JP2021529774A - Organic electroluminescent compounds and organic electroluminescent devices containing them - Google Patents

Abstract

The present disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device containing the same. By including the organic electroluminescent compound according to the present disclosure, it is possible to provide an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and a long life as compared with a conventional organic electroluminescent device. .. [Selection diagram] None

Description

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

_{The green-emitting TPD / Alq 3} bilayer small molecule organic electroluminescent device, which consists of a light emitting layer and a charge transport layer, was first developed in 1987 by Tang et al. Of Eastman Kodak. Since then, research on organic electroluminescent devices has been rapidly commercialized. An organic electroluminescent device (OLED) converts electrical energy into light by applying electricity to an organic electroluminescent material and typically includes an anode, a cathode, and an organic layer formed between two electrodes. The organic electroluminescent device has a multi-layer structure including a hole transport band, a light emitting layer, an electron transport band, and the like in order to improve its efficiency and stability.

Furthermore, since the performance of an organic electroluminescent device largely depends on the compound contained in each band or layer, research on a new compound capable of improving the performance of the organic electroluminescent device has been actively conducted. 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 was used as a compound contained in the hole transport zone in organic electroluminescent devices. However, organic electroluminescent devices using these materials have problems of reduced luminous efficiency and life. This is because when an organic electroluminescent device is driven under high current, thermal stress is created between the anode and the hole injection layer, which significantly reduces the life of the device. .. Further, since the organic material used in the hole transport zone has a very high hole mobility, there is a problem that the charge balance between holes and electrons is lost and the quantum efficiency (cd / A) is lowered. .. Therefore, there is a need for new compounds that can replace conventional compounds used in the hole transport zone. In addition, studies have been conducted on various materials and devices to improve the luminous efficiency, drive voltage, and / or lifetime characteristics of organic electroluminescent devices.

Korean Patent Application Publication No. 2017-090670A discloses a compound in which an amine is bound to a specific position of benzonaphthophene or benzonaphthofuran as a compound contained in a hole transport layer of an organic electroluminescent device. I'm just doing it.

An object of the present disclosure is to provide an organic electroluminescent compound that is effective for producing organic electroluminescent devices having low drive voltage and / or high luminous efficiency and / or long life.

The present inventors have reduced the degree of free rotation due to steric hindrance of the molecule without significantly changing the triplet energy, as compared with the compounds disclosed in Publication No. 2017-090670A of the Korean Patent Application. It has been found that the above-mentioned object can be achieved and the present invention can be completed by the organic electroluminescent compound represented by the following formula 1 which enhances the rigidity of the molecule.

In Equation 1,
X represents O or S;
Ar _{1 to} Ar ₄ are independently hydrogen, dehydrogen, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30), respectively. 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) C30) Alkyl (C6-C30) represents 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 independently represent single-bonded, substituted or unsubstituted (C6 to C30) arylene, or substituted or unsubstituted (3 to 30 member) heteroarylene;
R ₁ and R ₂ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 3 to C30), respectively. 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 to C30) arylsilyls, substituted or unsubstituted (C1 to C30) alkyldi (C6 to C30) arylsilyls, substituted or unsubstituted tri (C6 to C30) arylsilyls, or substituted or unsubstituted (C1 to C1). C30) Represents alkyl (C6-C30) arylamino;
a represents an integer of 1 to 4, b represents an integer of 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 independently represent 0 or 1, provided that the sum of p and q is 1 or 2, respectively, 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 The organic electroluminescent compounds according to the present disclosure can provide organic electroluminescent devices with low drive voltage, high luminous efficiency, and / or long life.

This disclosure will be described in detail below. However, the following description is intended to illustrate the invention and by no means limits the scope of the invention.

The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if desired, contained in any material layer constituting the organic electroluminescent device.

The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can optionally be included in any layer constituting the organic electroluminescent device. For example, an organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transporting material, or an electron. It can be an injection material or the like.

