) was deposited above the hole transport auxiliary layer in a thickness of 25 nm.

An electron transport layer (ETL) was deposited above the light emitting layer (EML) in a thickness of 30 nm by mixing anthracene derivative and Liq at a mass ratio of 1:1, and Liq as an electron injection layer (EIL) was deposited above the electron transport layer (ETL) in a thickness of 1 nm. Then, a mixture mixing magnesium and silver (Ag) at 9:1 was deposited in a thickness of 15 nm as a negative electrode, and N4,N4′-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (DNTPD) as a capping layer was deposited above the negative electrode in a thickness of 60 nm. An organic electroluminescent device was manufactured by bonding a sealcap containing a moisture absorbent to the capping layer using a UV curable adhesive to protect the organic electroluminescent device from 02 or moisture in the atmosphere.

Examples 254 to 511

An organic electroluminescent device was manufactured in the same manner as Example 253 except that Compounds 2 to 259 listed in Table 22 below were used instead of Compound 1 as the hole transport auxiliary layer in Example 253.

Comparative Examples 4 to 6

An organic electroluminescent device was manufactured in the same manner as Example 253 except that Compounds A to C were used instead of Compound 1 as the hole transport auxiliary layer in Example 253.

Experimental Example 2: Device Performance Analysis

For the organic electroluminescent devices manufactured in Examples 253 to 511 and Comparative Examples 4 to 6, electroluminescent characteristics when driven at a current of 10 mA/cm² and lifetime reduced by 95% when driven at a constant current of 20 mA/cm² were measured, and a result of measurement is expressed in Table 22.

