Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

Organic electroluminescent compounds and organic electroluminescent devices comprising the same. Provided is an organic electroluminescent compound represented by the following formula 1.

Description

[0001] This patent application is a divisional application of the patent application with international application number PCT / KR2018 / 005292, international filing date of May 9, 2018, and international publication number WO 2018 / 209339 A1, entered into the national phase in the People's Republic of China as application number 201880043294.2, entitled "Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same." TECHNICAL FIELD

[0002] The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. BACKGROUND

[0003] A small-molecule green organic electroluminescent device (OLED) was first developed by Tang et al. of Eastman Kodak by using a TPD / Alq3 double layer composed of a light-emitting layer and a charge transport layer in 1987. Since then, the development of OLEDs has been rapidly influenced and OLEDs have been commercialized. An OLED converts electrical energy into light by applying power to an organic light-emitting material, and generally comprises an anode, a cathode, and an organic layer between the two electrodes. In order to improve the efficiency and stability of the OLED, it has a multi-layer structure comprising a hole transport region, a light-emitting layer, an electron transport region, etc.

[0004] In the OLED, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc. are used as a compound contained in a hole transport region. However, an OLED using these materials has a problem in deteriorating quantum efficiency and service life. This is because when the OLED is driven at a high current, thermal stress occurs between the anode and the hole injection layer, and the thermal stress significantly reduces the service life of the device. In addition, since the organic material used in the hole transport region has a very high hole mobility, the hole-electron charge balance can be broken and the quantum efficiency (cd / A) can be reduced.

[0005] Korean Patent Application Publication No. 2015-0066202, published on June 16, 2015, and Japanese Patent Publication No. 3065125, published on May 12, 2000, disclose an OLED in which a fluorene-arylamines derivative compound is used as a hole transport material. However, there is still a need to develop a compound for improving the performance of an OLED. SUMMARY

[0006] TECHNICAL PROBLEM

[0007] An object of the present disclosure is to provide an organic electroluminescent compound which can be effectively used for producing an organic electroluminescent device having low driving voltage, high luminous efficiency, and / or long lifespan characteristics.

[0008] Solution to the problem

[0009] The inventors found that, by including a specific compound having a structure in which a fluorene-based amine is bonded to the 3-position of benzofluorene in a hole transport region, an organic electroluminescent device can exhibit low driving voltage, high luminous efficiency, and / or long lifespan characteristics. Specifically, the above object can be achieved by an organic electroluminescent compound represented by the following Formula 1:

[0010]

[0011] wherein

[0012] Ar1represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;

[0013] R1and R2each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to one or more adjacent substituents to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered aliphatic ring or aromatic ring, or a combination thereof;

[0014] R3to R7each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aromatic group (C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano group, a nitro group, or a hydroxyl group;

[0015] R 11 to R 17each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered aliphatic ring or aromatic ring, or a combination thereof; and

[0016] a and e each independently represent an integer of 1 to 4, b and c each independently represent an integer of 1 to 3, and d represents an integer of 1 or 2, where if each of a to e is an integer of 2 or more, each of R3to R7may be the same or different.

[0017] Advantages of the Invention

[0018] By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device with low driving voltage, high luminous efficiency, and / or long lifespan characteristics can be produced. BRIEF DESCRIPTION OF DRAWINGS

[0019] Figure 1 is a representative formula of the organic electroluminescent compound of the present disclosure. DETAILED DESCRIPTION

[0020] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure, and is not meant in any way to restrict the scope of the present disclosure.

[0021] The organic electroluminescent device of the present disclosure includes a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode. One of the first electrode and the second electrode can be an anode, and the other can be a cathode.

[0022] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device, and can be included in any material layer constituting the organic electroluminescent device, as necessary.

[0023] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device, and can include at least one compound. The organic electroluminescent material can be included in any layer constituting the organic electroluminescent device, as necessary. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emission auxiliary material, an electron blocking material, an emission material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0024] The term "hole transport region" in the present disclosure means a region in which holes move between the first electrode and the light-emitting layer, and can include, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer can each be a single layer or a multi-layer in which two or more layers are stacked. According to one embodiment of the present disclosure, the hole transport region can include at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0025] The hole transport layer can be disposed between the anode (or the hole injection layer) and the light-emitting layer, so that holes transferred from the anode can move smoothly to the light-emitting layer, and electrons transferred from the cathode can be blocked to confine the electrons within the light-emitting layer. The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or the hole injection layer) and the light-emitting layer, and can effectively facilitate or block the hole transport rate (or the hole injection rate), thereby enabling control of the charge balance. Further, the electron blocking layer can be disposed between the hole transport layer (or the hole injection layer) and the light-emitting layer, and can confine excitons within the light-emitting layer by blocking electron overflow from the light-emitting layer to prevent light emission leakage. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer can function as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have an effect of improving the efficiency and / or the lifespan of the organic electroluminescent device.

