Organic electroluminescent compounds, organic electroluminescent materials containing the same, and organic electroluminescent devices

Abstract

To provide an organic electroluminescent material effective in producing an organic electroluminescent device having low driving voltage, high luminous efficiency and a long lifespan.SOLUTION: The invention provides an organic electroluminescent compound represented by formula (1), and an organic electroluminescent device comprising the compound as a host material.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material containing the compound, and an organic electroluminescent device.

Background Art

[0002] An electroluminescent device (EL device) is a self-emitting display device having advantages such as a wider viewing angle, a larger contrast ratio, and a faster response time. In 1987, the first organic EL device was developed by Eastman Kodak by using small aromatic diamine molecules and an aluminum complex as materials for forming a light-emitting layer (Non-Patent Document 1).

[0003] The most important factor in determining the luminous efficiency in an organic electroluminescent device (OLED) is the light-emitting material. So far, fluorescent materials have been widely used as light-emitting materials. However, in terms of the electroluminescent mechanism, phosphorescent light-emitting materials have been widely studied because they theoretically increase the luminous efficiency by four times compared to fluorescent light-emitting materials. So far, iridium(III) complexes have been widely known as phosphorescent light-emitting materials such as bis(2-(2'-benzothienyl)-pyridinato-N,C-3')iridium(acetylacetonate) [(acac)Ir(btp)2], tris(2-phenylpyridine)iridium [Ir(ppy)3], and bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium (Firpic) as red, green, and blue light-emitting materials, respectively.

[0004] In prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, Pioneer et al. (Japan) developed high-performance OLEDs using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)(BAlq) as host materials, which were known as hole-blocking materials.

[0005] However, while conventional materials offer excellent luminescence properties, they have the following drawbacks: (1) Due to their low glass transition temperature and insufficient thermal stability, degradation can occur during high-temperature deposition processes in vacuum, potentially reducing the device's lifespan. (2) The power efficiency of an OLED is given by [(π / voltage) × current efficiency], and power efficiency is inversely proportional to voltage. OLEDs containing phosphorescent host materials yield higher current efficiency (cd / A) than those containing fluorescent materials, but require significantly higher driving voltages. Therefore, they offer no advantage in terms of power efficiency (lm / W). (3) Furthermore, OLEDs have a short operating life, and further improvements in luminescence efficiency are needed.

[0006] Various materials and concepts have been proposed for the organic layer of OLEDs to improve luminous efficiency, operating voltage, and / or lifespan, but these have not been satisfactory for practical applications. [Prior art documents] [Non-patent literature]

[0007] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 [Overview of the project] [Problems that the invention aims to solve]

[0008] The object of this disclosure is, firstly, to provide organic electroluminescent compounds and organic electroluminescent materials containing the same that are effective for manufacturing organic electroluminescent devices having a low drive voltage and / or high luminescence efficiency and / or long life; and secondly, to provide organic electroluminescent devices containing the organic electroluminescent material. [Means for solving the problem]

[0009] As a result of intensive research to solve the above technical problems, the inventors have found that the aforementioned objectives can be achieved by an organic electroluminescent compound represented by the following formula 1, and have completed the present invention. [ka]

[0010] In Equation 1, Rings A and B each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; X1 to X3 each independently represent either N or CR11; R2 and R11 may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3-N-(Ar2)(Ar3), or may be linked with adjacent substituents to form a ring; L3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar2 and Ar3 independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; L1, L2, and R3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene, provided that R2 is linked to the adjacent R11 to form a fused ring, then L2 represents a single bond; Y1 represents a single bond, -O-, -S-, -N-Ar1, -R12C=CR12'-, -R13R14C-CR13'R14'-, or -CR15R16, provided that L1 is linked to Y1, then Y1 represents -N-; Ar1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R12-R16, R12', R13', and R14' may each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be linked with adjacent substituents to form a ring; m and n each represent an integer of either 1 or 2 independently; If m and n are 2 or greater, L1 and L2 may be the same or different.

