JP7402831B2 - Organic electroluminescent compound and organic electroluminescent device containing the same - Google Patents

Description

The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same.

A green-emitting TPD/Alq ₃ bilayer small molecule organic electroluminescent device composed of an emissive layer and a charge transport layer was first developed in 1987 by Eastman Kodak's Tang et al. Since then, research on organic electroluminescent devices has been rapidly commercialized. Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying electricity to an organic electroluminescent material and typically include an anode, a cathode, and an organic layer formed between two electrodes. Organic electroluminescent devices have a multilayer structure comprising a hole transport band, an emissive layer, an electron transport band, etc. to improve their efficiency and stability.

Furthermore, since the performance of an organic electroluminescent device is highly dependent on the compounds contained in each zone or layer thereof, there has been active research into new compounds that can improve the performance of organic electroluminescent devices. For example, 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. It has been used as a compound in the hole transport band in organic electroluminescent devices. However, organic electroluminescent devices using these materials suffer from reduced luminous efficiency and lifetime. That is because when organic electroluminescent devices are driven under high current, thermal stress will occur between the anode and the hole injection layer, thereby such thermal stress will significantly reduce the lifetime of the device. . Furthermore, because the organic materials used in the hole transport band have extremely high hole mobility, the charge balance between holes and electrons is disrupted, leading to a decrease in quantum efficiency (cd/A). . Therefore, there is a need for new compounds that can replace traditional compounds used in the hole transport band. In addition, research has been conducted on various materials and devices to improve the luminous efficiency, driving voltage, and/or lifetime characteristics of organic electroluminescent devices.

Korean Patent Application Publication No. 2017-0096770A discloses a compound in which an amine is bonded to a specific position of benzonaphthothiophene or benzonaphthofuran as a compound included in the hole transport layer of an organic electroluminescent device. It's just that.

It is an object of the present disclosure to provide organic electroluminescent compounds useful for manufacturing organic electroluminescent devices with low driving voltage and/or high luminous efficiency and/or long lifetime.

The present inventors have demonstrated that, compared to the compound disclosed in Korean Patent Application Publication No. 2017-0096770A, the degree of free rotation is reduced due to steric hindrance of the molecule without significantly changing the triplet energy. It has been found that the above object can be achieved and the present invention can be completed by using an organic electroluminescent compound represented by the following formula 1 that increases molecular rigidity.

In equation 1,
X represents O or S;
Ar ₁ to Ar ₄ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30) member) heteroaryl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1- C30) represents alkyl (C6-C30) arylamino; or Ar ₁ and Ar ₂ and Ar ₃ and Ar ₄ may be linked to each other to form a ring;
L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) C30) alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or substituted or unsubstituted (C1-C30) C30) represents alkyl (C6-C30) arylamino;
a represents an integer from 1 to 4, b represents an integer from 1 to 5, and when a and b are 2 or more, each R ₁ and each R ₂ may be the same or different. ;
p and q each independently represent 0 or 1 on the condition that the sum of p and q is 1 or 2, and when the sum of p and q is 2, L ₁ and L ₂ , and Ar ₁ to Ar ₄ may be the same or different.

Advantageous Effects of the Invention Organic electroluminescent compounds according to the present disclosure can provide organic electroluminescent devices with low driving voltage, high luminous efficiency, and/or long lifetime.

The present disclosure will be described in detail below. However, the following description is intended to be illustrative of the invention and is not meant to limit the scope of the invention in any way.

The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and optionally included in any material layer that makes up the organic electroluminescent device.

The term "organic electroluminescent material" in this disclosure means a material that can be used in an organic electroluminescent device and that can include at least one compound. The organic electroluminescent material may be included in any layer making up the organic electroluminescent device, if desired. For example, organic electroluminescent materials may be hole-injecting materials, hole-transporting materials, hole-assisting materials, luminescent-assisting materials, electron-blocking materials, luminescent materials, electron-buffering materials, hole-blocking materials, electron-transporting materials, or electron-transporting materials. It may be an injection material or the like.