[0026] The "electron transport region" means a region in which electrons move between the second electrode and the light-emitting layer, and can include, for example, at least one of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, preferably at least one of an electron buffer layer, an electron transport layer, and an electron injection layer. The electron buffer layer is a layer capable of improving a problem of a change in luminance caused by a change in current characteristics in the device when exposed to high temperature in a panel manufacturing process, which can control the flow of charges.

[0027] The light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer in which two or more layers are stacked. In the light-emitting layer, the doping concentration of the dopant compound with respect to the host compound is preferably less than 20 wt%.

[0028] Hereinafter, the compound represented by Formula 1 will be described in detail.

[0029] In Formula 1 above, Ar1 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; preferably a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted 5- to 25-membered heteroaryl; and more preferably a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted 5- to 18-membered heteroaryl, in which the substituent of the substituted aryl or the substituted heteroaryl can be at least one of (C1-C30)alkyl, (C6-C30)aryl, and 5- to 30-membered heteroaryl. According to one embodiment of the present disclosure, Ar1 can represent a phenyl unsubstituted or substituted with at least one of a methyl group, a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, or an isoquinolyl group; a biphenyl group; a naphthylphenyl group; a phenylnaphthyl group; a fluorenyl group; a dimethylfluorenyl group; a triphenylenyl group; a terphenyl group; a pyridyl unsubstituted or substituted with at least one of a phenyl group, a naphthyl group, or an isoquinolyl group; a dibenzothiophenyl group; a dibenzofuranyl group; or a carbazolyl substituted with one or more phenyl groups.

[0030] According to one embodiment of the present disclosure, Ar1 can be selected from the following structures:

[0031]

[0032] wherein * indicates a bonding site to N.

[0033] In the above structure, at least one carbon atom of the aromatic ring can be replaced with a nitrogen atom. Further, in the above structure, at least one carbon atom of the aromatic ring can be substituted with at least one selected from the group consisting of deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a (C1-C30)alkyl group, a halo(C1-C30)alkyl group, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a (C1-C30)alkoxy group, a (C1-C30)alkylthio group, a (C3-C30)cycloalkyl group, a (C3-C30)cycloalkenyl group, a 3- to 7-membered heterocycloalkyl group, a (C6-C30)aryloxy group, a (C6-C30)arylthio group, a 5- to 30-membered heteroaryl group, a (C6-C30)aryl group, a tri(C1-C30)alkylsilyl group, a tri(C6-C30)arylsilyl group, a di(C1-C30)alkyl(C6-C30)arylsilyl group, a (C1-C30)alkyldi(C6-C30)arylsilyl group, an amino group, a mono- or di- (C1-C30)alkylamino group, a mono- or di- (C6-C30)arylamino group, a (C1-C30)alkyl(C6-C30)arylamino group, a (C1-C30)alkylcarbonyl group, a (C1-C30)alkoxycarbonyl group, a (C6-C30)arylcarbonyl group, a di(C6-C30)arylboronyl group, a di(C1-C30)alkylboronyl group, a (C1-C30)alkyl(C6-C30)arylboronyl group, a (C6-C30)aryl(C1-C30)alkyl group, and a (C1-C30)alkyl(C6-C30)aryl group.

[0034] In Formula 1 above, R1and R2each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; or are linked to one or more adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic 3- to 30-membered alicyclic or aromatic ring, or a combination thereof, where the formed ring can contain at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably a substituted or unsubstituted (C1-C20)alkyl group, or a substituted or unsubstituted (C6-C25)aryl group; and more preferably an unsubstituted (C1-C10)aryl group, or an unsubstituted (C6-C18)aryl group. According to one embodiment of the present disclosure, R1and R2each independently represent a methyl group or a phenyl group. R1and R2may be the same as or different from each other. According to one embodiment of the present disclosure, R1and R2may be the same as each other.

[0035] In the above Formula 1, R3to R7each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano group, a nitro group, or a hydroxyl group; or are linked to one or more adjacent substituents to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, or a combination thereof, where the formed ring can have at least one hetero atom selected from nitrogen, oxygen, and sulfur; and R 11 to R 17 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to one or more adjacent substituents to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, or a combination thereof, where the formed ring can have at least one hetero atom selected from nitrogen, oxygen, and sulfur.