[0011] Advantageous effects of the invention By including the organic electroluminescent compounds and organic electroluminescent materials containing the same according to this disclosure, it is possible to manufacture organic electroluminescents having a low drive voltage and / or high luminescence efficiency and / or long lifetime. [Modes for carrying out the invention]

[0012] This specification further describes the present disclosure. However, the following description is intended to illustrate the present invention and is not intended to limit the scope of the invention in any way.

[0013] This disclosure relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material containing the organic electroluminescent compound, and an organic electroluminescent device containing the organic electroluminescent material.

[0014] In this disclosure, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any material layer constituting the organic electroluminescent device.

[0015] In this specification, “organic electroluminescent material” means a material that can be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emission material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0016] In this specification, “multiple host materials” means an organic electroluminescent material comprising a combination of at least two host materials. This may mean both materials before (e.g., before deposition) and materials after (e.g., after deposition) the organic electroluminescent device is included. The multiple host materials of this disclosure may be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds included in the multiple host materials of this disclosure may be included in one light-emitting layer or each may be included in different light-emitting layers. If at least two host materials are included in one layer, the at least two host materials may be mixed and evaporated to form the layer, or they may be co-evaporated simultaneously and individually to form the layer.

[0017] In this specification, "(C1-C30) alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The alkyls may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. In this specification, the term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The cycloalkyls may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. In this specification, "(C6-C30) aryl(ene)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton (the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15), which may be partially saturated and may contain a spiro structure. Examples of aryl compounds include, specifically, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenantrenyl, benzophenantrenyl, phenylphenantrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, coumenyl, spiro[fluoren-fluorenyl]yl, spiro[fluoren-benzofluorenyl]yl, azlenyl, and others. More specifically, aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, 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, Possible candidates include 9-diphenyl-4-fluorenyl, 1-antryl, 2-antryl, 9-antryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, etc. In this specification, "(3-30 member) heteroaryl(ene)" is an aryl having 3 to 30 ring skeleton atoms (preferably 5 to 25 ring skeleton atoms) and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge. The heteroaryl may be a monocyclic ring or a fused ring fused with at least one benzene ring; it may also be partially saturated. Furthermore, the heteroaryl in this specification may be formed by bonding at least one heteroaryl group or aryl group to a heteroaryl group by a single bond. Examples of heteroaryls include, specifically, monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridadinyl; and,Examples of condensed ring heteroaryls include benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenantridinyl, benzodioxolyl, indolididinyl, acrylidinyl, silafluorenyl, and germafluorenyl. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, and 1-pyrazo Lil, 1-Indolizidinyl, 2-Indolizidinyl, 3-Indolizidinyl, 5-Indolizidinyl, 6-Indolizidinyl, 7-Indolizidinyl, 8-Indolizidinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl Drill, 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-benzofuranil, 3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 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, 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-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2- Methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-t-butyl-1-indolly, 4-t-butyl-1-indolly These may include 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl, etc. In this specification, "halogen" includes F, Cl, Br, and I.

[0018] Furthermore, "ortho (o)", "meta (m)", and "para (p)" all mean to indicate the substitution positions of all substituents. 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 directly adjacent substitution positions, for example, a compound having substituents at the 1- and 3-positions of benzene. The para position is the substitution position next to the meta position, for example, a compound having substituents at the 1- and 4-positions of benzene.