	TABLE 22
	Hole transport	Driving	Efficiency	Lifetime	Color
Items	auxiliary layer	voltage (V)	Cd/A	EQE(%)	T95(hrs)	CIEx	CIEy
Example 253	Compound 1	3.71	10.2	18.5	345	0.122	0.054
Example 254	Compound 2	3.72	8.9	17.9	335	0.126	0.046
Example 255	Compound 3	3.62	8.5	17.2	345	0.127	0.045
Example 256	Compound 4	3.68	8.6	17.3	375	0.127	0.045
Example 257	Compound 5	3.63	8.4	17.8	335	0.128	0.042
Example 258	Compound 6	3.69	8.7	18.0	315	0.128	0.043
Example 259	Compound 7	3.69	8.3	17.3	325	0.128	0.043
Example 260	Compound 8	3.38	9.6	19.1	365	0.126	0.046
Example 261	Compound 9	3.40	9.1	18.2	365	0.127	0.046
Example 262	Compound 10	3.38	9.6	19.3	365	0.127	0.046
Example 263	Compound 11	3.47	9.7	19.1	380	0.127	0.047
Example 264	Compound 12	3.46	8.4	17.6	390	0.128	0.043
Example 265	Compound 13	3.50	8.1	17.2	425	0.129	0.041
Example 266	Compound 14	3.46	8.4	17.4	405	0.128	0.043
Example 267	Compound 15	3.55	8.1	17.3	405	0.129	0.041
Example 268	Compound 16	3.54	10.1	18.4	330	0.132	0.057
Example 269	Compound 17	3.51	8.8	17.8	320	0.136	0.049
Example 270	Compound 18	3.58	8.4	17.1	330	0.137	0.048
Example 271	Compound 19	3.64	8.5	17.2	360	0.137	0.048
Example 272	Compound 20	3.47	8.3	17.7	320	0.138	0.045
Example 273	Compound 21	3.48	8.6	17.9	300	0.138	0.046
Example 274	Compound 22	3.58	8.2	17.2	310	0.138	0.046
Example 275	Compound 23	3.68	9.5	19.0	350	0.136	0.049
Example 276	Compound 24	3.54	9.0	18.1	350	0.137	0.049
Example 277	Compound 25	3.45	9.5	19.2	350	0.137	0.049
Example 278	Compound 26	3.51	9.6	19.0	365	0.137	0.050
Example 279	Compound 27	3.54	8.3	17.5	375	0.138	0.046
Example 280	Compound 28	3.49	8.0	17.1	410	0.139	0.044
Example 281	Compound 29	3.52	8.3	17.3	390	0.138	0.046
Example 282	Compound 30	3.56	8.0	17.2	390	0.139	0.044
Example 283	Compound 31	3.55	8.2	17.4	310	0.138	0.046
Example 284	Compound 32	3.58	8.1	17.4	320	0.139	0.044
Example 285	Compound 33	3.44	8.0	17.0	420	0.140	0.043
Example 286	Compound 34	3.54	9.0	18.1	350	0.137	0.049
Example 287	Compound 35	3.55	8.4	17.6	360	0.138	0.046
Example 288	Compound 36	3.45	8.0	17.7	300	0.140	0.042
Example 289	Compound 37	3.48	8.1	17.4	350	0.139	0.044
Example 290	Compound 38	3.56	9.1	18.6	350	0.137	0.048
Example 291	Compound 39	3.57	10.2	18.6	295	0.132	0.057
Example 292	Compound 40	3.53	9.5	18.3	340	0.134	0.053
Example 293	Compound 41	3.59	8.5	17.6	350	0.138	0.047
Example 294	Compound 42	3.49	9.1	18.3	370	0.136	0.049
Example 295	Compound 43	3.59	9.3	18.8	380	0.136	0.049
Example 296	Compound 44	3.61	7.7	16.9	300	0.139	0.047
Example 297	Compound 45	3.56	7.6	16.9	310	0.140	0.045
Example 298	Compound 46	3.55	7.5	16.5	410	0.141	0.044
Example 299	Compound 47	3.60	8.5	17.6	340	0.138	0.050
Example 300	Compound 48	3.63	7.9	17.1	350	0.139	0.047
Example 301	Compound 49	3.64	7.5	17.2	290	0.141	0.043
Example 302	Compound 50	3.67	7.6	16.9	340	0.140	0.045
Example 303	Compound 51	3.53	8.6	18.1	340	0.138	0.049
Example 304	Compound 52	3.46	9.7	18.1	285	0.133	0.058
Example 305	Compound 53	3.45	9.0	17.8	330	0.135	0.054
Example 306	Compound 54	3.37	8.0	17.1	340	0.139	0.048
Example 307	Compound 55	3.35	8.6	17.8	360	0.137	0.050
Example 308	Compound 56	3.58	8.8	18.3	370	0.137	0.050
Example 309	Compound 57	3.63	8.5	18.7	300	0.140	0.043
Example 310	Compound 58	3.59	8.1	17.9	309	0.141	0.041
Example 311	Compound 59	3.67	8.0	17.4	290	0.143	0.038
Example 312	Compound 60	3.57	8.5	17.8	315	0.138	0.046
Example 313	Compound 61	3.68	8.1	18.7	295	0.141	0.040
Example 314	Compound 62	3.52	8.3	17.2	300	0.137	0.048
Example 315	Compound 63	3.50	10.0	19.1	330	0.135	0.053
Example 316	Compound 64	3.49	8.8	17.9	300	0.137	0.048
Example 317	Compound 65	3.59	8.6	17.9	315	0.137	0.047