[0036] Preferably, R3to R7each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted 5- to 25-membered heteroaryl, a substituted or unsubstituted (C3-C25)heteroalkyl, or a substituted or unsubstituted (C6-C25)aryl(C1-C20)alkyl; and more preferably hydrogen, deuterium, halogen, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, an unsubstituted 5- to 18-membered heteroaryl, an unsubstituted (C3-C18)cycloalkyl, or an unsubstituted (C6-C18)aryl(C1-C10)alkyl. According to one embodiment of the present disclosure, R3to R7may represent hydrogen.

[0037] In the above Formula 1, a and e each independently represent an integer of 1 to 4, b and c each independently represent an integer of 1 to 3, and d represents an integer of 1 or 2, where if each of a to e is an integer of 2 or more, each of R3to R7may be the same or different. Preferably, a to e each independently represent an integer of 1 or 2. According to one embodiment of the present disclosure, a to e can represent 1.

[0038] In the formulae of the present disclosure, if some substituents are connected with one or more adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic 3- to 30-membered aliphatic ring or aromatic ring, or a combination thereof, the formed ring can contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.

[0039] In the formulae of the present disclosure, the heteroaryl group or the heterocycloalkyl group can contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably N, O, and S. The heteroatom can be bonded to at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino group, a substituted or unsubstituted mono- or di- (C6-C30)arylamino group, and a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group.

[0040] According to one embodiment of the present disclosure, in Formula 1 above, the benzo fluorene-based amine can be bonded to the 2-position or the 3-position of fluorene. Specifically, the compound represented by Formula 1 can be represented by the following Formula 2 or 3:

[0041]

[0042] wherein Ar1, R1 to R7, and a to e are as defined in Formula 1.

[0043] In the present text, "(C1-C30)alkyl" means a straight-chain or branched alkyl group having from 1 to 30 carbon atoms which make up the chain, wherein the number of carbon atoms is preferably from 1 to 20, more preferably from 1 to 10, and includes methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and the like. "(C2-C30)alkenyl" means a straight-chain or branched alkenyl group having from 2 to 30 carbon atoms which make up the chain, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 10, and includes ethenyl, 1 -propenyl, 2-propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. "(C2-C30)alkynyl" means a straight-chain or branched alkynyl group having from 2 to 30 carbon atoms which make up the chain, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 10, and includes ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methylpent-2-ynyl, and the like. "(C3-C30)cycloalkyl" means a monocyclic or polycyclic hydrocarbon having from 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably from 3 to 20, more preferably from 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "3- to 7-membered heterocycloalkyl" means a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, and the like. "(C6-C30)aryl" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having from 6 to 30 ring skeleton carbon atoms, which can be partially saturated and can have a spiro structure, wherein the number of ring skeleton carbon atoms is preferably from 6 to 25, more preferably from 6 to 18, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, "3- to 30-membered heteroaryl" means an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 3 to 30 ring skeleton atoms, which is a monocyclic or a fused ring condensed with at least one benzene ring; can be partially saturated; can be linked to the heteroaryl group or aryl group via one or more single bonds; can have a spiro structure; and includes a monocyclic heteroaryl group including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and a fused ring heteroaryl group including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoaxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinazolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthpyridinyl, carbazolyl, benzocarbazolyl, diphenzenecarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and the like. "Halogen" includes F, Cl, Br, and I.

[0044] In this context, in the expression "substituted or unsubstituted", "substituted" means that a hydrogen atom in certain functional groups is replaced with another atom or functional group (i.e., a substituent). Ar1, R1to R7, and R 11 to R 17In particular embodiments, each substituent of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted heterocycloalkyl, the substituted arylalkyl, or the substituted mono- or polycyclic alicyclic or aromatic ring, or combinations thereof, is independently at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, 3- to 7-membered heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, 5- to 30-membered heteroaryl unsubstituted or substituted with one or more (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with one or more 5- to 30-membered heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyl di(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl; preferably at least one selected from the group consisting of (C1-C20)alkyl, (C6-C25)aryl, and 5- to 25-membered heteroaryl; more preferably at least one selected from the group consisting of (C1-C10)alkyl, (C6-C18)aryl, and 5- to 18-membered heteroaryl; and, for example, at least one selected from the group consisting of methyl, phenyl, naphthyl, pyridyl, quinolyl, and isoquinolyl.