[0019] As used herein, the term "ring formed by linking adjacent substituents" means a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof formed by linking or condensing two or more adjacent substituents, and preferably may be a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Further, 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. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20, and according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the linked or condensed ring may be, for example, 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, etc. [[ID=​​In addition, the term "substituted" in the expression "substituted or unsubstituted" in this disclosure means that a hydrogen atom in a particular functional group is replaced by another atom or functional group, i.e., a substituent. The substituents of substituted (C1-C30) alkyl, substituted (C2-C30) alkenyl, substituted (C6-C30) aryl(ene), substituted (3-30 member) heteroaryl(ene), 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, and substituted condensed rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings are each independently of deuterium, halo Gen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or (C6-C30) substituted (5-30 member) hetero Aryl, unsubstituted or (5-30 member) heteroaryl (C6-C30) aryl, tri(C1-C30) alkylsilyl, tri(C6-C30) arylsilyl, di(C1-C30) alkyl(C6-C30) arylsilyl, (C1-C30) alkyldi(C6-C30) arylsilyl, condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, amino, mono- or di-(C1-C30) alkylamino, mono- or di-(C2-C30) alkenylamino, (C1~C30) alkyl(C2~C30) alkenylamino, mono- or di-(C6~C30) arylamino, (C1~C30) alkyl(C6~C30) arylamino, mono- or di-(3~30 member) heteroarylamino, (C1~C30) alkyl(3~30 member) heteroarylamino, (C2~C30) alkenyl(C6~C30) arylamino, (C2~C30) alkenyl(3~30 member) heteroarylamino, (C6~C30) aryl(3~30 member) heteroarylamino,(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, and is at least one selected from the group consisting of. For example, the substituent may be methyl, cyano, triphenylsilyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, carbazolyl, dibenzothiophenyl, spirobifluorenyl, benzofluorocarbazolyl, benzothienocarbazolyl, triphenylenyl, or fluorenyl which is unsubstituted or substituted with at least one phenyl and methyl, etc.

[0021] Hereinafter, an organic electroluminescent compound according to an embodiment will be described.

[0022] An organic electroluminescent compound according to an embodiment is represented by the following formula 1.

Chemical formula

[0023] In formula 1, Ring A and ring B each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; X1 to X3 each independently represent N or CR11; R2 and R11 may independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3-N-(Ar2)(Ar3), or may be linked with adjacent substituents to form a ring; L3 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar2 and Ar3 independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; L1, L2, and R3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene, provided that R2 is linked to the adjacent R11 to form a fused ring, then L2 represents a single bond; Y1 represents a single bond, -O-, -S-, -N-Ar1, -R12C=CR12'-, -R13R14C-CR13'R14'-, or -CR15R16, provided that L1 is connected to Y1, then Y1 represents -N-; Ar1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R12-R16, R12', R13', and R14' may each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be linked with adjacent substituents to form a ring; m and n each represent an integer of either 1 or 2 independently; If m and n are 2 or greater, L1 and L2 may be the same or different.

[0024] In one embodiment, rings A and B may each independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 member) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-18 member) heteroaryl. For example, rings A and B may each independently be a benzene ring, a naphthalene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a spirobifluorene ring.

[0025] According to one embodiment, in formula (1) [ka] This can be expressed by any one of the following equations 1-1 to 1-13. [ka]

[0026] In equations 1-1 to 1-13, Y2 represents -O-, -S-, -N-Ar1, or -CR15R16; Y1, Ar1, R15, and R16 are as defined in Equation 1; R4~R6 and R4'~R6' are each independently defined as R2 in Equation 1; a, b, and c' each independently represent integers from 1 to 3, c to f each independently represent integers from 1 to 4, a' represents an integer from 1 to 5, and b' represents 1 or 2; If a~f and a'~c' are 2 or more, then R4'~R6' and R4~R6 may be the same or different.

[0027] According to another embodiment, in formula (1) [ka] This can be expressed by any one of the following equations 1-14 to 1-30. [ka] [ka]

[0028] In equations 1-14 to 1-30, Y2 represents -O-, -S-, -N-Ar1, or -CR15R16; R4~R6, R4'~R6', Y1, Ar1, R15, R16, a~f, and a'~c' are defined as shown in equations 1-1 to 1-13.

[0029] In one embodiment, X1 to X3 each independently represent N or CR11, preferably at least one of X1 to X3 is N, more preferably at least two of X1 to X3 are N, and even more preferably all of X1 to X3 are N, or all of them are CR11.