Example 318	Compound 66	3.46	9.4	18.1	380	0.135	0.052
Example 319	Compound 67	3.48	8.8	18.3	360	0.138	0.047
Example 320	Compound 68	3.56	8.5	18.5	340	0.140	0.043
Example 321	Compound 69	3.46	9.0	18.3	430	0.137	0.048
Example 322	Compound 70	3.49	9.1	18.4	420	0.136	0.049
Example 323	Compound 71	3.51	8.5	17.5	380	0.137	0.048
Example 324	Compound 72	3.53	8.0	18.2	280	0.141	0.044
Example 325	Compound 73	3.56	7.6	17.4	289	0.142	0.042
Example 326	Compound 74	3.58	7.5	16.9	270	0.144	0.039
Example 327	Compound 75	3.60	8.0	17.3	295	0.139	0.047
Example 328	Compound 76	3.64	7.6	18.2	275	0.142	0.041
Example 329	Compound 77	3.61	7.8	16.7	280	0.138	0.049
Example 330	Compound 78	3.58	9.5	18.6	310	0.136	0.054
Example 331	Compound 79	3.62	8.3	17.4	280	0.138	0.049
Example 332	Compound 80	3.69	8.1	17.4	295	0.138	0.048
Example 333	Compound 81	3.55	8.9	17.6	360	0.136	0.053
Example 334	Compound 82	3.54	8.3	17.8	340	0.139	0.048
Example 335	Compound 83	3.56	8.0	18.0	320	0.141	0.044
Example 336	Compound 84	3.55	8.5	17.8	410	0.138	0.049
Example 337	Compound 85	3.60	8.6	17.9	400	0.137	0.050
Example 338	Compound 86	3.63	8.0	17.0	360	0.138	0.049
Example 339	Compound 87	3.53	9.5	18.4	295	0.134	0.052
Example 340	Compound 88	3.56	10.1	18.4	340	0.132	0.057
Example 341	Compound 89	3.55	8.5	17.6	340	0.138	0.046
Example 342	Compound 90	3.54	8.2	17.1	380	0.138	0.046
Example 343	Compound 91	3.55	8.1	17.0	380	0.138	0.045
Example 344	Compound 92	3.57	9.7	17.9	330	0.134	0.055
Example 345	Compound 93	3.58	9.6	18.1	450	0.135	0.053
Example 346	Compound 94	3.54	8.4	17.8	320	0.138	0.045
Example 347	Compound 95	3.56	8.0	17.9	320	0.141	0.040
Example 348	Compound 96	3.59	8.3	17.0	390	0.139	0.043
Example 349	Compound 97	3.54	8.2	17.2	380	0.139	0.043
Example 350	Compound 98	3.53	8.0	17.1	450	0.138	0.045
Example 351	Compound 99	3.59	8.7	17.8	410	0.137	0.048
Example 352	Compound 100	3.54	9.0	17.9	255	0.135	0.053
Example 353	Compound 101	3.57	9.6	17.9	300	0.133	0.058
Example 354	Compound 102	3.57	8.0	17.1	300	0.139	0.047
Example 355	Compound 103	3.62	7.7	16.6	340	0.139	0.047
Example 356	Compound 104	3.59	7.6	16.5	340	0.139	0.046
Example 357	Compound 105	3.51	9.2	17.4	290	0.135	0.056
Example 358	Compound 106	3.54	9.1	17.6	410	0.136	0.054
Example 359	Compound 107	3.50	7.9	17.3	280	0.139	0.046
Example 360	Compound 108	3.48	7.5	17.4	280	0.142	0.041
Example 361	Compound 109	3.61	7.8	16.5	350	0.140	0.044
Example 362	Compound 110	3.60	7.7	16.7	340	0.140	0.044
Example 363	Compound 111	3.65	7.5	16.6	410	0.139	0.046
Example 364	Compound 112	3.63	8.2	17.3	370	0.138	0.049
Example 365	Compound 113	3.55	9.1	18.0	390	0.136	0.050
Example 366	Compound 114	3.60	8.0	17.9	500	0.138	0.046
Example 367	Compound 115	3.59	10.0	18.5	380	0.134	0.055
Example 368	Compound 116	3.65	8.6	17.5	300	0.137	0.048
Example 369	Compound 117	3.60	8.7	18.3	365	0.138	0.046
Example 370	Compound 118	3.54	8.8	17.8	320	0.137	0.048
Example 371	Compound 119	3.67	9.2	18.3	300	0.136	0.049
Example 372	Compound 120	3.56	9.3	18.5	360	0.136	0.050
Example 373	Compound 121	3.61	9.1	18.3	550	0.136	0.049
Example 374	Compound 122	3.55	9.2	18.0	430	0.136	0.051
Example 375	Compound 123	3.55	8.7	18.7	430	0.139	0.044
Example 376	Compound 124	3.65	9.5	18.4	380	0.136	0.049
Example 377	Compound 125	3.48	8.8	18.3	450	0.138	0.047
Example 378	Compound 126	3.51	9.7	18.4	460	0.134	0.054
Example 379	Compound 127	3.51	9.4	18.4	510	0.136	0.049
Example 380	Compound 128	3.61	8.6	17.5	340	0.138	0.052
Example 381	Compound 129	3.62	7.5	17.4	450	0.140	0.048
Example 382	Compound 130	3.66	9.5	18.0	330	0.136	0.057
Example 383	Compound 131	3.67	8.1	17.0	250	0.139	0.050