[0045] The compound represented by Formula 1 includes the following compounds, but is not limited thereto:

[0046]

[0047]

[0048]

[0049] The compound of formula (1) according to the present disclosure can be prepared by synthetic methods known to one skilled in the art. For example, it can be prepared according to the following Reaction Scheme 1, but is not limited thereto:

[0050] [Reaction Scheme 1]

[0051]

[0052] wherein Ar1, R1 to R7, and a to e are as defined in formula 1.

[0053] The present disclosure can provide an organic electroluminescent material including at least one organic electroluminescent compound represented by formula 1, and an organic electroluminescent device including the same. According to one embodiment of the present disclosure, a hole transport material including at least one compound represented by formula 1 can be provided.

[0054] The organic electroluminescent material can include only the organic electroluminescent compound according to the present disclosure, or can further include a conventional material for an organic electroluminescent material.

[0055] The present disclosure can provide an organic electroluminescent device including at least one organic electroluminescent compound represented by formula 1. According to one embodiment of the present disclosure, the organic electroluminescent device can include at least one compound represented by formula 1 in a hole transport region or in at least one layer of a plurality of hole transport layers.

[0056] Host compounds that can be used in combination with the compound of the present disclosure include a compound represented by any one of the following formulas 11 to 13, but are not limited thereto:

[0057]

[0058] wherein

[0059] Ma represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di-(C6-C30)aryl amino, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

[0060] La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

[0061] A represents S, O, N(Re), or C(Rf)(Rg);

[0062] Ra to Rd each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyl di(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered, aliphatic ring or aromatic ring, or a combination thereof, wherein the formed ring can contain at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0063] Re to Rg each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyl di(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino group, a substituted or unsubstituted mono- or di- (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylaminogroup; or Rf and Rg are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, 3- to 30-membered, aliphatic ring or aromatic ring, or a combination thereof, wherein the formed ring can contain at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0064] w to y each independently represent an integer of 1 to 4, and z represents an integer of 1 to 3; and

[0065] The heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P.

[0066] The compound represented by any one of Formulae 11 to 13 includes the following compounds, but is not limited thereto:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] wherein TPS represents triphenylsilyl group.

[0074] The dopant compound that can be used in combination with the compound of the present disclosure includes a compound represented by the following formula 101, but is not limited thereto:

[0075]

[0076] wherein

[0077] L is selected from the following structures:

[0078]

[0079] R 100 to R 103 each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl unsubstituted or substituted with one or more halogens, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted 3- to 30-membered heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; or R 100 to R 103 may be linked to adjacent R 100 to R 103 to form a fused ring of substituted or unsubstituted pyridine, for example, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuro[3,2-g]pyridine, substituted or unsubstituted benzothieno[3,2-g]pyridine, substituted or unsubstituted indeno[1,2-g]pyridine, substituted or unsubstituted benzofuro[3,2-g]quinoline, substituted or unsubstituted benzothieno[3,2-g]quinoline, or substituted or unsubstituted indeno[1,2-g]quinoline;

[0080] R 104 to R 107 each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl unsubstituted or substituted with one or more halogens, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R107 may be linked to adjacent R 104 to R 107 to form a substituted or unsubstituted fused ring with benzene, for example, a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothiopyridine;

[0081] R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with one or more halogens, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or R 201 to R 211 may be linked to adjacent R 201 to R 211 to form a substituted or unsubstituted fused ring; and

[0082] n represents an integer of 1 to 3.

[0083] Specifically, the dopant compound includes the following compounds, but is not limited thereto:

[0084]

[0085]

[0086]

[0087]

[0088] To form each layer constituting the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc., can be used.

[0089] When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvent, which does not cause any problem in forming the layer.

[0090] The present disclosure can provide a display system including at least one organic electroluminescent compound represented by Formula 1. That is, by using the organic electroluminescent compound of the present disclosure, a display system or a lighting system can be produced. Specifically, by using the organic electroluminescent compound of the present disclosure, a display system, for example, for a smartphone, a tablet, a notebook, a PC, a TV, or a vehicle, or a lighting system, for example, an indoor or outdoor lighting system, can be produced.

[0091] Hereinafter, the preparation method of the organic electroluminescent compound of the present disclosure, and the physical properties of the compound will be explained in detail with reference to representative compounds of the present disclosure. However, the following examples are intended to explain the present disclosure, and the present disclosure is not limited thereto.

[0092] Example 1 : Preparation of compound C-4

[0093]

[0094] Into a reaction vessel were introduced 10 g of compound a-1 (31 mmol), 11.2 g of compound b-1 (31 mmol), 1.42 g of tris(dibenzylideneacetone)dipalladium(0) (1.6 mmol), 1.6 mL of tri-tert-butylphosphine (3.1 mmol, 50% toluene solution), 5.9 g of sodium tert-butoxide (62 mmol), and 154 mL of toluene, and the mixture was refluxed for 4 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 8.3 g of compound C-4 (yield: 44%).