The term "hole transport zone" means the band in which holes move between the first electrode and the light emitting layer. For example, the hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the light emission auxiliary layer, and the electron blocking layer may each be a single layer, or may be a multi-layer in which two or more layers are laminated. 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 auxiliary layer, a light emitting auxiliary layer, and / or an electron blocking layer. Furthermore, 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 can be arranged between the first electrode and the light emitting layer, and the second hole transport layer can be arranged between the first hole transport layer and the light emitting layer. .. The second hole transport layer may serve as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

The hole transport layer may be arranged between the anode (or hole injection layer) and the light emitting layer, and smoothly moves the holes transferred from the anode to the light emitting layer, and the electrons transmitted from the cathode. Can function to block and retain in the light emitting layer. The light emitting auxiliary layer may be arranged between the anode and the light emitting layer, or between the cathode and the light emitting layer. When the emission auxiliary layer is placed between the anode and the emission layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the luminescent auxiliary layer is placed between the cathode and the luminescent 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 arranged between the hole transport layer (or hole injection layer) and the light emitting layer, and is effective in promoting or blocking the hole transport rate (or hole injection rate). It allows the charge balance to be controlled.

Further, the electron blocking layer can be arranged between the hole transporting layer (or the hole injection layer) and the light emitting layer, and the excitons are confined in the light emitting layer by blocking the overflow of electrons from the light emitting layer. It is possible to prevent light emission leakage. When the organic electroluminescent device contains two or more hole transport layers, the further included hole transport layers can be used as a light emitting auxiliary layer, a hole auxiliary layer, an electron blocking layer, and the like. The light emitting auxiliary layer, the hole auxiliary layer, and / or the electron blocking layer may have the effect of improving the luminous efficiency and / or the lifetime of the organic electroluminescent device.

As used herein, "(C1 to C30) alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is defined as. 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 to C30) alkenyl" is a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, and the number of carbon atoms is preferably 2 to 20, more preferably 2 to 20. The number is 10, and examples thereof include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "(C2 to C30) alkynyl" is a linear 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 20. The number is 10, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methylpent-2-ynyl. "(C3 to C30) cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 ring-skeleton carbon atoms, and the number of carbon atoms is preferably 3 to 20, more preferably. Is 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. A "(3-7 member) heterocycloalkyl" comprises at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N3. 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, tetrahydropyran and the like. "(C6 to C30) aryl (ene)" is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and the number of ring skeleton carbon atoms is The number is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated or may contain a spiro structure. Examples of aryls include, specifically, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo. Fluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthrasenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, perylenel, chrysenyl, benzocrisenyl, Examples thereof include naphthacenyl, fluoranthenyl, benzofluoranthenyl, trill, xylyl, mesityl, cumenyl, spiro [fluorene-fluorene] yl, spiro [fluorene-benzofluoren] yl, azlenyl and the like. More specifically, the aryls are o-tolyl, m-tolyl, p-tolyl, 2,3-kisilyl, 3,4-kisilyl, 2,5-kisilyl, mesityl, o-cumenyl, m-cumenyl, p. -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-anthril, 2-anthril, 9-anthril, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl , 4-Phenantril, 9-Phenantril, 1-Crycenyl, 2-Crysenyl, 3-Crycenyl, 4-Crycenyl, 5-Crysenyl, 6-Crysenyl, benzo [c] phenanthryl, benzo [g] Clycenyl, 1-triphenylenyl, 2 It may be −triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl and the like.