Example 384	Compound 132	3.67	8.2	17.8	315	0.140	0.048
Example 385	Compound 133	3.65	8.3	17.3	270	0.139	0.050
Example 386	Compound 134	3.68	8.7	17.8	250	0.138	0.051
Example 387	Compound 135	3.62	8.8	18.0	310	0.138	0.052
Example 387	Compound 136	3.58	8.6	17.8	500	0.138	0.051
Example 389	Compound 137	3.53	8.7	17.5	380	0.138	0.053
Example 390	Compound 138	3.41	8.2	18.2	380	0.141	0.046
Example 391	Compound 139	3.59	9.0	17.9	330	0.138	0.051
Example 392	Compound 140	3.63	8.3	17.8	400	0.140	0.049
Example 393	Compound 141	3.58	9.2	17.9	410	0.136	0.056
Example 394	Compound 142	3.62	8.9	17.9	460	0.138	0.051
Example 395	Compound 143	3.59	9.5	18.4	355	0.135	0.049
Example 396	Compound 144	3.63	9.5	18.9	385	0.136	0.046
Example 397	Compound 145	3.66	9.5	18.0	395	0.134	0.050
Example 398	Compound 146	3.68	8.5	17.4	340	0.138	0.043
Example 399	Compound 147	3.65	9.5	18.0	370	0.134	0.050
Example 400	Compound 148	3.67	9.3	18.4	390	0.135	0.047
Example 401	Compound 149	3.64	9.3	18.5	390	0.136	0.047
Example 402	Compound 150	3.60	8.5	17.4	385	0.138	0.043
Example 403	Compound 151	3.59	8.9	18.3	360	0.137	0.045
Example 404	Compound 152	3.57	9.6	18.7	410	0.135	0.048
Example 405	Compound 153	3.55	9.6	18.9	440	0.135	0.048
Example 406	Compound 154	3.55	9.5	18.7	450	0.135	0.048
Example 407	Compound 155	3.54	9.8	19.0	475	0.136	0.046
Example 408	Compound 156	3.62	9.0	17.9	315	0.136	0.050
Example 409	Compound 157	3.64	9.0	18.4	345	0.137	0.047
Example 410	Compound 158	3.69	9.0	17.5	375	0.135	0.051
Example 411	Compound 159	3.67	8.0	16.9	300	0.139	0.044
Example 412	Compound 160	3.69	9.0	17.5	330	0.135	0.051
Example 413	Compound 161	3.68	8.8	17.9	350	0.136	0.048
Example 414	Compound 162	3.69	8.8	18.0	350	0.137	0.048
Example 415	Compound 163	3.67	8.0	16.9	380	0.139	0.044
Example 416	Compound 164	3.65	8.4	17.8	320	0.138	0.046
Example 417	Compound 165	3.60	9.1	18.2	370	0.136	0.049
Example 418	Compound 166	3.61	9.1	18.4	400	0.136	0.049
Example 419	Compound 167	3.59	9.0	18.2	410	0.136	0.049
Example 420	Compound 168	3.60	9.3	18.5	435	0.137	0.047
Example 421	Compound 169	3.78	10.0	18.2	280	0.125	0.057
Example 422	Compound 170	3.79	8.7	17.6	270	0.129	0.049
Example 423	Compound 171	3.69	8.3	16.9	280	0.130	0.048
Example 424	Compound 172	3.75	8.4	17.0	310	0.130	0.048
Example 425	Compound 173	3.70	8.2	17.5	270	0.131	0.045
Example 426	Compound 174	3.76	8.5	17.7	250	0.131	0.046
Example 427	Compound 175	3.76	8.1	17.0	260	0.131	0.046
Example 428	Compound 176	3.45	9.4	18.8	300	0.129	0.049
Example 429	Compound 177	3.47	8.9	17.9	300	0.130	0.049
Example 430	Compound 178	3.45	9.4	19.0	300	0.130	0.049
Example 431	Compound 179	3.54	9.5	18.8	315	0.130	0.050
Example 432	Compound 180	3.53	8.2	17.3	325	0.131	0.046
Example 433	Compound 181	3.57	7.9	16.9	360	0.132	0.044
Example 434	Compound 182	3.53	8.2	17.1	340	0.131	0.046
Example 435	Compound 183	3.62	7.9	17.0	340	0.132	0.044
Example 436	Compound 184	3.61	9.9	18.1	265	0.135	0.060
Example 437	Compound 185	3.58	8.6	17.5	255	0.139	0.052
Example 438	Compound 186	3.65	8.2	16.8	265	0.140	0.051
Example 439	Compound 187	3.71	8.3	16.9	295	0.140	0.051
Example 440	Compound 188	3.54	8.1	17.4	255	0.141	0.048
Example 441	Compound 189	3.55	8.4	17.6	240	0.141	0.049
Example 442	Compound 190	3.65	8.0	16.9	245	0.141	0.049
Example 443	Compound 191	3.75	9.3	18.7	285	0.139	0.052
Example 444	Compound 192	3.61	8.8	17.8	285	0.140	0.052
Example 445	Compound 193	3.52	9.3	18.9	285	0.140	0.052
Example 446	Compound 194	3.58	9.4	18.7	300	0.140	0.053
Example 447	Compound 195	3.61	8.1	17.2	310	0.141	0.049
Example 448	Compound 196	3.56	7.8	16.8	345	0.142	0.047
Example 449	Compound 197	3.59	8.1	17.0	325	0.141	0.049