[0095] Example 2: Preparation of compound C-5

[0096]

[0097] Into a reaction vessel were introduced 7.0 g of compound a-1 (22 mmol), 8.6 g of compound b-2 (24 mmol), 0.60 g of tris(dibenzylideneacetone)dipalladium(0) (0.66 mmol), 0.6 mL of tri-tert-butylphosphine (1.32 mmol, 50% toluene solution), 3.1 g of sodium tert-butoxide (32 mmol), and 110 mL of toluene, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 0.9 g of compound C-5 (yield: 7%).

[0098] Example 3: Preparation of compound C-6

[0099]

[0100] Into a reaction vessel were introduced 7.4 g of compound a-1 (23 mmol), 10.0 g of compound b-3 (23 mmol), 1.0 g of tris(dibenzylideneacetone)dipalladium(0) (1.2 mmol), 1.1 mL of tri-tert-butylphosphine (2.3 mmol, 50% toluene solution), 4.4 g of sodium tert-butoxide (46 mmol), and 114 mL of toluene, and the mixture was refluxed for 5 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 4.9 g of compound C-6 (yield: 31%).

[0101] Example 4: Preparation of compound C-7

[0102]

[0103] Into a reaction vessel were introduced 7.0 g of compound a-1 (22 mmol), 9.8 g of compound b-4 (24 mmol), 0.6 g of tris(dibenzylideneacetone)dipalladium(0) (0.66 mmol), 0.6 mL of tri-tert-butylphosphine (1.32 mmol, 50% toluene solution), 3.1 g of sodium tert-butoxide (32 mmol), and 110 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 2.8 g of compound C-7 (yield: 20%).

[0104] Example 5: Preparation of compound C-8

[0105]

[0106] Into a reaction vessel were introduced 10.0 g of compound a-1 (31 mmol), 12.7 g of compound b-5 (24 mmol), 1.42 g of tris(dibenzylideneacetone)dipalladium(0) (1.6 mmol), 1.6 mL of tri-tert-butylphosphine (3.1 mmol, 50% toluene solution), 5.9 g of sodium tert-butoxide (62 mmol), and 154 mL of toluene, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 2 g of compound C-8 (yield: 10%).

[0107] Example 6: Preparation of compound C-24

[0108]

[0109] Into a reaction vessel were introduced 13 g of compound a-1 (40 mmol), 19.5 g of compound b-6 (40 mmol), 1.11 g of tris(dibenzylideneacetone)dipalladium(0) (1.2 mmol), 1.2 mL of tri-tert-butylphosphine (2.4 mmol, 50% toluene solution), 5.8 g of sodium tert-butoxide (60 mmol), and 223 mL of toluene, and the mixture was refluxed for 4 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 15 g of compound C-24 (yield: 51%).

[0110] Example 7: Preparation of compound C-2

[0111]

[0112] Into a reaction vessel were introduced 10 g of compound a-1 (31 mmol), 12.3 g of compound b-7 (34 mmol), 1.42 g of tris(dibenzylideneacetone)dipalladium(0) (1.6 mmol), 1.6 mL of tri-tert-butylphosphine (3.1 mmol, 50% toluene solution), 4.5 g of sodium tert-butoxide (46 mmol), and 160 mL of toluene, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 6.3 g of compound C-2 (yield: 34%).

[0113] Example 8: Preparation of compound C-25

[0114]

[0115] Into a reaction vessel were introduced 6 g of compound a-1 (19 mmol), 9.9 g of compound b-8 (20 mmol), 0.85 g of tris(dibenzylideneacetone)dipalladium(0) (0.93 mmol), 0.75 mL of tri-tert-butylphosphine (0.19 mmol, 50% o-xylene solution), 2.7 g of sodium tert-butoxide (28 mmol), and 93 mL of toluene, and the mixture was refluxed for 1.5 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 2.6 g of compound C-25 (yield: 19%).

[0116] Example 9: Preparation of compound C-66

[0117]

[0118] Into a reaction vessel were introduced 8 g of compound a-1 (25 mmol), 9.9 g of compound b-9 (25 mmol), 1.13 g of tris(dibenzylideneacetone)dipalladium(0) (1.25 mmol), 1 mL of tri-tert-butylphosphine (2.5 mmol, 50% o-xylene solution), 5.9 g of sodium tert-butoxide (62 mmol), and 125 mL of toluene, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 11 g of compound C-66 (yield: 69%).