[0030] In one embodiment, R2 and R11 are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or Alternatively, unsubstituted tri(C6~C30)arylsilyl, substituted or unsubstituted condensed rings of an (C3~C30) aliphatic ring and a (C6~C30) aromatic ring, substituted or unsubstituted mono- or di-(C1~C30)alkylamino, substituted or unsubstituted mono- or di-(C2~C30)alkenylamino, substituted or unsubstituted (C1~C30)alkyl(C2~C30)alkenylamino, substituted or unsubstituted (C1~C30)alkyl(C6~C30)arylamino, substituted or unsubstituted Substituting (C1-C30) alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 member) heteroarylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 member) heteroaryl R2 represents an amino, or adjacent R2 and R11 may be linked to each other to form a substituted or unsubstituted (5-30 member) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, more preferably hydrogen, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-18 member) heteroaryl, or adjacent R2 and R11 may be linked to each other to form a (5-25 member) polycyclic aliphatic ring, aromatic ring, or a combination thereof. When R2 is linked to adjacent R11 to form a fused ring, L2 represents a single bond.For example, R2 and R11 may each independently be hydrogen, an unsubstituted or phenyl substituted with at least one of (C6-C30) aryl and (5-30 member) heteroaryl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted crisenyl, a substituted or unsubstituted pyrimidyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl, or they may be linked together to form a substituted or unsubstituted (5-30 member) monocyclic or polycyclic aromatic ring. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of N, O, and S, and more preferably at least one nitrogen (N). For example, R2 may be linked to the adjacent R11 to form a substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted naphthylidinyl, substituted or unsubstituted phenanthroquinoxalinyl, substituted or unsubstituted benzothienoquinazolinyl, substituted or unsubstituted benzofloxacolinyl, or substituted or unsubstituted dimethylindenoquinazolinyl.

[0031] According to one embodiment, the organic electroluminescent compound of formula 1 can be represented by the following formulas 2-1 or 2-2. [ka]

[0032] In equations 2-1 to 2-2, Rings A, B, Y1, R3, X1~X3, L1, L2, m, and n are defined as in Equation 1; X4 to X7 are each defined independently as X1 to X3 in Equation 1.

[0033] In one embodiment, L1, L2, and R3 each independently represent a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene, preferably a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 member) heteroarylene, more preferably a single bond, substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 member) heteroarylene. For example, L1, L2, and R3 may each be independently a single bond, unsubstituted or substituted with at least one of phenyl, biphenyl, triphenylenyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, and dibenzothiophenyl, phenylene, substituted or unsubstituted triphenylenyl, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted spirobifluorenylene, or substituted or unsubstituted dibenzofuranylene.

[0034] In one embodiment, Y1 represents a single bond, -O-, -S-, -N-Ar1, -R12C=CR12'-, -R13R14C-CR13'R14'-, or -CR15R16, but when L1 is linked to Y1, Y1 represents -N-, and Ar1 represents a substituted or unsubstituted (C6~C30) aryl or a substituted or unsubstituted (3~30 member) heteroaryl, preferably a substituted or unsubstituted (C6~C25) aryl or a substituted or unsubstituted (5~25 member) heteroaryl, more preferably a substituted or unsubstituted (C6~C18) aryl or a substituted or unsubstituted (5~18 member) heteroaryl; R12~R16, R12', R13', and R14' each independently represent hydrogen, substituted or unsubstituted (C1~C30) The substituents may be alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 member) heteroaryl, or may be linked to adjacent substituents to form a ring, preferably hydrogen, substituted or unsubstituted (C1-C20) alkyl, or substituted or unsubstituted aryl; they may be linked to adjacent substituents to form a substituted or unsubstituted (5-30 member) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, more preferably hydrogen, substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-C18) aryl, or may be linked to adjacent substituents to form a substituted or unsubstituted (5-25 member) monocyclic or polycyclic aromatic ring.

[0035] For example, Ar1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted carbazolyl.