As used herein, the "(3 to 30 member) heteroaryl (en)" is at least one selected from the group consisting of B, N, O, S, Si, P, and Ge, preferably 1 to 4. It is an aryl having 3 to 30 ring skeleton atoms including 1 hetero atom, and the number of ring skeleton atoms is preferably 5 to 25. The heteroaryl may be a monocyclic ring or a condensed ring fused with at least one benzene ring; or may be partially saturated. The hetero atom is hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (5 to 30 member) hetero. Aryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri (C1 to C30) alkylsilyl, substituted or unsubstituted di (C1 to C1). C30) Alkoxy (C6-C30) arylsilyls, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyls, substituted or unsubstituted tri (C6-C30) arylsilyls, substituted or unsubstituted mono. -Or from di- (C1-C30) alkylaminos, substituted or unsubstituted mono- or di- (C6-C30) arylaminos, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylaminos. It may be linked to at least one substituent selected from the group. Further, the heteroaryl may be formed by attaching at least one heteroaryl or aryl group to the heteroaryl group via a single bond; and may also contain a spiro structure. Specific examples of heteroaryls include frills, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, frazayl, pyridyl, pyrazinyl, pyrimidinyl, Monocyclic heteroaryls such as pyridazinyl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, Imidazopyridinyl, isoindryl, indolyl, benzoindolyl, indazolyl, benzothiasiazolyl, quinolyl, isoquinolyl, synnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxadinyl, phenanthridinyl, Condensed ring-type heteroaryls such as benzodioxolyl, indolidinyl, acryridinyl, silafluorenyl, and germanefluorenyl can be mentioned. More specifically, the heteroaryls are 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1- Indridinyl, 2-Indridinyl, 3-Indridinyl, 5-Indridinyl, 6-Indridinyl, 7-Indridinyl, 8-Indridinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazo Pyrizinyl, 7-imidazolipyridinyl, 8-imidazolipyridinyl, 1-indrill, 2-indrill, 3-indrill, 4-indrill, 5-indrill, 6-indrill, 7-indrill, 1-isoindrill, 2-Isoindrill, 3-Isoindrill, 4-Isoindrill, 5-Isoindrill, 6-Isoindrill, 7-Isoindrill, 2-Frill, 3-Frill, 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- Mequinolyl, 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, azacarbazole-1-yl, azacarbazole-2-yl, Azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1 -Phenantridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9- Phenantrigi Nyl, 10-phenanthridinyl, 1-acridinyl, 2-acrydinyl, 3-acridinyl, 4-acrydinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3 -Frazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methyl Pyrrole-1-yl, 3-Methylpyrol-2-yl, 3-Methylpyrol-4-yl, 3-Methylpyrol-5-yl, 2-t-butylpyrol-4-yl, 3- (2-phenylpropi) Le) Pyrrole-1-yl, 2-methyl-1-indrill, 4-methyl-1-indrill, 2-methyl-3-indrill, 4-methyl-3-indrill, 2-t-butyl-1-indrill, 4-t-butyl-1-indrill, 2-t-butyl-3-indrill, 4-t-butyl-3-indrill, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4- Dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluolenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl , 2-Germafluorenyl, 3-Germafluolenyl, 4-Germafluolenyl and the like. "Halogen" includes F, Cl, Br, and I.

In the present specification, "ortho (o)", "meta (m)" and "para (p)" mean that the substitution positions of all substituents are indicated. The ortho position is, for example, a compound having substituents adjacent to each other at the 1- and 2-positions of benzene. The meta position is the substitution position next to the substitution position directly adjacent to each other, and is, for example, a compound having a substituent at the 1st and 3rd positions of benzene. The para position is the substitution position next to the meta position, and is, for example, a compound having a substituent at the 1st and 4th positions of benzene.

Furthermore, "substitution" in the expression "substituent or unsubstituted" means that a hydrogen atom in a particular functional group has been replaced by another atom or another functional group, i.e., a substituent. Substituted (C1-C30) alkyl, substituted (C6-C30) aryl (ene), substituted (3-30 member) heteroaryl (ene), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted Tri (C1-C30) alkylsilyls, substituted di (C1-C30) alkyl (C6-C30) arylsilyls, substituted (C1-C30) alkyldi (C6-C30) arylsilyls, substituted tri (C6-C30) arylsilyls, Substituents of substituted mono- or di- (C1-C30) alkylaminos, substituted mono- or di- (C6-C30) arylaminos, and substituted (C1-C30) alkyl (C6-C30) arylaminos are independent of each other. Then, heavy hydrogen, halogen, cyano, carboxyl, nitro, hydroxy, (C1 to C30) alkyl, halo (C1 to C30) alkyl, (C2 to C30) alkenyl, (C2 to C30) alkynyl, (C1 to C30). Alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6 to C30) aryl substituted or unsubstituted (3 to 30 member) heteroaryl, (3 to 30 member) heteroaryl substituted or unsubstituted (C6 to C30) aryl, tri (C1 to 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 at least one selected from the group. According to one embodiment, the substituents independently represent (C1-C20) alkyl and / or (C6-C25) aryl, respectively. According to another embodiment, the substituents independently represent at least one of (C1-C10) alkyl and (C6-C18) aryl. For example, the substituents may be at least one of methyl, phenyl, naphthyl, and biphenyl, each independently.

