Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics and / or power efficiency can be provided.

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Art

[0002] An electroluminescent (EL) device is a self-luminous device having the advantages that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. Organic EL devices were first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] The most important factor determining the luminous efficiency in an organic electroluminescent device is the luminescent material. So far, fluorescent materials have been widely used as luminescent materials. However, in view of the electroluminescent mechanism, since phosphorescent luminescent materials theoretically enhance the luminous efficiency by four (4) times compared to fluorescent luminescent materials, phosphorescent luminescent materials have been widely studied. Iridium (III) complexes are widely known as phosphorescent luminescent materials, including bis(2-(2′-benzothienyl)-pyridine-N, C-3′)(acetylacetone)iridium ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(4,6-difluorophenylpyridine-N, C2)picolinyliridium (Firpic), which are red, green, and blue luminescent materials, respectively.

[0004] At present, 4,4′-N,N′-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, Pioneer Electronics (Japan) and others have developed a high-performance organic electroluminescent device using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq), which are known as hole blocking materials, as host materials.

[0005] Although these materials provide good luminescent characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during the high-temperature deposition process in a vacuum and the life of the device is reduced. (2) The power efficiency of an organic electroluminescent device is given by [(π / voltage)×current efficiency], and the power efficiency is inversely proportional to the voltage. Although an organic electroluminescent device containing a phosphorescent host material provides a higher current efficiency (cd / A) than an organic electroluminescent device containing a fluorescent material, a relatively high driving voltage is required. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) Furthermore, when these materials are used in an organic electroluminescent device, the operating life of the organic electroluminescent device is short and the luminescent efficiency still needs to be improved.

[0006] Various materials or concepts for organic layers of organic electroluminescent devices have been proposed in order to enhance luminous efficiency, driving voltage and / or lifespan, but they are not satisfactory in practical use. Summary of the invention

[0007] Technical issues

[0008] The object of the present disclosure is, first, to provide an organic electroluminescent compound for effectively producing an organic electroluminescent device with improved driving voltage, luminous efficiency, lifespan characteristics and / or power efficiency, and second, to provide an organic electroluminescent device comprising the organic electroluminescent compound.

[0009] Solution to the problem

[0010] The present disclosure solves the above problems by providing novel azabenzoazulene and derivatives of similar moieties and organic electroluminescent devices using the same. The introduction of aza-type moieties into HOMO molecules leads to the bipolar properties of HOMO molecules. It is related to the intermolecular or intramolecular flow of holes and electrons, which affects the bonding force of holes and electrons and the formation of excitons.

[0011] Meanwhile, compounds with low glass transition temperature (Tg) may reduce charge mobility in the film and degrade the performance of the OLED device. Although the structure of the present disclosure has a low molecular weight, it has a high glass transition temperature and can have excellent morphological stability. In addition, the structure of the present disclosure has a main core in a planar shape to facilitate π-π stacking in the vacuum deposited layer, which leads to fast charge mobility.

[0012] Specifically, the inventors of the present invention have found that the above-mentioned object can be achieved by an organic electroluminescent compound represented by the following formula 1:

[0013]

[0014] in

[0015] X1 represents -N(L1)(R5)-, -O-, -S- or -C(R6)(R7)-;

[0016] Y1 represents -N=, -N(R8)-, -O-, -S-, -C(R9)= or -C(R 10 )(R 11 )-;

[0017] Y2 represents -N- or -C=;

[0018] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, a substituted or unsubstituted (3- to 30-membered)heteroarylene group, or a substituted or unsubstituted (C3-C30)cycloalkylene group;

[0019] R1 to R3 and R6 to R 11 Each independently represents hydrogen, tritium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-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) alkyl(C6-C30) aryl or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be linked to an adjacent substituent to form a ring;

[0020] R4 and R5 each independently represent a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; and

[0021] a represents an integer of 1 or 2; b represents an integer of 1 to 3; c represents an integer of 1 to 4; wherein if a to c are each independently an integer of 2 or more, each of R1, each of R2 and each of R3 may be the same or different.

[0022] Beneficial effects of the present invention

[0023] By using the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having comparable or superior performance in driving voltage, high luminous efficiency, excellent lifespan characteristics, and / or high power efficiency may be produced. DETAILED DESCRIPTION

[0024] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0025] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as necessary.

[0026] 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. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0027] The organic electroluminescent material of the present disclosure may include at least one compound represented by Formula 1. The compound represented by Formula 1 may be included in a light-emitting layer, an electron transport layer and / or an electron buffer layer, but is not limited thereto. When included in the light-emitting layer, the compound represented by Formula 1 may be included as a host material. In this article, the host material may be a host material of an organic electroluminescent device emitting green or red light. In addition, when included in an electron transport layer, the compound represented by Formula 1 may be included as an electron transport material. In addition, when included in an electron buffer layer, the compound represented by Formula 1 may be included as an electron buffer material.