Example 450	Compound 198	3.63	7.8	16.9	325	0.142	0.047
Example 451	Compound 199	3.62	8.0	17.1	245	0.141	0.049
Example 452	Compound 200	3.65	7.9	17.1	255	0.142	0.047
Example 453	Compound 201	3.51	7.8	16.7	355	0.143	0.046
Example 454	Compound 202	3.61	8.8	17.8	285	0.140	0.052
Example 455	Compound 203	3.62	8.2	17.3	295	0.141	0.049
Example 456	Compound 204	3.52	7.8	17.4	245	0.143	0.045
Example 457	Compound 205	3.55	7.9	17.1	285	0.142	0.047
Example 458	Compound 206	3.63	8.9	18.3	285	0.140	0.051
Example 459	Compound 207	3.64	10.0	18.3	247	0.135	0.060
Example 460	Compound 208	3.60	9.3	18.0	275	0.137	0.056
Example 461	Compound 209	3.66	8.3	17.3	285	0.141	0.050
Example 462	Compound 210	3.56	8.9	18.0	305	0.139	0.052
Example 463	Compound 211	3.66	9.1	18.5	315	0.139	0.052
Example 464	Compound 212	3.68	7.5	16.6	285	0.142	0.050
Example 465	Compound 213	3.63	7.4	16.6	298	0.143	0.048
Example 466	Compound 214	3.62	7.3	16.2	345	0.144	0.047
Example 467	Compound 215	3.67	8.3	17.3	275	0.141	0.053
Example 468	Compound 216	3.70	7.7	16.8	285	0.142	0.050
Example 469	Compound 217	3.71	7.3	16.9	256	0.144	0.046
Example 470	Compound 218	3.74	7.4	16.6	275	0.143	0.048
Example 471	Compound 219	3.60	8.4	17.8	275	0.141	0.052
Example 472	Compound 220	3.53	9.5	17.8	257	0.136	0.061
Example 473	Compound 221	3.52	8.8	17.5	252	0.138	0.057
Example 474	Compound 222	3.44	7.8	16.8	261	0.142	0.051
Example 475	Compound 223	3.42	8.4	17.5	295	0.140	0.053
Example 476	Compound 224	3.65	8.6	18.0	305	0.140	0.053
Example 477	Compound 225	3.70	8.3	18.4	257	0.143	0.046
Example 478	Compound 226	3.66	7.9	17.6	244	0.144	0.044
Example 479	Compound 227	3.74	7.8	17.1	267	0.146	0.041
Example 480	Compound 228	3.64	8.3	17.5	250	0.141	0.049
Example 481	Compound 229	3.75	7.9	18.4	277	0.144	0.043
Example 482	Compound 230	3.59	8.1	16.9	255	0.140	0.051
Example 483	Compound 231	3.57	9.8	18.8	265	0.138	0.056
Example 484	Compound 232	3.56	8.6	17.6	245	0.140	0.051
Example 485	Compound 233	3.66	8.4	17.6	250	0.140	0.050
Example 486	Compound 234	3.53	9.2	17.8	268	0.138	0.055
Example 487	Compound 235	3.55	8.6	18.0	259	0.141	0.050
Example 488	Compound 236	3.63	8.3	18.2	275	0.143	0.046
Example 489	Compound 237	3.53	8.8	18.0	365	0.140	0.051
Example 490	Compound 238	3.56	8.9	18.1	355	0.139	0.052
Example 491	Compound 239	3.58	8.3	17.2	315	0.140	0.051
Example 492	Compound 240	3.60	7.8	17.9	270	0.144	0.047
Example 493	Compound 241	3.63	7.4	17.1	265	0.145	0.045
Example 494	Compound 242	3.65	7.3	16.6	249	0.147	0.042
Example 495	Compound 243	3.67	7.8	17.0	254	0.142	0.050
Example 496	Compound 244	3.71	7.4	17.9	272	0.145	0.044
Example 497	Compound 245	3.68	7.6	16.4	263	0.141	0.052
Example 498	Compound 246	3.65	9.3	18.3	245	0.139	0.057
Example 499	Compound 247	3.69	8.1	17.1	252	0.141	0.052
Example 500	Compound 248	3.76	7.9	17.1	256	0.141	0.051
Example 501	Compound 249	3.62	8.7	17.3	295	0.139	0.056
Example 502	Compound 250	3.61	8.1	17.5	275	0.142	0.051
Example 503	Compound 251	3.63	7.8	17.7	255	0.144	0.047
Example 504	Compound 252	3.62	8.3	17.5	345	0.141	0.052
Example 505	Compound 253	3.58	8.4	17.8	310	0.137	0.048
Example 506	Compound 254	3.69	8.7	17.6	325	0.130	0.043
Example 507	Compound 255	3.65	8.2	16.8	265	0.139	0.052
Example 508	Compound 256	3.51	7.8	16.7	330	0.142	0.047
Example 509	Compound 257	3.62	7.7	16.8	285	0.142	0.050
Example 510	Compound 258	3.63	7.9	17.1	330	0.139	0.047
Example 511	Compound 259	3.57	9.8	18.8	265	0.138	0.056
Comparative	[Compound A]	3.82	6.9	15.5	210	0.140	0.042
Example 4
Comparative	[Compound B]	3.80	7.1	15.9	225	0.140	0.043
Example 5
Comparative	[Compound C]	3.83	7.0	15.8	205	0.139	0.044
Example 6