[0119] Example 10: Preparation of compound C-62

[0120]

[0121] Into a reaction vessel were introduced 3.9 g of compound a-1 (12 mmol), 5.3 g of compound b-10 (12 mmol), 0.56 g of tris(dibenzylideneacetone)dipalladium(0) (0.6 mmol), 0.5 mL of tri-tert-butylphosphine (1.2 mmol, 50% o-xylene solution), 2.3 g of sodium tert-butoxide (24 mmol), and 61 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 5.3 g of compound C-62 (yield: 64%).

[0122] Example 11 : Preparation of compound C-61

[0123]

[0124] Into a reaction vessel were introduced 7.9 g of compound a-1 (24 mmol), 8.0 g of compound b-11 (22 mmol), 1.0 g of tris(dibenzylideneacetone)dipalladium(0) (1.1 mmol), 1 mL of tri-tert-butylphosphine (2.2 mmol, 50% o-xylene solution), 3.2 g of sodium tert-butoxide (33 mmol), and 110 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 8.5 g of compound C-61 (yield: 64%).

[0125] Example 12: Preparation of compound C-63

[0126]

[0127] Into a reaction vessel were introduced 8.6 g of compound a-1 (26 mmol), 12.0 g of compound b-12 (29 mmol), 1.2 g of tris(dibenzylideneacetone)dipalladium(0) (1.3 mmol), 1.3 mL of tri-tert-butylphosphine (2.6 mmol, 50% o-xylene solution), 3.8 g of sodium tert-butoxide (40 mmol), and 133 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 11 g of compound C-63 (yield: 64%).

[0128] Example 13: Preparation of compound C-67

[0129]

[0130] Into a reaction vessel were introduced 14.1 g of compound a-1 (44 mmol), 18.0 g of compound b-13 (44 mmol), 0.49 g of palladium(II) acetate (2.2 mmol), 1.8 mL of tri-tert-butylphosphine (4.4 mmol, 50% o-xylene solution), 9.2 g of sodium tert-butoxide (96 mmol), and 200 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 3.5 g of compound C-67 (yield: 12%).

[0131] Example 14: Preparation of compound C-68

[0132]

[0133] Into a reaction vessel were introduced 4 g of compound a-1 (12 mmol), 5.1 g of compound b-14 (12 mmol), 0.57 g of tris(dibenzylideneacetone)dipalladium(0) (0.6 mmol), 0.51 g of SPhos (1.2 mmol), 3.0 g of sodium tert-butoxide (3.1 mmol), and 60 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 6.1 g of compound C-68 (yield: 75%).

[0134] Example 15: Preparation of compound C-69

[0135]

[0136] Into a reaction vessel were introduced 44.6 g of compound a-1 (138 mmol), 34.7 g of compound b-15 (166 mmol), 1.55 g of palladium (II) acetate (6.9 mmol), 6.8 mL of tri-tert-butylphosphine (13.8 mmol, 50% o-xylene solution), 26.5 g of sodium tert-butoxide (276 mmol), and 690 mL of toluene, and the mixture was refluxed for 8 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 12 g of compound a-2 (yield: 19%). Thereafter, into a reaction vessel were introduced 6 g of compound a-2 (13 mmol), 4.2 g of compound b-15a (16 mmol), 0.61 g of tris(dibenzylideneacetone)dipalladium(0) (0.65 mmol), 0.66 mL of tri-tert-butylphosphine (1.3 mmol, 50% o-xylene solution), 1.9 g of sodium tert-butoxide (1.95 mmol), and 66 mL of toluene, and the mixture was refluxed for 0.5 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 6.8 g of compound C-69 (yield: 81%).

[0137] Example 16: Preparation of compound C-70

[0138]

[0139] Into a reaction vessel were introduced 21 g of compound a-2 (46 mmol), 11.4 g of compound b-16 (46 mmol), 0.52 g of palladium (II) acetate (2.3 mmol), 1.9 mL of tri-tert-butylphosphine (4.6 mmol, 50% o-xylene solution), 9.8 g of sodium tert-butoxide (102 mmol), and 230 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 2.5 g of compound C-70 (yield: 8.7%).

[0140] Example 17: Preparation of compound C-71

[0141]

[0142] Into a reaction vessel were introduced 6 g of compound a-2 (13 mmol), 4.2 g of compound b-17 (16 mmol), 0.61 g of tris(dibenzylideneacetone)dipalladium(0) (0.65 mmol), 0.66 mL of tri-tert-butylphosphine (1.3 mmol, 50% o-xylene solution), 1.9 g of sodium tert-butoxide (1.95 mmol), and 66 mL of toluene, and the mixture was refluxed for 0.5 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 4.5 g of compound C-71 (yield: 53%).