[0028] Herein, the term "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above-mentioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. The term "(C2-C30) alkenyl" means a straight or branched alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30) alkynyl" means a straight or branched alkynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term "(C3-C30) (sub) cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7, preferably 5 to 7 ring skeleton atoms and containing at least one heteroatom, the heteroatom being selected from the group consisting of B, N, O, S, Si and P, and preferably the group consisting of O, S and N. The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term "(C6-C30) (sub)aryl" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18. The above-mentioned aryl group may be partially saturated and may contain a spiro structure. The above-mentioned aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthyl, perylene, The aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacenyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] yl, 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, 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, and the like.

[0029] Herein, the term "(3-membered to 30-membered) (sub)heteroaryl" refers to an aryl group having 3 to 30 ring skeleton atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si and P. The above heteroaryl group may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and may contain a helical structure. The above heteroaryl groups may include monocyclic heteroaryl groups, such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and condensed ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzo imidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. More specifically, the heteroaryl group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 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-indolyl, 2- indolyl, 3-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 8-indolyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 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, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2- phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 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-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 2-methylpyrrol-6-yl, 2-methylpyrrol-7-yl, 2-methylpyrrol-8-yl, 2-methylpyrrol-9-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-1-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-2-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-1-yl, 2-methyl 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-tert-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 "Halogen" includes F, Cl, Br and I.

[0030] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. Ortho means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta means that two substituents are at positions 1 and 3, and for example, two substituents in a benzene derivative occupy positions 1 and 3, which is called meta. Para means that two substituents are at positions 1 and 4, and for example, two substituents in a benzene derivative occupy positions 1 and 4, which is called para.

[0031] In this document, the term "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (ie, a substituent). 11In the above, substituted (C1-C30) alkyl, substituted (C6-C30) (ene) aryl, substituted (3- to 30-membered) (ene) heteroaryl, substituted (C3-C30) (ene) 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, substituted mono- or di- (C1-C30) The substituents of the alkylamino, substituted mono- or di-(C6-C30)arylamino and substituted (C1-C30)alkyl(C6-C30)arylamino groups are each independently at least one selected from the group consisting of: tritium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocyclic alkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (5- to 30-membered) heteroaryl, unsubstituted or substituted by (C6-C30) aryl; (C6-C30) aryl, unsubstituted or substituted by (5- to 30-membered) heteroaryl; 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; substituted or substituted by (C1-C30) alkyl mono- or di-(C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylborylcarbonyl; di(C1-C30) alkylborylcarbonyl; (C1-C30) alkyl (C6-C30) arylborylcarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, the substituents are each independently selected from at least one of the group consisting of: (C1-C6) alkyl, (C6-C15) aryl and (5- to 15-membered) heteroaryl. Specifically, the substituents each independently may be at least one selected from the group consisting of a methyl group, a phenyl group, and a naphthyl group.

[0032] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0033] In Formula 1, X1 represents -N(L1)(R5)-, -O-, -S- or -C(R6)(R7)-; Y1 represents -N=, -N(R8)-, -O-, -S-, -C(R9)= or -C(R 10 )(R 11 )-; and Y2 represents -N- or -C=.

[0034] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C15) arylene, or a substituted or unsubstituted (5- to 15-membered) heteroarylene. According to another embodiment of the present disclosure, L1 and L2 each independently represent a single bond, or an unsubstituted (C6-C15) arylene. Specifically, L1 and L2 each independently may represent a single bond, a phenylene, a naphthylene, a biphenylene, etc.

[0035] Furthermore, L1 and L2 each independently represent a single bond, or any one of the following R-1 to R-4.

[0036]

[0037] R1 to R3 and R6 to R 11 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-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) alkyl(C6-C30) aryl The present invention may be a substituted or unsubstituted (C1-C30)alkylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be connected to an adjacent substituent to form a ring.

[0038] According to one embodiment of the present disclosure, R1 to R3 each independently represents hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (5- to 15-membered) heteroaryl; or may be connected with adjacent substituents to form a ring. According to another embodiment of the present disclosure, R1 to R3 each independently represents hydrogen, unsubstituted (C6-C15) aryl, or unsubstituted (5- to 15-membered) heteroaryl; or may be connected with adjacent substituents to form a ring. Specifically, R1 to R3 each independently represents hydrogen, phenyl, pyridyl, etc.; or may be connected with adjacent substituents to form a benzene ring.