As used herein, the term "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 Means these combinations and is formed by linking or condensing two or more adjacent substituents; preferably substituted or unsubstituted (3-26 member) monocyclic or polycyclic aliphatic rings. , Aromatic rings, or a combination thereof. Furthermore, the formed ring 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, Si P, and Ge. You may be. Further, the hetero atom is hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 member) heteroaryl. , Substituent or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri (C1 to C30) alkylsilyl, substituted or unsubstituted di (C1 to 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-C1 At least selected from the group consisting of C30) alkylaminos, substituted or unsubstituted mono- or di- (C6-C30) arylaminos, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylaminos. It may be linked to one substituent.

The compound represented by the formula 1 can be represented by any one of the following formulas 2 to 4.

In Equations 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 Equation 1. According to one embodiment, the sum of p and q may be 1.

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

In formulas 1 to 4, Ar _{1 to} Ar ₄ are independently hydrogen, dehydrogen, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted. Substituted (3-30 member) heteroaryl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or Represents an unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or Ar ₁ and Ar ₂ may be linked to each other to form a ring, and Ar ₃ and Ar ₄ may be linked to each other. It may form a ring. According to one embodiment, Ar _{1 to Ar 4} are independently hydrogen, dehydrogen, substituted or unsubstituted (C1 to C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted. (3-25 members) 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) Alkyl (C6-C25) represents arylamino. According to another embodiment, Ar _{1 to Ar 4} are independently substituted or unsubstituted (C1 to C10) alkyl, substituted or unsubstituted (C6 to C25) aryl, or substituted or unsubstituted (5 to 5). 25 members) Represents heteroaryl. For example, Ar _{1 to} Ar ₄ independently contain unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted phenanthrenyl, unsubstituted naphthylphenyl, phenyl substituted or unsubstituted dimethylfluorenyl, and unsubstituted diphenylfluore. It may be enyl, 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 be independently selected from the following groups, respectively. For example, when Ar ₁ is phenyl, Ar ₂ may be any one of the following compounds.

In Formulas 1-4, L ₁ and L ₂ independently represent single-bonded, substituted or unsubstituted (C6 to C30) arylene, or substituted or unsubstituted (3 to 30 member) heteroarylene; one embodiment. According to the morphology, L ₁ and L ₂ independently represent single-bonded, substituted or unsubstituted (C6 to C25) arylene, or substituted or unsubstituted (3 to 25 member) heteroarylene; another embodiment. According to the morphology, L ₁ and L ₂ independently represent single-bonded, unsubstituted (C6-C18) arylene, or unsubstituted (3-18-membered) heteroarylene, respectively. For example, L ₁ and L ₂ may be single-bonded, unsubstituted phenylene, or unsubstituted naphthylene, respectively.

In formulas 1 to 4, R ₁ and R ₂ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted, respectively. Alternatively, unsubstituted (3 to 30 member) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri (C1 to 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, or substituted. or unsubstituted (C1-C30) alkyl (C6 to C30) aryl amino; According to one embodiment, _{R 1} and _{R 2} are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted Represents substituted (C1 to C20) alkyl, substituted or unsubstituted (C6 to C25) aryl, or substituted or unsubstituted (3 to 25 member) heteroaryl; according to another embodiment, R ₁ and R ₂ are. Each independently represents hydrogen, dehydrogen, halogen, cyano, unsubstituted (C1 to C10) alkyl, unsubstituted (C6 to C25) aryl, or substituted or unsubstituted (5 to 25 member) heteroaryl. For example, R ₁ and R ₂ can be hydrogen.