The term "hole transport zone" means the zone in which holes move between the first electrode and the emissive layer. For example, the hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole assist layer, an emission assist layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the emission auxiliary layer, and the electron blocking layer may each be a single layer, or may be a multilayer of two or more layers. good. According to one embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer. The second hole transport layer can be at least one layer of a plurality of hole transport layers and can include at least one of a hole assisting layer, an emission assisting layer, and/or an electron blocking layer. Additionally, according to another embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer. The first hole transport layer may be disposed between the first electrode and the emissive layer, and the second hole transport layer may be disposed between the first hole transport layer and the emissive layer. . The second hole transport layer may have the role of a hole transport layer, a luminescence auxiliary layer, a hole auxiliary layer, and/or an electron blocking layer.

The hole transport layer may be disposed between the anode (or hole injection layer) and the light emitting layer, and smoothly moves the holes transmitted from the anode to the light emitting layer, and transfers the holes transmitted from the cathode to the light emitting layer. It can function to block the light and keep it in the light emitting layer. The luminescence auxiliary layer may be arranged between the anode and the luminescent layer or between the cathode and the luminescent layer. If a luminescence auxiliary layer is placed between the anode and the luminescent layer, it can be used to promote hole injection and/or hole transport or to prevent electron overflow. If a luminescence auxiliary layer is placed between the cathode and the luminescent layer, it can be used to promote electron injection and/or electron transport or to prevent hole overflow. In addition, a hole assisting layer can be disposed between the hole transport layer (or hole injection layer) and the emissive layer and is effective to promote or inhibit the hole transport rate (or hole injection rate). , thereby allowing the charge balance to be controlled.

Additionally, an electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the emissive layer and confine excitons within the emissive layer by blocking the overflow of electrons from the emissive layer. Light leakage can be prevented. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can be used as luminescence auxiliary layers, hole auxiliary layers, electron blocking layers, etc. The luminescence auxiliary layer, hole auxiliary layer and/or electron blocking layer may have the effect of improving the luminous efficiency and/or lifetime of the organic electroluminescent device.

As used herein, "(C1-C30)alkyl" means a straight-chain or branched alkyl having 1 to 30 carbon atoms in the chain, where the number of carbon atoms is: The number is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. "(C2-C30)alkenyl" is a straight-chain or branched alkyl having 1 to 30 carbon atoms in the chain, and the number of carbon atoms is preferably 2 to 20, more preferably 2 to 30. These include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. "(C2-C30)alkynyl" is a straight-chain or branched alkynyl having 2 to 30 carbon atoms constituting the chain, and the number of carbon atoms is preferably 2 to 20, more preferably 2 to 30. These include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30)cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, more preferably is 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. "(3-7 membered)heterocycloalkyl" means 3 containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N. It is a cycloalkyl having ~7 ring skeleton atoms, and the number of ring skeleton atoms is preferably 5 to 7. Examples of the heterocycloalkyl include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran. "(C6-C30)aryl(ene)" is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms, and the number of ring carbon atoms is , preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may contain a spiro structure. Examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo Fluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzocrysenyl, Examples include naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azulenyl, and the like. More specifically, aryl includes o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-tolyl, -cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4''-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl- 3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9 -dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9 -diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl , 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2 -triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, and the like.

In the present specification, "(3-30 membered) heteroaryl(ene)" is at least one member selected from the group consisting of B, N, O, S, Si, P, and Ge, preferably 1-4 Aryl having 3 to 30 ring skeleton atoms, including 5 to 30 heteroatoms, and the number of ring skeleton atoms is preferably 5 to 25. The heteroaryl may be a monocyclic ring or a fused ring fused to at least one benzene ring; it may also be partially saturated. The above hetero atoms include hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) C30) alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono - or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino may be linked to at least one substituent selected from the group consisting of: Furthermore, the above heteroaryl may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond; it may also contain a spiro structure. Examples of heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, Monocyclic heteroaryl such as pyridazinyl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, Examples include fused ring heteroaryls such as benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl, and germafluorenyl. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1- Indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazo Pyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6- Benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2- Quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, Azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1 -phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9- Phenantridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5- Oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-t-butylpyrrol-4-yl, 3-( 2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1 -indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl , 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germa It may also be fluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, and the like. "Halogen" includes F, Cl, Br, and I.

As used herein, "ortho (o)", "meta (m)" and "para (p)" are meant to indicate the substitution positions of all substituents. The ortho position is, for example, a compound having substituents adjacent to each other in the 1- and 2-positions of benzene. The meta position is the next substitution position after the immediately adjacent substitution position, for example in compounds having substituents at the 1st and 3rd positions of benzene. The para position is the next substitution position after the meta position, and is, for example, a compound having substituents at the 1st and 4th positions of benzene.