[0039] According to one embodiment of the present disclosure, R6 to R 11 Each independently represents a substituted or unsubstituted (C1-C6) alkyl group, or a substituted or unsubstituted (C6-C15) aryl group. According to another embodiment of the present disclosure, R6 to R 11 Each independently represents an unsubstituted (C1-C6) alkyl group or an unsubstituted (C6-C15) aryl group. 11 Each independently represents a methyl group, a phenyl group, or the like.

[0040] R4 and R5 each independently represent a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C30) arylamino group. According to one embodiment of the present disclosure, R4 and R5 each independently represent a substituted or unsubstituted (C6-C15) aryl group, a substituted or unsubstituted (5- to 15-membered) heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C15) arylamino group. According to another embodiment of the present disclosure, R4 and R5 each independently represent an unsubstituted (C6-C15)aryl group; an unsubstituted or substituted (5- to 15-membered)heteroaryl group; an unsubstituted or substituted (5- to 15-membered)heteroaryl group; an unsubstituted or substituted (C6-C15)aryl group and a (5- to 15-membered)heteroaryl group; or an unsubstituted or substituted (C1-C6)alkyl mono- or di-(C6-C15)arylamino group. Specifically, R4 and R5 each independently represent phenyl; naphthyl; biphenyl; pyridyl; pyridyl substituted by phenyl; pyrimidinyl substituted by phenyl, naphthyl, dibenzofuranyl and / or dibenzothienyl; triazine substituted by phenyl, naphthyl, biphenyl, dibenzofuranyl and / or dibenzothienyl; quinazolinyl substituted by phenyl; quinoxalinyl substituted by phenyl and / or naphthyl; benzoquinazolinyl substituted by phenyl and / or naphthyl; benzoquinoxalinyl substituted by phenyl, naphthyl and / or pyridyl; carbazolyl; diphenylamino; phenyldimethylfluorenylamino, etc.

[0041] a represents an integer of 1 or 2; b represents an integer of 1 to 3; c represents an integer of 1 to 4; wherein if a to c are each independently an integer of 2 or greater, each of R1, each of R2, and each of R3 may be the same or different. According to one embodiment of the present disclosure, a, b, and c each independently represent an integer of 1 or 2.

[0042] According to one embodiment of the present disclosure, in Formula 1, X1 represents -N(L1)(R5)-, -O-, -S- or -C(R6)(R7)-; Y1 represents -N=, -N(R8)-, -O-, -S-, -C(R9)= or -C(R 10 )(R 11 )-; Y2 represents -N- or -C=; L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C15)arylene group, or a substituted or unsubstituted (5- to 15-membered)heteroarylene group; R1 to R3 each independently represent hydrogen, a substituted or unsubstituted (C6-C15)aryl group, or a substituted or unsubstituted (5- to 15-membered)heteroaryl group; or may be linked to an adjacent substituent to form a ring; R4 and R5 each independently represent a substituted or unsubstituted (C6-C15)aryl group, a substituted or unsubstituted (5- to 15-membered)heteroaryl group, or a substituted or unsubstituted mono- or di-(C6-C15)arylamino group; R6 to R 11 Each independently represents a substituted or unsubstituted (C1-C6) alkyl group, or a substituted or unsubstituted (C6-C15) aryl group; and a, b and c each independently represent 1 or 2.

[0043] According to another embodiment of the present disclosure, in Formula 1, X1 represents -N(L1)(R5)-, -O-, -S- or -C(R6)(R7)-; Y1 represents -N=, -N(R8)-, -O-, -S-, -C(R9)= or -C(R 10 )(R 11 )-; Y2 represents -N- or -C=; L1 and L2 each independently represent a single bond, or an unsubstituted (C6-C15)arylene group; R1 to R3 each independently represent hydrogen, an unsubstituted (C6-C15)aryl group, or an unsubstituted (5- to 15-membered)heteroaryl group; or may be linked to adjacent substituents to form a ring; R4 and R5 each independently represent an unsubstituted (C6-C15)aryl group; an unsubstituted or (C6-C15)aryl (5- to 15-membered)heteroaryl group; or an unsubstituted or (C1-C6)alkyl-substituted mono- or di-(C6-C15)arylamino group; R6 to R 11 Each independently represents an unsubstituted (C1-C6) alkyl group or an unsubstituted (C6-C15) aryl group; and a, b and c each independently represent 1 or 2.

[0044] In the formula of the present disclosure, if adjacent substituents are connected to each other to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3 to 30 yuan) alicyclic ring or aromatic ring, or a combination thereof, wherein the formed ring may contain at least one heteroatom selected from nitrogen, oxygen and sulfur. For example, the condensed ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0045] Herein, the (sub)heteroaryl group may contain at least one heteroatom selected from B, N, O, S, Si and P. In addition, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, tritium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- 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) alkylsilyl, substituted or unsubstituted di(C6 ... 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)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0046] The compound represented by Formula 1 includes the following compounds, but is not limited thereto.