In equations 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 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 Equations 1 to 4, p and q independently represent 0 or 1, provided that the sum of p and q is 1 or 2, respectively, 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, and if p is 1, q is 0.

The compounds represented by the formula 1 can be more specifically represented by the following compounds, but are not limited thereto.

The organic electroluminescent compound of the present disclosure can be produced by a synthetic method known to those skilled in the art. For example, the organic electroluminescent compounds of the present disclosure can be synthesized as represented by the following reaction schemes 1-3, but are not limited thereto.

[Reaction scheme 1]

[Reaction scheme 2]

[Reaction scheme 3]

In the 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 synthetic examples of the compounds represented by formulas 2-4 according to one embodiment are described, but they are the Buckwald-Hartwig cross-coupling reaction, the Wittich reaction, the Ulmann coupling reaction. , Suzuki cross-coupling reaction, N-aryllation reaction, H-mont-mediated etherification reaction, Miyaura boronization reaction, intramolecular acid-induced cyclization reaction, Pd (II) -catalyzed oxidation cyclization reaction, Grinard reaction, Heck reaction, It is based on a cyclic dehydration reaction, an SN ₁ substitution reaction, an SN ₂ substitution reaction, a phosphine-mediated reduction cyclization reaction, and the like. It will be appreciated by those skilled in the art that the above reaction will proceed even when other substituents defined in Formulas 2-4 other than the substituents described in the specific synthetic examples are attached. ..

The dopant 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 not limited to these, but is a metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably iridium (Ir). , Osmium (Os), copper (Cu), and platinum (Pt) can be an orthometallized complex compound of metal atoms, even more preferably an orthometallized 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 the dopant is not limited to these:

(In the formula, L is the following structure 1 or 2:

Is selected _{from, R 100} represents each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or a substituted or unsubstituted a (C3 to C30) cycloalkyl;
R _{101 to} R ₁₀₉ and R _{111 to} R ₁₂₃ are independently hydrogen, dehydrogen, halogen, dehydrogen 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 to adjacent substituents to form a ring; specifically. R _{106 to} R ₁₀₉ are attached to adjacent substituents to form a ring, such as an alkyl-substituted or unsubstituted inden 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 at least one of the alkylaryl-substituted or unsubstituted benzene rings, or at least one alkyl-substituted or unsubstituted fluorene ring, dibenzofuran ring, or dibenzothiophene ring may be formed;
R _124- R ₁₂₇ independently represent hydrogen, dehydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; or adjacent substituents. It may be linked to to form a ring, such as an alkyl-substituted or unsubstituted inden ring, an alkyl-substituted or unsubstituted benzothiophene ring, or an alkyl-substituted or unsubstituted benzofuran ring;
R _{201 to} R ₂₁₁ are independently hydrogen, dehydrogen, halogen, dehydrogen- or halogen-substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, or alkyl. -Or dehydrogen-representing a substituted or unsubstituted (C6-C30) aryl; or a ring linked to an adjacent substituent, such as an alkyl-substituted or unsubstituted inden ring, an alkyl-substituted or unsubstituted benzothiophene ring, or an alkyl. It may form a substituted or unsubstituted benzofuran ring;
r independently represent an integer of 1-3; if r is 2 or greater, 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 compound represented by the formula 1 of the present disclosure includes at least one layer constituting the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, and an electron. It may be contained 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. Further, the compound represented by the formula 1 of the present disclosure may be contained in the second hole transport layer of the hole transport zone, preferably the hole transport zone, but is not limited thereto.

Organic electroluminescent materials such as hole injection materials, hole transport materials, hole auxiliary materials, light emission auxiliary materials, electron blocking materials, light emitting materials, electron buffering materials, hole blocking materials, electron transport materials, and electron injection materials. At least one of the materials can include a compound represented by the above formula 1. The material may be a hole transport zone material. The hole transport zone material may be composed only of the organic electroluminescent compound represented by the formula 1, or may further contain a conventional material contained in the organic electroluminescent material.