Furthermore, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced by another atom or another functional group, ie, a substituent. Substituted (C1-C30) alkyl, substituted (C6-C30) aryl (ene), substituted (3-30 membered) heteroaryl (ene), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tri(C6-C30)arylsilyl, The substituents of substituted mono- or di-(C1-C30) alkylamino, substituted mono- or di-(C6-C30) arylamino, and substituted (C1-C30) alkyl (C6-C30) arylamino are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (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, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-30 membered) heteroaryl, (3-30 membered) heteroaryl substituted or unsubstituted (C6-C30) aryl, tri(C1-C30) alkylsilyl, tri(C6 -C30) arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, (C1-C30) Alkyl substituted or unsubstituted 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) )ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment, the substituents each independently represent (C1-C20)alkyl and/or (C6-C25)aryl. According to another embodiment, the substituents each independently represent at least one of (C1-C10)alkyl and (C6-C18)aryl. For example, each substituent can be independently at least one of methyl, phenyl, naphthyl, and biphenyl.

As used herein, "a ring formed by bonding to adjacent substituents" refers to a substituted or unsubstituted (3 to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or It refers to a combination of these and is formed by linking or condensing two or more adjacent substituents; preferably a substituted or unsubstituted (3 to 26 membered) monocyclic or polycyclic aliphatic ring. , an aromatic ring, or a combination thereof. Furthermore, the ring formed may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S.

In the formulas of the present disclosure, heteroaryl(ene) and heterocycloalkyl each independently contain at least one heteroatom selected from the group consisting of B, N, O, S, SiP, and Ge. It's okay to stay. Furthermore, the above heteroatoms include hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl. , substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6 ~C30) arylsilyl, substituted or unsubstituted (C1~C30)alkyldi(C6~C30)arylsilyl, substituted or unsubstituted tri(C6~C30)arylsilyl, substituted or unsubstituted mono- or di(C1~C30) C30) at least selected from the group consisting of alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino It may be linked to one substituent.

The compound represented by Formula 1 can be represented by any one of Formulas 2 to 4 below.

In formulas 2 to 4, X, Ar ₁ to Ar ₄ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, p, and q are as defined in formula 1. According to one embodiment, the sum of p and q may be one.

In formulas 1 to 4, X represents O or S.

In formulas 1 to 4, Ar ₁ to Ar ₄ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (C6 to C30) aryl. Substituted (3-30 membered) heteroaryl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or It represents unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or Ar ₁ and Ar ₂ may be connected to each other to form a ring, and Ar ₃ and Ar ₄ may be connected to each other to form a ring. It may form a ring. According to one embodiment, Ar ₁ to Ar ₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-25 membered) heteroaryl, substituted or unsubstituted mono- or di-(C1-C20) alkylamino, substituted or unsubstituted mono- or di-(C6-C25) arylamino, or substituted or unsubstituted (C1 -C20) represents alkyl (C6-C25) arylamino. According to another embodiment, Ar ₁ -Ar ₄ are each independently substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- 25-membered) represents a heteroaryl. For example, Ar ₁ to Ar ₄ each independently represent unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted phenanthrenyl, unsubstituted naphthylphenyl, phenyl-substituted or unsubstituted dimethylfluorenyl, unsubstituted diphenylfluorenyl, phenyl, unsubstituted terphenyl, spirobifluorenyl, phenyl-substituted or unsubstituted dibenzothiophenyl, dibenzofuranyl, or carbazolyl substituted with at least one phenyl and/or at least one biphenyl.

According to one embodiment, Ar ₁ and Ar ₂ or Ar ₃ and Ar ₄ can each be independently selected from the following group: For example, when Ar ₁ is phenyl, Ar ₂ may be any one of the following compounds.

In formulas 1 to 4, L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene; According to the form, L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (3-25 membered) heteroarylene; According to the form, L ₁ and L ₂ each independently represent a single bond, an unsubstituted (C6 to C18) arylene, or an unsubstituted (3 to 18 membered) heteroarylene. For example, L ₁ and L ₂ may each independently be a single bond, unsubstituted phenylene, or unsubstituted naphthylene.