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] The compounds having Formula 1 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art and, for example, as shown in the following reaction scheme, but are not limited thereto.

[0056] [Reaction Scheme 1]

[0057]

[0058] [Reaction Scheme 2]

[0059]

[0060] [Reaction Scheme 3]

[0061]

[0062]

[0063] [Reaction Scheme 4]

[0064]

[0065] [Reaction Scheme 5]

[0066]

[0067] [Reaction Scheme 6]

[0068]

[0069] In Reaction Schemes 1 to 6, Y1, L2, R1 to R4, R6, R7, R9 and a to c are as defined in Formula 1.

[0070] Although illustrative synthesis examples of the compounds represented by Formula 1 are described above, those skilled in the art will be able to easily understand that they are all based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont)-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd (II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, and the above reactions proceed even if substituents defined in the above Formula 1 but not specified in the specific synthesis example are bonded.

[0071] The present disclosure provides an organic electroluminescent material including a compound represented by Formula 1, and an organic electroluminescent device including the organic electroluminescent material.

[0072] The organic electroluminescent material may consist of only the compound according to the present disclosure, or may further contain conventional materials included in organic electroluminescent materials.

[0073] The organic electroluminescent compound represented by Formula 1 of the present disclosure may be included in at least one of a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, preferably, it may be included in a light-emitting layer. When used in a light-emitting layer, the organic electroluminescent compound represented by Formula 1 of the present disclosure may be included as a host material. Preferably, the light-emitting layer may further include at least one dopant. If necessary, the organic electroluminescent compound of the present disclosure may be used as a co-host material. That is, the light-emitting layer may further include an organic electroluminescent compound other than the organic electroluminescent compound represented by Formula 1 of the present disclosure (first host material) as a second host material. The weight ratio between the first host material and the second host material is 1:99 to 99:1. When two or more materials are included in a layer, mixed deposition may be performed to form a layer, or co-deposition may be performed separately to form a layer.

[0074] The second host material may be selected from any known host material. Preferably, the second host material may be selected from the group consisting of compounds represented by the following formulae 11 to 16:

[0075] H-(Cz-L4) h -M (11)

[0076] H-(Cz) i -L4-M (12)

[0077]

[0078]

[0079] Wherein, Cz represents the following structure:

[0080]

[0081] A represents -O- or -S-; R 21 To R 24 Each independently represents hydrogen, tritium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, or -SiR 25 R 26 R 27 ; R 25 To R 27Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; L4 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group; M represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; Y1 and Y2 each independently represent -O-, -S-, -N(R 31 )-or-C(R 32 )(R 33 )-, and Y1 and Y2 do not exist at the same time; R 31 To R 33 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group, R 32 and R 33 may be the same or different; h and i each independently represent an integer from 1 to 3; j, k, l and m each independently represent an integer from 0 to 4; q represents an integer from 1 to 3; and wherein h, i, j, k, l, m or q is an integer of 2 or more, each of (Cz-L4), each of (Cz), R 21 Each of R 22 Each of R 23 Each of the R 24 Each of can be the same or different.

[0082]

[0083] In Formula 16, Y3 to Y5 each independently represent CR 34 or N; R 34 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5- to 30-membered)heteroaryl; B1 and B2 each independently represent hydrogen, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5- to 30-membered)heteroaryl; B3 represents substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5- to 30-membered)heteroaryl; and L5 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (5- to 30-membered)heteroarylene.

[0084] Specifically, examples of the second host material include the following, but are not limited thereto.

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Here, TPS represents triphenylsilyl.

[0092] The dopant contained in the organic electroluminescent device of the present disclosure is at least one phosphorescent dopant or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complex compounds, more preferably selected from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complex compounds, and even more preferably ortho-metallized iridium complex compounds.

[0093] The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following Formula 101, but is not limited thereto.

[0094]

[0095] In Formula 101, L is selected from the following structures 1 and 2:

[0096]

[0097] R 100 To R 103 Each independently represents hydrogen, tritium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be combined with adjacent R 100 To R 103 linked to form a substituted or unsubstituted fused ring with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

[0098] R 104 To R 107Each independently represents hydrogen, tritium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be combined with adjacent R 104 To R 107 connected to form a substituted or unsubstituted fused ring with benzene, such as substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine;

[0099] R 201 To R 211 Each independently represents hydrogen, tritium, halogen, unsubstituted or tritium- or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be combined with adjacent R 201 To R 211 connected to form a substituted or unsubstituted fused ring; and

[0100] n represents an integer of 1 to 3.