[0036] R12-R16, R12', R13', and R14' may each independently represent hydrogen, a substituted or unsubstituted methyl atom, or a substituted or unsubstituted phenyl atom, or they may be linked to adjacent substituents, such as adjacent R13, R14, R13', and R14', or adjacent R15 and R16, to form a substituted or unsubstituted (5-25 member) polycyclic aromatic ring. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of N, O, and S.

[0037] According to one embodiment, the organic electroluminescent compound represented by Formula 1 above can be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0038] The organic electroluminescent compounds represented by Formula 1 according to this disclosure can be prepared as shown in the following reaction scheme 1 or 2; however, they may be further prepared by synthetic methods known to those skilled in the art. [ka]

[0039] In reaction schemes 1 and 2, the definition of substituents is as defined in Equation 1 above.

[0040] As described above, exemplary synthetic examples of compounds represented by Formula 1 according to one embodiment have been presented, which are based on reactions such as the Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction. Those skilled in the art will understand that the above reactions proceed even if other substituents defined in Formula 1 other than those described in the specific synthetic examples are attached.

[0041] According to one embodiment, the present disclosure provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.

[0042] According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may be formed solely of the organic electroluminescent compound of Formula 1, or it may further include other conventional materials included in the organic electroluminescent material. Specifically, the organic electroluminescent material of the present disclosure may include one or more compounds represented by Formula 1 above. For example, the compound of Formula 1 may be included in the light-emitting layer, and if the compound of Formula 1 is included in the light-emitting layer, the compound of Formula 1 may be included as a host, more specifically as a phosphorescent green host.

[0043] According to another embodiment of the present disclosure, the organic electroluminescent material of the present disclosure may further include an organic electroluminescent compound different from the organic electroluminescent compound of Formula 1 (first host material) as a second host material. That is, the organic electroluminescent material according to one embodiment of the present disclosure may include a plurality of host materials. Specifically, the plurality of host materials according to one embodiment may include at least one compound of Formula 1 as the first host material, and may also include at least one second host material different from the first host material. In this specification, the weight ratio of the first host material to the second host material may be in the range of 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30.

[0044] A second host material according to one embodiment comprises a compound represented by the following formula 11. [ka]

[0045] In Equation 11, La represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ara represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. R9 and R10 are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alke This represents a ylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) arylamino, or may be bonded to an adjacent substituent to form a ring; f and g each independently represent integers from 1 to 4; If f and g are 2 or greater, then each R9 and each R10 may be the same or different.

[0046] A second host material represented by formula 11 according to one embodiment can be represented by the following formulas 12 or 13. [ka]

[0047] In equations 12 and 13, La, Ara, R9, R10, and f are as defined in Equation 11; T1 and T2 each independently represent a single bond, O, or S; Lb is defined as La in Equation 11; Arb is defined as Ara in Equation 11; R11 to R14 are each defined independently as R9 in Equation 11; X1 represents O, S, or NRa; Ra represents a substituted or unsubstituted (C6-C30) aryl; g' and h each independently represent integers from 1 to 3, i and k each independently represent integers from 1 to 4, and j represents an integer of 1 or 2; If g', h, i, j, and k are 2 or greater, then each R10, each R11, each R12, each R13, and each R14 may be the same or different.

[0048] In one embodiment, La and Lb may each be independently single-bonded, substituted, or unsubstituted (C6-C30) arylene, preferably single-bonded, substituted, or unsubstituted (C6-C25) arylene, and more preferably single-bonded, substituted, or unsubstituted (C6-C18) arylene. For example, La and Lb may each be independently single-bonded, phenylene, or biphenylene.