In formulas 1 to 4, R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkylsilyl Unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; according to one embodiment, R ₁ and R ₂ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted represents substituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-25 membered) heteroaryl; according to another embodiment, R ₁ and R ₂ are Each independently represents hydrogen, deuterium, halogen, cyano, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl. For example, R ₁ and R ₂ can be hydrogen.

In formulas 1 to 4, a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are each 2 or more, each R ₁ and each R ₂ are the same. may also be different; according to one embodiment, a and b may be 1.

In formulas 1 to 4, p and q each independently represent 0 or 1 on the condition that the sum of p and q is 1 or 2, and when the sum of p and q is 2, each The substituents may be the same or different; according to one embodiment, the sum of p and q may be 1. For example, if p is 0, q is 1; if p is 1, q is 0.

The compound represented by Formula 1 can be more specifically represented by the following compounds, but is not limited thereto.

The organic electroluminescent compounds of the present disclosure can be made by synthetic methods known to those skilled in the art. For example, the organic electroluminescent compounds of the present disclosure can be synthesized as shown in Reaction Schemes 1 to 3 below, but are not limited thereto.

[Reaction scheme 1]

[Reaction scheme 2]

[Reaction scheme 3]

In Reaction Schemes 1 to 3, X, Ar ₁ to Ar ₄ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, p, and q are as defined in Formula 1.

As mentioned above, exemplary syntheses of compounds represented by formulas 2-4 according to one embodiment are described, which include Buchwald-Hartwig cross-coupling reactions, Wittig reactions, Ullmann coupling reactions. , Suzuki cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, It is based on cyclic dehydration reactions, SN ₁ -substitution reactions, SN ₂ -substitution reactions, and phosphine-mediated reductive cyclization reactions. It will be understood by those skilled in the art that the above reaction will proceed even when other substituents defined in Formulas 2 to 4 other than the substituents described in the specific synthesis examples are attached. .

Dopants that can be used in combination with the compounds of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant is a metallized complex compound of a metal atom selected from, but not limited to, iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably iridium (Ir). , osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallated iridium complex compound.

（式中、Ｌは以下の構造１又は２：

から選択され、Ｒ_１００は、それぞれ独立して、水素、重水素、置換若しくは無置換（Ｃ１～Ｃ３０）アルキル、又は置換若しくは無置換（Ｃ３～Ｃ３０）シクロアルキルを表し；
Ｒ_１０１～Ｒ_１０９及びＲ_１１１～Ｒ_１２３は、それぞれ独立して、水素、重水素、ハロゲン、重水素若しくはハロゲン置換若しくは無置換（Ｃ１～Ｃ３０）アルキル、置換若しくは無置換（Ｃ３～Ｃ３０）シクロアルキル、置換若しくは無置換（Ｃ６～Ｃ３０）アリール、シアノ、又は置換若しくは無置換（Ｃ１～Ｃ３０）アルコキシを表すか；又は隣接する置換基と連結して環を形成していてもよく；具体的にはＲ_１０６～Ｒ_１０９は、隣接する置換基に結合して、環、例えばアルキル置換若しくは無置換インデン環、アルキル置換若しくは無置換ベンゾチオフェン環、又はアルキル置換若しくは無置換ベンゾフラン環を形成していてもよく；Ｒ_１２０～Ｒ_１２３は、隣接する置換基と連結して環を形成していてもよく、例えばＲ_１２０とＲ_１２１は、互いに連結して、アルキル－、アリール－、アラルキル－、及びアルキルアリール－置換若しくは無置換ベンゼン環のうちの少なくとも１つ、又は少なくとも１つのアルキル置換若しくは無置換フルオレン環、ジベンゾフラン環、又はジベンゾチオフェン環を形成していてもよく；
Ｒ_１２４～Ｒ_１２７は、それぞれ独立して、水素、重水素、ハロゲン、置換若しくは無置換（Ｃ１～Ｃ３０）アルキル、又は置換若しくは無置換（Ｃ６～Ｃ３０）アリールを表すか；又は隣接する置換基に連結して環、例えばアルキル置換若しくは無置換インデン環、アルキル置換若しくは無置換ベンゾチオフェン環、又はアルキル置換若しくは無置換ベンゾフラン環を形成していてもよく；
Ｒ_２０１～Ｒ_２１１は、それぞれ独立して、水素、重水素、ハロゲン、重水素－又はハロゲン－置換若しくは無置換（Ｃ１～Ｃ３０）アルキル、置換若しくは無置換（Ｃ３～Ｃ３０）シクロアルキル、又はアルキル－若しくは重水素－置換若しくは無置換（Ｃ６～Ｃ３０）アリールを表すか；又は隣接する置換基に連結して環、例えばアルキル置換若しくは無置換インデン環、アルキル置換若しくは無置換ベンゾチオフェン環、又はアルキル置換若しくは無置換ベンゾフラン環を形成していてもよく；
ｒはそれぞれ独立して１～３の整数を表し；ｒが２以上である場合には、各Ｒ_１００は同じであっても異なっていてもよく；
ｎは１～３の整数を表す）。 As the dopant, a compound represented by any one of the following formulas 101 to 103 can be used, but is not limited to these:

(wherein L is the following structure 1 or 2:

R ₁₀₀ each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30) cycloalkyl;
R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cyclo Represents alkyl, substituted or unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked with adjacent substituents to form a ring; Specific R ₁₀₆ to R ₁₀₉ are bonded to adjacent substituents to form a ring, such as an alkyl-substituted or unsubstituted indene ring, an alkyl-substituted or unsubstituted benzothiophene ring, or an alkyl-substituted or unsubstituted benzofuran ring. R ₁₂₀ to R ₁₂₃ may be linked to adjacent substituents to form a ring; for example, R ₁₂₀ and R ₁₂₁ may be linked to each other to form an alkyl-, aryl-, aralkyl-, and alkylaryl-at least one substituted or unsubstituted benzene ring, or at least one alkyl substituted or unsubstituted fluorene ring, dibenzofuran ring, or dibenzothiophene ring;
R ₁₂₄ to R ₁₂₇ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1 to C30) alkyl, or substituted or unsubstituted (C6 to C30) aryl; or an adjacent substituent may be linked to form a ring, such as an alkyl-substituted or unsubstituted indene ring, an alkyl-substituted or unsubstituted benzothiophene ring, or an alkyl-substituted or unsubstituted benzofuran ring;
R ₂₀₁ to R ₂₁₁ are each independently hydrogen, deuterium, halogen, deuterium- or halogen-substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, or alkyl - or deuterium - represents a substituted or unsubstituted (C6-C30) aryl; or linked to an adjacent substituent to form a ring, such as an alkyl-substituted or unsubstituted indene ring, an alkyl-substituted or unsubstituted benzothiophene ring, or an alkyl May form a substituted or unsubstituted benzofuran ring;
Each r independently represents an integer from 1 to 3; when r is 2 or more, each R ₁₀₀ may be the same or different;
n represents an integer from 1 to 3).

Specific examples of dopant compounds include, but are not limited to, the following:

The compound represented by formula 1 of the present disclosure can be used in at least one layer constituting an organic electroluminescent device, such as a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, an electron transport layer, an electron It may be included in at least one layer selected from a buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Furthermore, the compound represented by Formula 1 of the present disclosure may be included in the hole transport zone, preferably in the second hole transport layer of the hole transport zone, but is not limited thereto.

Organic electroluminescent materials, such as hole-injecting materials, hole-transporting materials, hole-assisting materials, luminescent-assisting materials, electron-blocking materials, luminescent materials, electron-buffering materials, hole-blocking materials, electron-transporting materials, and electron-injecting materials At least one of the materials can include a compound represented by Formula 1 above. The material may be a hole transport zone material. The hole transport zone material may consist solely of the organic electroluminescent compound represented by Formula 1, or may further include conventional materials included in organic electroluminescent materials.

Organic electroluminescent materials according to one embodiment can be used as light emitting materials for white organic light emitting devices. White organic light emitting devices can be manufactured using parallel arrangement method, stacked arrangement method or CCM (color conversion material) depending on the arrangement of R (red), G (green), B (blue) or YG (yellow green) light emitting units. Various structures such as laws have been proposed. In addition, organic electroluminescent materials according to one embodiment may also be applied to organic electroluminescent devices including QDs (quantum dots).

An organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer sandwiched between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode and the other may be a cathode. Here, the first electrode and the second electrode may each be formed as a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material. The organic electroluminescent device can be top-emitting, bottom-emitting or double-emitting depending on the type of material forming the first and second electrodes. The organic layer can include at least one emissive layer, including a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a It can further include at least one layer selected from a hole blocking layer and an electron blocking layer.

Organic electroluminescent devices according to the layers of the present disclosure can include an organic electroluminescent compound represented by Formula 1 above, and may also include conventional materials included in organic electroluminescent materials. . Organic electroluminescent devices comprising organic electroluminescent compounds represented by Formula 1 above can exhibit high luminous efficiency and/or long lifetime characteristics.

Further, the present disclosure can provide a display device by using the compound represented by Formula 1. That is, by using the compounds of the present disclosure, it is possible to manufacture display devices or lighting devices. Specifically, the organic electroluminescent compound of the present disclosure can be used for manufacturing display devices such as smartphones, tablets, notebooks, PCs, and TVs, or display devices for cars, or lighting devices such as outdoor or indoor lighting. It can be used for.

Hereinafter, in order to understand the present disclosure in detail, methods for preparing the compounds of the present disclosure and their properties will be described in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[Example 1] Preparation of compound C-123

1) Preparation of Compound 1-1 Compound A (37 g, 205.05 mmol), 2-bromo-6-chlorobenzaldehyde (30 g, 136.7 mmol), tetrakis(triphenylphosphine)palladium (4.7 g, 4.1 mmol) , potassium carbonate (47.2 g, 341.75 mmol), 400 mL of tetrahydrofuran, and 100 mL of distilled water were placed in a reaction vessel and stirred at 100° C. for 4 hours. After the reaction was completed, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it on a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain Compound 1-1 (35 g, yield: 94%).

2) Preparation of compound 1-2 In 350 mL of tetrahydrofuran, compound 1-1 (35 g, 128.32 mmol) and (methoxymethyl)triphenylphosphinium chloride (66 g, 192.48 mmol) were placed in a reaction vessel. . Then, 193 mL of potassium tert-butoxide (1M) was added dropwise to the mixture at 0°C. After the addition was complete, the reaction temperature was slowly raised to room temperature and the mixture was stirred for an additional 2 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the extracted organic layer was dried over magnesium sulfate. Thereafter, the solvent was removed from it using a rotary evaporator, and the remaining product was then purified by column chromatography to obtain Compound 1-2 (31 g, yield: 80%).

3) Preparation of Compound 1-3 After dissolving Compound 1-2 (31 g, 103.06 mmol) in chlorobenzene, 3.1 mL of Eaton's reagent was slowly dropped into the reaction vessel. After the addition was complete, the mixture was stirred for an additional 2 hours. After the reaction was completed, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it on a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain Compound 1-3 (24.4 g, yield: 88%).

4) Preparation of compound C-123 Compound 1-3 (3.5 g, 13.02 mmol), N,9-diphenyl-9H-carbazol-2-amine (4.8 g, 14.33 mmol), tris(dibenzylideneacetone) ) Dipalladium(0) (0.6 g, 0.65 mmol), tri-tert-butylphosphine (0.3 mL, 1.30 mmol), sodium tert-butoxide (1.9 g, 19.53 mmol), and 65 mL toluene. was placed in a reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; the solid was then filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-123 (6 g, yield: 81%).

化合物１－３（３．０ｇ、１１．１６ｍｍｏｌ）、Ｎ－（［１，１’－ビフェニル］－２－イル）－９－フェニル－９Ｈ－カルバゾール－２－アミン（５．０ｇ、１２．２８ｍｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラジウム（０）（０．５ｇ、０．５６ｍｍｏｌ）、トリ－ｔｅｒｔ－ブチルホスフィン（０．３ｍＬ、１．１２ｍｍｏｌ）、ナトリウムｔｅｒｔ－ブトキシド（１．６ｇ、１６．７４ｍｍｏｌ）、及び５６ｍＬのトルエンを反応容器に入れ、１時間還流した。反応混合物を室温に冷却し；次いで固体を濾過し、酢酸エチルで洗浄した。濾液を減圧下で蒸留し、カラムクロマトグラフィーにより精製することで、化合物Ｃ－１２４（２ｇ、収率：２８％）を得た。 [Example 2] Preparation of compound C-124

Compound 1-3 (3.0 g, 11.16 mmol), N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazol-2-amine (5.0 g, 12.28 mmol) ), tris(dibenzylideneacetone)dipalladium(0) (0.5 g, 0.56 mmol), tri-tert-butylphosphine (0.3 mL, 1.12 mmol), sodium tert-butoxide (1.6 g, 16. 74 mmol) and 56 mL of toluene were placed in a reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; the solid was then filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-124 (2 g, yield: 28%).