[0101] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0102]

[0103]

[0104]

[0105]

[0106] An organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

[0107] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include a light-emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each layer may further consist of multiple layers.

[0108] The first electrode and the second electrode may each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a two-side emission type. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0109] The organic layer may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.

[0110] In addition, in the organic electroluminescent device of the present disclosure, the organic layer may further contain at least one metal selected from the group consisting of: metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, organic metals of lanthanide elements and d-transition elements, or at least one complex compound containing the metal.

[0111] The organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer containing a blue, red or green light-emitting compound known in the art. In addition, if necessary, it can further comprise a yellow or orange light-emitting layer.

[0112] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter, "surface layer") may be preferably placed on one or more inner surfaces of one or both electrodes. Specifically, a chalcogenide (including oxide) layer of silicon or aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The surface layer can provide operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0113] A hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer or an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be a multilayer so as to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be a multilayer.

[0114] An electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be a multilayer to control the injection of electrons and improve the interface characteristics between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds at the same time. The hole blocking layer or the electron transport layer may also be a multilayer, wherein each of the multilayers may use a plurality of compounds.

[0115] The luminescence auxiliary layer can be placed between the anode and the luminescent layer, or between the cathode and the luminescent layer. When the 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. When the 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, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer, and the hole transport rate (or hole injection rate) can be effectively promoted or blocked, so that the charge balance can be controlled. In addition, the electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the luminescent layer, and the overflow electrons from the luminescent layer can be blocked and the excitons can be confined in the luminescent layer to prevent light leakage. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included can be used as a hole auxiliary layer or an electron blocking layer. The luminescence auxiliary layer, the hole auxiliary layer or the electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0116] In the organic electroluminescent device of the present disclosure, it is preferred to place a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers that emit white light.

[0117] According to one embodiment of the present disclosure, an organic electroluminescent material may be used as a light-emitting material for a white organic light-emitting device. According to the arrangement of R (red), G (green), B (blue) or YG (yellow-green) light-emitting units, a white organic light-emitting device having various structures has been proposed, such as a parallel arrangement (side by side) method, a stacking method, or a color conversion material (CCM) method, etc. In addition, according to one embodiment of the present disclosure, the organic electroluminescent material may also be applied to an organic electroluminescent device including QD (quantum dots).

[0118] To form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating, etc., or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating, etc. can be used. The first and second host compounds of the present disclosure can be co-evaporated or mixed evaporated.

[0119] When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing a material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. There is no particular limitation on the solvent as long as the material constituting each layer is soluble or dispersible in the solvent, which does not cause any problem in forming a film.

[0120] A display system, such as a display system for a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a car; or a lighting system, such as an outdoor or indoor lighting system, can be produced by using the organic electroluminescent device of the present disclosure.

[0121] Hereinafter, the preparation method of the compounds of the present disclosure, and the characteristics of the compounds will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0122] Example 1: Preparation of Compound C-2

[0123]

[0124] Synthesis of compound 1-1

[0125] In a flask, 100 g of 1-fluoro-2-nitrobenzene (709 mmol), 121.9 g of 2-bromoaniline (709 mmol), 59.7 g of potassium hydroxide (1063 mmol) and 800 mL of dimethylformamide (DMF) were added, and the mixture was stirred at 150° C. for 4 hours. After the reaction was completed, the organic layer was extracted with dichloromethane, and the remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 83.8 g of compound 1-1 (yield: 40%).

[0126] Synthesis of Compound 1-2

[0127] In a flask, 83.8g of compound 1-1 (286mmol) and 322.5g of tin (II) chloride dihydrate (1429mmol) were dissolved in 1400mL of ethanol, and the mixture was refluxed for 1 hour. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 62.1g of compound 1-2 (yield: 83%).

[0128] Synthesis of Compounds 1-3

[0129] In a flask, 62.1 g of compound 1-2 (236 mmol), 25.1 g of benzaldehyde (236 mmol) and 472 mL of nitrobenzene were added, and the mixture was refluxed for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure. The remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 48.4 g of compound 1-3 (yield: 59%).

[0130] Synthesis of Compounds 1-4

[0131] In a flask, 48.4g of compound 1-3 (139mmol) and 460mL of tetrahydrofuran were added, and n-butyl lithium was slowly added dropwise at -78°C and stirred. After 1 hour, 39.1g of triisopropyl borate (208mmol) was slowly added dropwise and stirred at room temperature. After the reaction was completed, the reaction mixture was washed with an aqueous solution of ammonium chloride, and the organic layer was extracted with ethyl acetate. Remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 43.5g of compound 1-4 (yield: 88%).