[0143] Example 18: Preparation of compound C-10

[0144]

[0145] Into a reaction vessel were introduced 5.1 g of compound a-1 (16 mmol), 6.9 g of compound b-18 (16 mmol), 0.72 g of tris(dibenzylideneacetone)dipalladium(0) (0.80 mmol), 0.65 g of SPhos (1.6 mmol), 3.8 g of sodium tert-butoxide (3.9 mmol), and 72 mL of toluene, and the mixture was refluxed for 0.5 hours. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 6.9 g of compound C-10 (yield: 64%).

[0146] Example 19: Preparation of compound C-72

[0147]

[0148] Into a reaction vessel were introduced 5.0 g of compound a-1 (15 mmol), 6.8 g of compound b-19 (15 mmol), 0.17 g of palladium(II) acetate (0.75 mmol), 0.64 g of SPhos (1.5 mmol), 3.7 g of sodium tert-butoxide (3.9 mmol), and 77 mL of toluene, and the mixture was refluxed for 1 hour. The reaction solution was cooled to room temperature, and then the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 1.5 g of compound C-72 (yield: 14%).

[0149] The physical properties of the compounds prepared in these examples are shown in Table 1 below.

[0150] [Table 1]

[0151]

[0152] Hereinafter, whether the driving voltage, luminous efficiency, and lifespan characteristics of an organic light-emitting diode device (OLED device) can be improved by including a compound represented by Formula 1 is discussed. However, the following examples aim to explain the characteristics of an OLED device including a compound according to the present disclosure, and the present disclosure is not limited thereto.

[0153] Device Examples 1 to 14: Production of OLED devices according to the present disclosure

[0154] An OLED device including an organic electroluminescent compound according to the present disclosure was produced as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED device (Geomatec, Japan) was subjected to ultrasonic washing with acetone and isopropanol in this order, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the apparatus chamber was controlled to 10 -6 After that, a current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 90 nm on the ITO substrate. Compound HI-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. The second hole transport layer (auxiliary layer) compounds shown in Table 2 below were introduced into another cell of the vacuum vapor deposition apparatus, and the compounds were evaporated by applying a current to the cell, thereby forming a second hole transport layer (auxiliary layer) having a thickness of 60 nm on the first hole transport layer. After the formation of the hole injection layer and the hole transport layer, the light-emitting layer was then deposited as follows. Compound H-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated and deposited at a doping amount (amount of dopant) of 2 wt% based on the total amount of the dopant and the host, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Then, compounds ET-1 and EI-1 were introduced into two other cells, evaporated at a rate of 1:1, and deposited, to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. Next, after depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thereby, an OLED device was produced.

[0155] Comparative Examples 1 to 7: Production of OLED devices not according to the present disclosure

[0156] An OLED device was produced in the same manner as in Device Example 1, except that the compound shown in Table 2 below was used for the second hole transport layer.

[0157] The compounds used in Device Examples 1 to 14 and Comparative Examples 1 to 7 are as follows.

[0158]

[0159] In addition, the driving voltage, luminous efficiency, and CIE color coordinates of the OLED devices produced in Device Examples 1 to 14 and Comparative Examples 1 to 7 at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 99% at a luminance of 5,000 nits and constant current (useful life; T99) are provided in Table 2 below.

[0160] [Table 2]

[0161]

[0162] The LUMO energy value, HOMO energy value, and triplet energy value of the compound included in the second hole transport layer of Device Examples 1 to 14 and Comparative Examples 1 and 7 are provided in Table 3 below. The HOMO energy value and LUMO energy value of the present disclosure were measured by using density functional theory (DFT) in the Gaussian 09 program of Gaussian, Inc., but are not limited thereto. The triplet energy value of the present disclosure was measured by using time-dependent density functional theory (TD-DFT) in the Gaussian 09 program in the structure of the isomer having the lowest energy, but is not limited thereto. Specifically, the HOMO energy value and LUMO energy value in the device examples and comparative examples were obtained from the structure having the lowest energy among the calculated conformational isomer energies after structure optimization of all possible conformational isomer structures at the B3LYP / 6-31g* level.