化合物１－３（３．５ｇ、１３．０２ｍｍｏｌ）、Ｎ－（［１，１’－ビフェニル］－２－イル）－９，９’－ジメチル－９Ｈ－フルオレン－２－アミン（５．２ｇ、１４．３３ｍｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラジウム（０）（０．６ｇ、０．６５ｍｍｏｌ）、トリ－ｔｅｒｔ－ブチルホスフィン（０．３ｍＬ、１．３０ｍｍｏｌ）、ナトリウムｔｅｒｔ－ブトキシド（１．９ｇ、１９．５３ｍｍｏｌ）、及び６５ｍＬのトルエンを反応容器に入れ、１時間還流した。反応混合物を室温に冷却し；次いで固体を濾過し、酢酸エチルで洗浄した。濾液を減圧下で蒸留し、カラムクロマトグラフィーにより精製することで、化合物Ｃ－１２５（１．３ｇ、収率：１７％）を得た。 [Example 3] Preparation of compound C-125

Compound 1-3 (3.5 g, 13.02 mmol), N-([1,1'-biphenyl]-2-yl)-9,9'-dimethyl-9H-fluoren-2-amine (5.2 g, 14.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.6 g, 0.65 mmol), tri-tert-butylphosphine (0.3 mL, 1.30 mmol), sodium tert-butoxide (1.9 g , 19.53 mmol) and 65 mL of toluene were placed in a reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; the solid was then filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-125 (1.3 g, yield: 17%).

In the following, properties of organic electroluminescent devices comprising the organic electroluminescent compounds of the present disclosure will be described for a detailed understanding of the present disclosure. However, the following description of the examples is intended to explain the characteristics of the OLED according to the present disclosure in order to understand the present disclosure in detail, and the present disclosure is meant to be limited to the following examples. It's not a thing.

[Device Examples 1-3] Fabrication of OLEDs Comprising Organic Electroluminescent Compounds According to the Present Disclosure OLEDs were fabricated using the organic electroluminescent compounds of the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω/sq), which is a transparent electrode of a glass substrate for OLED (Geomatec Co., Ltd., Japan), was sequentially ultrasonically cleaned with acetone and isopropanol, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum evaporation apparatus. Compound HI-1 was introduced into the cell of a vacuum evaporator and the pressure in the chamber of the apparatus was then controlled at 10 ^-6 Torr. Thereafter, a current was applied to the cell to evaporate the introduced substance, thereby forming a first hole injection layer with a thickness of 90 nm on the ITO substrate. Compound HI-2 is then introduced into another cell of the vacuum evaporator, and a current is passed through the cell to evaporate the introduced material, thereby forming a 5 nm thick layer on the first hole injection layer. A second hole injection layer was formed. Compound HT-1 was then introduced into another cell of the vacuum evaporator. Thereafter, a current was applied to the cell to evaporate the introduced substance, thereby forming a first hole transport zone with a thickness of 10 nm in the second hole injection layer. Next, the compound in Table 1 below (second hole transport material) is introduced into another cell of the vacuum evaporation apparatus, and a current is passed through the cell to evaporate the introduced substance, thereby forming the first hole transport material. A second hole transport band (auxiliary layer) having a thickness of 60 nm was formed on the hole transport band. After forming the hole injection layer and hole transport zone, the emissive layer was deposited as follows. Compound H-1 was introduced as a host into one cell of the vacuum evaporation apparatus, and compound D-71 was introduced as a dopant into another cell of the apparatus. The dopant was deposited at a doping amount of 2% by weight based on the total amount of host and dopant to form a 40 nm thick emissive layer on the hole transport layer. Compounds ET-1 and EI-1 were then introduced into another cell, evaporated and deposited in a 1:1 ratio to form an electron transport layer with a thickness of 35 nm on the emissive layer. Next, compound EI-1 was deposited on the electron transport layer as an electron injection layer with a thickness of 2 nm, and an Al cathode with a thickness of 1500 nm was deposited on the electron injection layer using another vacuum deposition apparatus, thereby manufacturing an OLED. .