[0132] Synthesis of Compounds 1-5

[0133] In a flask, 38.4g of compound 1-4 (122mmol), 31.8g of 1-bromo-2-chloro-3-nitrobenzene (134mmol), 7.1g of tetrakis (triphenylphosphine) palladium (0) (6mmol) and 99.6g of cesium carbonate (306mmol) were dissolved in 600mL of toluene, 150mL of ethanol and 150mL of water, and the mixture was refluxed for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10.6g of compound 1-5 (yield: 20%).

[0134] Synthesis of Compounds 1-6

[0135] In a flask, 10 g of compound 1-5 (23 mmol), 1.05 g of palladium (II) acetate (5 mmol), 3.5 g of tricyclohexylphosphine tetrafluoroborate (9 mmol) and 23 g of cesium carbonate (70 mmol) were dissolved in 120 mL of o-xylene, and the mixture was stirred at 130° C. for 4 hours. After the reaction was completed, the solvent was removed, and the resulting mixture was separated by column chromatography to obtain 6.6 g of compound 1-6 (yield: 72%).

[0136] Synthesis of Compounds 1-7

[0137] In a flask, 6.3g of compound 1-6 (16mmol), 12.7g of triphenylphosphine (49mmol) and 80mL of 1,2-dichlorobenzene were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure. Remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 6g of compound 1-7 (yield: 105%).

[0138] Synthesis of compound C-2

[0139] In a flask, 3g of compound 1-7 (8mmol), 3.3g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8mmol), 0.3g of tris(dibenzylideneacetone)dipalladium (0) (0.34mmol), 0.3g of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (s-phos) (0.84mmol) and 2.0g of sodium tert-butoxide (21mmol) were dissolved in 55mL of o-xylene, and the mixture was refluxed. After the reaction was complete, the solvent was removed, and the resulting mixture was separated by column chromatography to obtain 3.4g of compound C-2 (yield: 61%).

[0140] Compound MW Melting point C-2 664.77 260℃

[0141] Example 2: Preparation of Compound C-6

[0142]

[0143] In a flask, 3g of compound 1-7 (8mmol), 2.22g of 2-chloro-3-phenylquinoxaline (9mmol), 5.5g of cesium carbonate (17mmol), 0.5g of 4-dimethylaminopyridine (DMAP) (4mmol) and 42mL of dimethyl sulfoxide (DMSO) were added, and the mixture was stirred at 100°C for 4 hours. After the reaction was completed, the reaction mixture was washed with an aqueous solution of ammonium chloride, and the organic layer was extracted with ethyl acetate. Remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3.4g of compound C-6 (yield: 72%).

[0144] Compound MW Melting point C-6 561.65 277℃

[0145] Example 3: Preparation of Compound C-49

[0146]

[0147] Synthesis of compound 1

[0148] In a flask, 50g of 2-chloroaniline (392mmol), 1250mL of acetonitrile and 625mL of water are added, and 130mL of hydrochloric acid is slowly dripped at 0°C, and the mixture is stirred for 30 minutes. The aqueous solution prepared by dissolving 40g of sodium nitrite (588mmol) in 500mL of water at -5°C is slowly dripped into the reaction mixture and stirred for 30 minutes. At 0°C, 82mL of pyrrolidine (979.85mmol) dissolved in 400mL of acetonitrile and 282g of potassium carbonate (2038mmol) dissolved in 200mL of water are dripped into the reaction mixture, and the mixture is stirred at room temperature for 1 hour. After the reaction is complete, the organic layer is extracted with ethyl acetate. Residual moisture is removed by using magnesium sulfate. The residue is dried and separated by column chromatography to obtain 38.7g of compound 1 (yield: 47%).

[0149] Synthesis of compound 2

[0150] In a flask, 28.5 g of compound 1 (136 mmol), 48.5 g of diphenylacetylene (272 mmol), 4.2 g of pentamethylcyclopentadienyl rhodium chloride (III) dimer (6.8 mmol), 9.35 g of silver (V) hexafluoroantimonate (27.2 mmol), 54.3 g of copper acetate (II) monohydrate (272 mmol) and 1360 mL of methanol were added, and the mixture was stirred at 90° C. for 24 hours. After the reaction was completed, the organic solvent was removed, and the reaction mixture was separated by column chromatography to obtain 27.6 g of compound 2 (yield: 67%).

[0151] Synthesis of compound 3

[0152] In a flask, add 27.6g of compound 2 (91mmol), 27.7g of bis (pinacol) diboron (109mmol), 4.2g of tris (dibenzylideneacetone) dipalladium (0) (4.5mmol), 3.7g of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (9mmol), 22.3g of potassium acetate (227mmol) and 450mL of 1,4-dioxane, and the mixture was refluxed for 6 hours. After the reaction was complete, the organic solvent was removed, and the reaction mixture was separated by column chromatography to obtain 24.3g of compound 3 (yield: 68%).