Compounds 253 to 259 expressed in Table 22 are as follows.

According to the experimental result in Tables 21 and 22, it was confirmed that when the compounds of the present invention were used as a material for the hole transport auxiliary layer of the organic electroluminescent device, the driving voltage was low, and excellent device efficiency characteristics and long lifetime characteristics were shown as compared to Comparative Examples.

In other words, it was confirmed that the compounds in Comparative Examples are compounds not bonded to dibenzofuran or dibenzothiophene between the amine group and the carbazole group substituted with the aryl group, as shown in the experimental result of Comparative Examples in Tables 21 and 22, the driving voltage was high and the device efficiency and lifetime were low.

According to the experimental results in Tables 21 and 22, it was confirmed that when the compounds in part or whole substituted with deuterium of the present invention were used as a material for the hole transport auxiliary layer of the organic electroluminescent device, the driving voltage was low, and excellent device efficiency characteristics and long lifetime characteristics were shown as compared to Comparative Examples.

The present invention is not limited by the embodiments disclosed above in the specification, and it is apparent that various modifications may be made by those skilled in the art within the scope of the technical spirit of the present invention. In addition, even when the operational effects according to the configuration of the present invention have not been explicitly described in the description of the embodiments of the present invention, it goes without saying that the effects predictable by the corresponding configuration should also be recognized.

INDUSTRIAL APPLICABILITY

The present invention relates to an organic compound and an organic electroluminescent device including the same.

Claims

1. A compound represented by Chemical Formula 1:

2. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by Chemical Formulas 2 to 4 below:

3. The compound of claim 2, wherein the compound represented by Chemical Formula 2 is represented by Chemical Formulas 5 to 7 below:

4. The compound of claim 2, wherein the compound represented by Chemical Formula 3 is represented by Chemical Formulas 8 to 10 below:

5. The compound of claim 2, wherein the compound represented by Chemical Formula 4 is represented by Chemical Formulas 11 to 13 below:

6. The compound of claim 1, wherein L1 to L3 are the same as or different from each other and are each independently be selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms.

7. The compound of claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently be selected from the group consisting of compounds represented by Chemical Formulas 14 to 17 below:

8. The compound of claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted furan group, and a substituted or unsubstituted carbazole group.

9. An organic electroluminescent device comprising: a first electrode; a second electrode provided to face the first electrode; and one or more organic layers provided between the first electrode and the second electrode,wherein at least one of the one or more organic layers includes the compound of claim 1.

10. The organic electroluminescent device of claim 9, wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer.

11. The organic electroluminescent device of claim 9, wherein the organic layer is a hole transport auxiliary layer.