[Comparative Examples 1 and 2] Manufacture of OLEDs using compounds not according to the present disclosure Device Examples 1-3 manufactured in the same manner as.

The compounds used in Device Examples 1 to 3 and Comparative Examples 1 and 2 are as follows.

The driving voltage, power efficiency, and CIE color coordinate results at a brightness of 1,000 nits for the OLED manufactured as described above are shown in Table 1 below.

Further, the time required for the luminance to decrease to 98% (lifetime; T98) at a constant current based on a luminance of 5,000 nits for Device Example 2 and Comparative Example 1 is 98 hours and 18 hours, respectively.

In the device examples and comparative examples above, organic electroluminescent devices comprising organic electroluminescent compounds of the present disclosure have lower driving voltages and/or It was confirmed that it has high power efficiency. Concomitantly or alternatively, organic electroluminescent devices comprising organic electroluminescent compounds of the present disclosure can have improved lifetime characteristics.

Claims (8)

An organic electroluminescent compound represented by the following formula 1:

(In the formula,
X represents O or S;
Ar ₁ to Ar ₄ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30) member) heteroaryl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1- C30) represents alkyl(C6-C30)arylamino, provided that Ar ₁ to Ar ₄ are

(In the formula, * is the bonding site to the nitrogen atom.)
Neither of ;
L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) C30) alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or substituted or unsubstituted (C1-C30) C30) represents alkyl (C6-C30) arylamino;
a represents an integer from 1 to 4, b represents an integer from 1 to 5, and when a and b are integers of 2 or more, each R ₁ and each R ₂ may be the same or different. Also good;
p and q each independently represent 0 or 1 on the condition that the sum of p and q is 1 or 2, and when the sum of p and q is 2, L ₁ and L ₂ , and Ar ₁ to Ar ₄ may be the same or different). The substituted (C1-C30) alkyl, the substituted (C6-C30) aryl (ene), the substituted (3-30 membered) heteroaryl (ene), the substituted (C3-C30) cycloalkyl, the substituted (C1-C30) C30) alkoxy, the above-mentioned substituted tri(C1-C30)alkylsilyl, the above-mentioned substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the above-mentioned substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the above-mentioned substitution tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6 ~C30) The above substituents of arylamino are each independently 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, (3-7 membered) heterocycloalkyl, (C6 ~C30) Aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-30 membered) heteroaryl, (3-30 membered) heteroaryl substituted or unsubstituted (C6-C30) aryl , tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, Mono- or di-(C1-C30) alkylamino, (C1-C30) alkyl-substituted or unsubstituted 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) A claim representing at least one member selected from the group consisting of alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. Item 1. The organic electroluminescent compound according to item 1. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 4:

(In the formula,
p and q each independently represent 0 or 1, and the sum of p and q is 1;
X, Ar ₁ to Ar ₄ , L ₁ , L ₂ , R ₁ , R ₂ , a, and b are as defined in claim 1). Ar ₁ to Ar ₄ each independently represent substituted or unsubstituted (C1 to C20) alkyl, substituted or unsubstituted (C6 to C25) aryl, substituted or unsubstituted (3 to 25 membered) heteroaryl, substituted or unsubstituted (C6 to C25) heteroaryl, substituted mono- or di-(C1-C20) alkylamino, substituted or unsubstituted mono- or di-(C6-C25) arylamino, or substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylamino Representation;
L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C6-C 25 ) arylene, or substituted or unsubstituted (3-25 membered) heteroarylene;
R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C20) alkyl, substituted or unsubstituted (C6 to C25) aryl, or substituted or unsubstituted (3 ~25-membered) represents a heteroaryl;
p and q each independently represent 0 or 1 on the condition that the sum of p and q is 1;
An organic electroluminescent compound according to claim 1. The organic electroluminescent compound of claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:

An organic electroluminescent material comprising an organic electroluminescent compound according to claim 1. An organic electroluminescent device comprising an organic electroluminescent compound according to claim 1. 8. The organic electroluminescent device of claim 7, wherein the organic electroluminescent compound is included in a hole transport zone.