[0153] Synthesis of compound 4

[0154] In a flask, 9g of 2-bromo-1-chloro-3-nitrobenzene (41mmol), 24.3g of compound 3 (61mmol), 2.4g of tetrakis (triphenylphosphine) palladium (0) (2mmol) and 33.4g of cesium carbonate (102mmol) were dissolved in 205mL of toluene, 50mL of ethanol and 50mL of water, and the mixture was refluxed for 24 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. Residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 12g of compound 4 (yield: 69%).

[0155] Synthesis of compound 5

[0156] In a flask, add 12g of compound 4 (28mmol), 8.8g of 2-chlorophenylboric acid (57mmol), 1.3g of tris (dibenzylideneacetone) dipalladium (0) (1.4mmol), 1.2g of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (2.8mmol), 30g of tripotassium phosphate (141mmol) and 140mL of toluene, and reflux the mixture for 5 hours. After the reaction is complete, the organic layer is extracted with ethyl acetate. Residual moisture is removed by using magnesium sulfate. Residue is dried and separated by column chromatography to obtain 4.6g of compound 5 (yield: 33%).

[0157] Synthesis of compound 6

[0158] In a flask, 4.3 g of compound 5 (8.6 mmol), 0.55 g of copper powder (8.6 mmol), 4.8 g of potassium carbonate (34 mmol) and 43 mL of nitrobenzene were added, and the mixture was stirred at 230 ° C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure. The remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3 g of compound 6 (yield: 75%).

[0159] Synthesis of compound 7

[0160] In a flask, 3g of compound 6 (6.5mmol), 5.1g of triphenylphosphine (19mmol) and 43mL of 1,2-dichlorobenzene were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure. Remaining moisture was removed by using magnesium sulfate. Residue was dried and separated by column chromatography to obtain 2.8g of compound 7 (yield: 100%).

[0161] Synthesis of compound C-49

[0162] In a flask, 2.8g of compound 7 (6.5mmol), 1.7g of 2-chloro-3-phenylquinoxaline (7.1mmol), 4.2g of cesium carbonate (13mmol), 0.4g of 4-dimethylaminopyridine (3.2mmol) and 32mL of dimethyl sulfoxide (DMSO) were added, and the mixture was stirred for 5 hours at 100°C. After the reaction was completed, the reaction mixture was washed with an aqueous solution of ammonium chloride, and the organic layer was extracted with ethyl acetate. Remaining moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.3g of compound C-49 (yield: 56%).

[0163] Compound MW Melting point C-49 636.76 285℃

[0164] Device Examples 1 to 3: Production of OLEDs with Compound Silk Deposited as Hosts According to the Disclosure

[0165] The OLED according to the present disclosure was produced as follows: a transparent electrode indium tin oxide (ITO) thin film (10Ω / sq) on a glass substrate for OLED (GEOMATEC CO., LTD., Japan) was ultrasonically cleaned with acetone, ethanol and distilled water in sequence, and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6Tolerance. Thereafter, an electric current is applied to the chamber to evaporate the above introduced materials, thereby forming a first hole injection layer with a thickness of 80nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5nm on the first hole injection layer. Compound HT-1 is then introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10nm on the second hole injection layer. Compound HT-2 is then introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: the host material shown in Table 1 is introduced into a chamber of a vacuum vapor deposition device as a host, and compound D-39 is introduced into another chamber as a dopant. The two materials were evaporated at different rates and the dopant was deposited at a doping amount of 3wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Next, compound ET-1 and compound E1-1 were evaporated in a ratio of 1:1 in two other chambers to deposit an electron transport layer with a thickness of 35nm on the light-emitting layer. After compound EI-1 was deposited as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED was produced.

[0166] Comparative Example 1: Production of OLEDs with Comparative Compounds Deposited as Hosts

[0167] An OLED was produced in the same manner as in Device Example 1, except that Compound A shown in Table 2 was used as a host of the light-emitting layer.

[0168] [Table 1]

[0169]

[0170] The OLED produced by using the organic electroluminescent compound according to the present disclosure as a host exhibits lower driving voltage, higher luminous efficiency, and longer lifespan characteristics compared to the OLED produced by using the comparative compound as a host.