The organic electroluminescent material according to one embodiment can be used as a light emitting material for a white organic light emitting device. The white organic light emitting device is a parallel parallel arrangement method, a laminated arrangement method, or a CCM (color conversion material) depending on the arrangement of R (red), G (green), B (blue), or YG (yellowish green) light emitting units. Various structures such as law have been proposed. In addition, the organic electroluminescent material according to one embodiment may also be applied to organic electroluminescent devices containing QDs (quantum dots).

The 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 can be an anode and the other can be a cathode. Here, the first electrode and the second electrode can be formed as a permeable conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. The organic electroluminescent device can be top-emission, bottom-emission or double-sided, depending on the type of material forming the first and second electrodes. The organic layer can include at least one light emitting layer, which includes a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, and a positive layer. It may further include a hole blocking layer and at least one layer selected from an electron blocking layer.

The organic electroluminescent device according to the layers of the present disclosure can contain the organic electroluminescent compound represented by the above formula 1, and may further contain conventional materials contained in the organic electroluminescent material. .. An organic electroluminescent device containing an organic electroluminescent compound represented by the above formula 1 can exhibit high luminous efficiency and / or long life characteristics.

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

In the following, in order to understand the present disclosure in detail, the preparation methods of the compounds of the present disclosure and their properties will be described in detail with reference to the 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 completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, from which the solvent was removed with a rotary evaporator. The remaining product was then purified by column chromatography to give 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) triphenylphosphine chloride 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 dropping was complete, the reaction temperature was slowly raised to room temperature and the mixture was stirred for an additional 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the extracted organic layer was dried over magnesium sulfate. The solvent was then removed from it with a rotary evaporator and then the remaining product was purified by column chromatography to give 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 added dropwise to the reaction vessel. After the dropping was complete, the mixture was stirred for an additional 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, from which the solvent was removed with a rotary evaporator. The remaining product was then purified by column chromatography to give 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-carbazole-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; then the solid was 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-carbazole-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 the reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; then the solid was 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 the reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; then the solid was 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, in order to understand the present disclosure in detail, the characteristics of the organic electroluminescent device containing the organic electroluminescent compound of the present disclosure will be described. However, the description of the following 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 to 3] Production of an OLED containing an organic electroluminescent compound according to the present disclosure An OLED was produced using the organic electroluminescent compound of the present disclosure. First, an indium tin oxide (ITO) thin film (10Ω / sq), which is a transparent electrode of a glass substrate for OLED (Geomatec Co., Ltd., Japan), was ultrasonically cleaned with acetone and isopropanol, and then stored in isopropanol. Next, the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition apparatus. Compound HI-1 was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to ^{10-6 tolls.} Then, an electric current was passed through the cell to evaporate the introduced substance, 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 deposition apparatus and an electric current was passed through the cell to evaporate the introduced material, thereby making a 5 nm thick first hole injection layer. A hole injection layer of 2 was formed. The compound HT-1 was then introduced into another cell of the vacuum deposition apparatus. Then, an electric current was passed through the cell to evaporate the introduced substance, thereby forming a first hole transport zone having a thickness of 10 nm in the second hole injection layer. The compounds in Table 1 below (second hole transport material) were then introduced into another cell of the vacuum vapor deposition apparatus and an electric current was passed through the cell to evaporate the introduced material, thereby causing the first. A second hole transport zone (auxiliary layer) having a thickness of 60 nm was formed on the hole transport zone. After forming the hole injection layer and the hole transport zone, the light emitting layer was vapor-deposited as follows. Compound H-1 was introduced into one cell of the vacuum deposition apparatus as a host and compound D-71 was introduced into another cell of the apparatus as a dopant. The dopant was deposited with a doping amount of 2% by weight based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 40 nm on the hole transport layer. Next, the compounds ET-1 and EI-1 were introduced into another cell, evaporated at a ratio of 1: 1 and vapor-deposited to form an electron transport layer having a thickness of 35 nm on the light emitting layer. Next, compound EI-1 was deposited on the electron transport layer as an electron injection layer having a thickness of 2 nm, and an Al cathode having a thickness of 1500 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus, thereby producing an OLED. ..