[0163] [Table 3]

[0164] Compound LUMO (eV) HOMO (eV) Triplet energy (eV) C-2 -1.242 -4.844 2.505 C-4 -1.250 -4.790 2.503 C-5 -1.235 -4.816 2.503 C-6 -1.238 -4.831 2.504 C-7 -1.254 -4.795 2.498 C-8 -1.247 -4.830 2.504 C-24 -1.228 -4.802 2.504 C-25 -1.230 -4.846 2.504 C-66 -1.239 -4.718 2.499 C-62 -1.299 -4.891 2.506 C-61 -1.224 -4.884 2.507 C-63 -1.252 -4.838 2.499 C-67 -1.238 -4.892 2.507 C-68 -1.232 -4.823 2.435 C-69 -1.267 -4.886 2.506 C-70 -1.213 -4.816 2.503 C-71 -1.265 -4.853 2.502 C-10 -1.243 -4.764 2.503 C-72 -1.194 -4.792 2.496 T-1 -1.242 -4.752 2.377 T-2 -1.283 -4.754 2.371 T-3 -1.216 -4.770 2.384 T-4 -1.245 -4.767 2.381 T-5 -1.268 -4.868 2.505 T-6 -0.815 -4.826 2.705 T-7 -1.004 -4.744 2.590

[0165] As can be seen from Device Examples 1 to 14 and Comparative Examples 1 to 4 of Tables 2 and 3, the compounds of the present disclosure in which the fluorene amine is bonded to the 3-position of the benzofluorene have higher triplet energy values than the compounds of Comparative Examples 1 to 4 in which the fluorene amine is bonded to the 2-position of the benzofluorene, and the OLED devices comprising the compounds of the present disclosure exhibit higher luminous efficiency and longer lifespan characteristics than the OLED devices of Comparative Examples 1 to 4. It is understood that this is because the compounds of the present disclosure in which the fluorene amine is bonded to the 3-position of the benzofluorene have a reduced range of the HOMO orbital of the benzofluorene, the transition distance between molecules is increased, and thus the hole mobility is reduced, as compared to the compounds in which the fluorene amine is bonded to the 2-position of the benzofluorene. That is, it is understood that the compounds of the present disclosure in which the fluorene amine is bonded to the 3-position of the benzofluorene have reduced hole mobility, charge balance in the light-emitting layer is improved, and thereby the luminous efficiency of the OLED devices comprising the compounds of the present disclosure is improved.

[0166] Further, as can be seen from Device Examples 1 to 14 and Comparative Example 5 of Tables 2 and 3, the compounds of the present disclosure in which the benzofluorene is bonded to the fluorene amine have higher HOMO energy values than the compounds of Comparative Example 5 in which the benzofluorene is bonded to the amine not containing fluorene, and the OLED devices comprising the compounds of the present disclosure exhibit lower driving voltage and longer lifespan characteristics than the OLED devices of Comparative Example 5, while having similar luminous efficiency.

[0167] Further, as can be seen from Device Examples 1 to 14 and Comparative Examples 6 and 7 of Tables 2 and 3, the benzofluorene amine-containing compounds of the present disclosure have lower LUMO energy values than the fluorene amine-containing compounds of Comparative Examples 6 and 7, and the OLED devices comprising the compounds of the present disclosure exhibit longer lifespan characteristics than the OLED devices of Comparative Examples 6 and 7, while having lower driving voltage or higher luminous efficiency.

Claims

1. An organic electroluminescent compound represented by the following Formula 1: wherein Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; R 1 and R 2 each independently represent a substituted or unsubstituted (C6-C30)aryl; R3to R7each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano group, a nitro group, or a hydroxyl group; R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47, R48, R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61 R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; and a and e each independently represent an integer of 1 to 4, b and c each independently represent an integer of 1 to 3, and d represents an integer of 1 or 2, wherein if each of a to e is an integer of 2 or more, each of R 3 to R 7 can be the same or different; In Ar1, R1to R7, and R 11 to R 17 In the substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocycloalkyl, or substituted arylalkyl, the substituents are each independently at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, 3- to 7-membered heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, 5- to 30-membered heteroaryl unsubstituted or substituted with (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with 5- to 30-membered heteroaryl, amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

2. The organic electroluminescence compound according to claim 1, wherein Formula 1 is represented by the following Formula 2 or 3: wherein Ar 1, R 1 to R 7, and a to e are as defined in claim 1.

3. The organic electroluminescent compound according to claim 1, wherein Ar 1 is selected from the following structures: wherein * represents a bonding site to N, and at least one carbon atom of the aromatic ring can be replaced with a nitrogen atom.

4. The organic electroluminescent compound according to claim 1, wherein The compound represented by Formula 1 is selected from the group consisting of: 5.An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1. 6.An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

7. An organic electroluminescent device, wherein The organic electroluminescent compound of claim 1 is contained in a hole transport region.

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