[0171] [Table 2]

[0172]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 1: in X1 represents -N(L1-R5)-; Y1 represents -N= or -C(R9)=; Y2 represents -N-; L1 and L2 each independently represent a single bond, or a deuterium-substituted or unsubstituted C6-C30 arylene group; R1 to R3 each independently represent hydrogen, deuterium, halogen, cyano or substituted or unsubstituted C1-C30 alkyl; R4 and R9 each independently represent a deuterium-substituted or unsubstituted C6-C30 aryl group; R5 represents a substituted or unsubstituted 3- to 30-membered heteroaryl group; and a represents an integer of 1 or 2; b represents an integer of 1 to 3; c represents an integer of 1 to 4; wherein if a to c are each independently an integer of 2 or more, each of R1, each of R2 and each of R3 may be the same or different, in, In R1 to R3 and R5, the substituents of the substituted C1-C30 alkyl group and the substituted 3- to 30-membered heteroaryl group are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; C1-C30 alkyl group; halogenated C1-C30 alkyl group; C2-C30 alkenyl group; C2-C30 alkynyl group; C1-C30 alkoxy group; C1-C30 alkylthio group; C3-C30 cycloalkyl group; C3-C30 cycloalkenyl group; 3- to 7-membered heterocycloalkyl group; C6-C30 aryloxy group; C6-C30 arylthio group; 5- to 30-membered heteroaryl group which is unsubstituted or substituted by C6-C30 aryl group; C6-C30 aryl group which is unsubstituted or substituted by 5- to 30-membered heteroaryl group; tri-C1-C30 alkyl group Silyl; tri-C6-C30 arylsilyl; di-C1-C30 alkyl C6-C30 arylsilyl; C1-C30 alkyl di-C6-C30 arylsilyl; amino; mono- or di-C1-C30 alkylamino; mono- or di-C6-C30 arylamino unsubstituted or substituted by C1-C30 alkyl; C1-C30 alkyl C6-C30 arylamino; C1-C30 alkylcarbonyl; C1-C30 alkoxycarbonyl; C6-C30 arylcarbonyl; di-C6-C30 arylborylcarbonyl; di-C1-C30 alkylborylcarbonyl; C1-C30 alkyl C6-C30 arylborylcarbonyl; C6-C30 aryl C1-C30 alkyl; and C1-C30 alkyl C6-C30 aryl.

2. The organic electroluminescent compound according to claim 1, wherein L1 and L2 each independently represent a single bond, or any one of the following R-1 to R-4:

3. The organic electroluminescent compound according to claim 1, wherein L1 and L2 each independently represent a single bond, or an unsubstituted C6-C15 arylene group; R1 to R3 each independently represent hydrogen; R4 and R9 each independently represent an unsubstituted C6-C15 aryl group; R5 represents a substituted or unsubstituted 5- to 15-membered heteroaryl group; and a, b and c each independently represent 1 or 2, wherein, in R5, the substituents of the substituted 5- to 15-membered heteroaryl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; C1-C30 alkyl; halogenated C1-C30 alkyl; C2-C30 alkenyl; C2-C30 alkynyl; C1-C30 alkoxy; C1-C30 alkylthio; C3-C30 cycloalkyl; C3-C30 cycloalkenyl; 3- to 7-membered heterocycloalkyl; C6-C30 aryloxy; C6-C30 arylthio; 5- to 30-membered heteroaryl, unsubstituted or substituted by C6-C30 aryl; C6-C30 aryl, unsubstituted or substituted by 5- to 30-membered heteroaryl; tri-C1-C30 alkylsilyl; tri-C6 -C30 arylsilyl; di-C1-C30 alkyl C6-C30 arylsilyl; C1-C30 alkyl di-C6-C30 arylsilyl; amino; mono- or di-C1-C30 alkylamino; mono- or di-C6-C30 arylamino unsubstituted or substituted by C1-C30 alkyl; C1-C30 alkyl C6-C30 arylamino; C1-C30 alkylcarbonyl; C1-C30 alkoxycarbonyl; C6-C30 arylcarbonyl; di-C6-C30 arylborylcarbonyl; di-C1-C30 alkylborylcarbonyl; C1-C30 alkyl C6-C30 arylborylcarbonyl; C6-C30 arylC1-C30 alkyl; and C1-C30 alkyl C6-C30 aryl.

4. The organic electroluminescent compound according to claim 1, wherein L1 and L2 each independently represent a single bond, or an unsubstituted C6-C15 arylene group; R1 to R3 each independently represent hydrogen; R4 and R9 each independently represent an unsubstituted C6-C15 aryl group; R5 represents a 5- to 15-membered heteroaryl group which is unsubstituted or substituted with a C6-C15 aryl group; a 5- to 15-membered heteroaryl group which is substituted with a C6-C15 aryl group and a 5- to 15-membered heteroaryl group; and a, b and c each independently represent 1 or 2.

5. The organic electroluminescent compound according to claim 1, wherein The compound represented by Formula 1 is selected from the group consisting of the following compounds: An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1 . 7 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

8. The organic electroluminescent device according to claim 7, wherein: The organic electroluminescent compound is contained in the light emitting layer.

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