[Comparative Examples 1 and 2] Production of OLED using a compound not according to the present disclosure OLED is used in Device Examples 1 to 3 except that the compound in Table 1 below is used in the second hole transport zone. Manufactured in the same way as.

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

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

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

In the device examples and comparative examples above, an organic electroluminescent device containing an organic electroluminescent compound of the present disclosure has a lower drive voltage and / or a lower drive voltage and / or compared to an organic electroluminescent device containing no compound of the present disclosure. It was confirmed that it has high power efficiency. At the same time or optionally, the organic electroluminescent device containing the organic electroluminescent compounds of the present disclosure can have improved life characteristics.

Claims (8)

Organic electroluminescent compound represented by the following formula 1:

(During the ceremony,
X represents O or S;
Ar _{1 to} Ar ₄ are independently hydrogen, dehydrogen, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30), respectively. 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) C30) Alkyl (C6 to C30) may represent 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 independently represent single-bonded, substituted or unsubstituted (C6 to C30) arylene or substituted or unsubstituted (3 to 30 member) heteroarylene;
R ₁ and R ₂ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 3 to C30), respectively. 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 to C30) arylsilyls, substituted or unsubstituted (C1 to C30) alkyldi (C6 to C30) arylsilyls, substituted or unsubstituted tri (C6 to C30) arylsilyls, or substituted or unsubstituted (C1 to C1). C30) Represents alkyl (C6-C30) arylamino;
a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are integers of 2 or more, each R ₁ and each R ₂ are the same but different. Also well;
p and q independently represent 0 or 1, provided that the sum of p and q is 1 or 2, respectively, 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 Substitution (C1-C30) Alkyl, The Substitution (C6-C30) Aryl (En), The Substitution (3-30 Members) Heteroaryl (En), The Substitution (C3-C30) Cycloalkyl, The Substitution (C1-C30) C30) alkoxy, said substituted tri (C1 to C30) alkylsilyls, said substituted di (C1 to C30) alkyl (C6 to C30) arylsilyls, said substituted (C1 to C30) alkyldi (C6 to C30) arylsilyls, said substitutions. Tri (C6-C30) arylsilyls, the substituted mono- or di- (C1-C30) alkylaminos, the substituted mono- or di- (C6-C30) arylaminos, and the substituted (C1-C30) alkyl (C6). ~ C30) The substituents of arylamino are independent of dehydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl. , (C2 to C30) alkynyl, (C1 to C30) alkoxy, (C1 to C30) alkylthio, (C3 to C30) cycloalkyl, (C3 to C30) cycloalkenyl, (3 to 7 member) heterocycloalkyl, (C6) ~ C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-30 member) heteroaryl, (3-30 member) heteroaryl substituted or unsubstituted (C6-C30) aryl , Tri (C1-C30) alkylsilyls, tri (C6-C30) arylsilyls, di (C1-C30) alkyl (C6-C30) arylsilyls, (C1-C30) alkyldi (C6-C30) arylsilyls, 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) Claimed to represent at least one selected from the group consisting of alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl. Item 2. 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.

(During the ceremony,
p and q 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 specified in claim 1). Ar _{1 to} Ar ₄ are independently substituted or unsubstituted (C1 to C20) alkyl, substituted or unsubstituted (C6 to C25) aryl, substituted or unsubstituted (3 to 25 member) heteroaryl, substituted or unsubstituted. Substituted mono- or di- (C1-C20) alkylaminos, substituted or unsubstituted mono- or di- (C6-C25) arylaminos, or substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylaminos. Representation;
L ₁ and _{L 2} are each independently a single bond, a substituted or unsubstituted (C6 to C30) arylene or a substituted or unsubstituted (3-25 membered) represents a heteroarylene;
R ₁ and R ₂ are 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 members) Represents heteroaryl;
p and q independently represent 0 or 1, provided that the sum of p and q is 1.
The organic electroluminescent compound according to claim 1. The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula 1 is selected from the group consisting of the following.

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