[0049] In one embodiment, Ara and Arb each independently represent a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, more preferably an unsubstituted (C6-C30) aryl or a (5-30 member) heteroaryl (C6-C25) aryl. For example, Ara and Arb each independently represent an unsubstituted or substituted phenyl with at least one of methyl, cyano, triphenylsilane, phenyl, biphenyl, or naphthyl; an unsubstituted or phenyl-substituted carbazolyl; a substituted or unsubstituted o-biphenyl; a substituted or unsubstituted m-biphenyl; a substituted or unsubstituted p-terphenyl; a substituted or unsubstituted m-terphenyl; a substituted or unsubstituted o-terphenyl; a substituted or unsubstituted fluorenyl; an unsubstituted or phenyl-substituted naphthyl; or a substituted or unsubstituted triphenylenyl.

[0050] In one embodiment, Ra represents a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, and more preferably an unsubstituted (C6-C25) aryl or a (C6-C25) aryl substituted with a (C6-C30) aryl or a (5-30 member) heteroaryl. For example, Ra may be an unsubstituted or phenyl substituted with at least one of phenyl, biphenyl, or naphthyl, an unsubstituted or phenyl-substituted carbazolyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, an unsubstituted or phenyl-substituted naphthyl, or a substituted or unsubstituted triphenylenyl.

[0051] In one embodiment, R9 to R14 may each independently be hydrogen, a substituted or unsubstituted (C1 to C30) alkyl, a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30-membered) heteroaryl, preferably hydrogen, a substituted or unsubstituted (C1 to C10) alkyl, a substituted or unsubstituted (C6 to C25) aryl, or a substituted or unsubstituted (5 to 25-membered) heteroaryl, more preferably hydrogen, a substituted or unsubstituted (C1 to C4) alkyl, a substituted or unsubstituted (C6 to C18) aryl, or a substituted or unsubstituted (5 to 18-membered) heteroaryl. For example, R9 to R14 may each independently be hydrogen, a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted carbazolyl.

[0052] According to one embodiment, the compound represented by formula 11 can be more specifically exemplified by the following compounds, but is not limited to them. [ka] [ka] [ka] [ka] [ka]

[0053] The compounds of formula 11 according to this disclosure can be prepared by synthetic methods known to those skilled in the art.

[0054] The following describes an organic electroluminescent device applied to an organic electroluminescent material comprising the aforementioned organic electroluminescent compound and / or multiple host materials.

[0055] An organic electroluminescent device according to one embodiment may include a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode. The organic layer may include a light-emitting layer, and the light-emitting layer may include a plurality of host materials, including an organic electroluminescent compound represented by formula 1, or at least one first host material represented by formula 1 and at least one second host material represented by formula 11.

[0056] According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one compound from compounds C-1 to C-202 as a first host material represented by formula 1, and at least one compound from compounds H-1 to H-84 as a second host material represented by formula 11. These multiple host materials may be contained in the same organic layer, such as an emissive layer, or in different emissive layers. In addition to the emissive layer, the organic layer may further include at least one layer selected from hole injection layers, hole transport layers, hole auxiliary layers, emissive layer, electron transport layers, electron injection layers, intermediate layers, hole blocking layers, electron blocking layers, and electron buffer layers.

[0057] The organic layer may further contain amine compounds and / or azine compounds in addition to the light-emitting material of this disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may contain amine compounds as hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, or electron blocking material, such as arylamine compounds and styrylarylamine compounds. Furthermore, the electron transport layer, electron injection layer, electron buffer layer, or hole blocking layer may contain azine compounds as electron transport material, electron injection material, electron buffer material, or hole blocking material.

[0058] Furthermore, the organic layer may further contain at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds, and may further contain at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic d transition elements, or at least one complex compound containing such a metal.

[0059] An organic electroluminescent material according to one embodiment can be used as a light-emitting material for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting devices, such as parallel side-by-side arrangement, stacked arrangement, or color conversion material (CCM) method, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. In addition, the organic electroluminescent material according to one embodiment can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0060] One of the first and second electrodes may be an anode, and the other may be a cathode. In this case, the first and second electrodes can be formed from a permeable conductive material, a semi-permeable conductive material, or a reflective conductive material, respectively. Depending on the type of material used to form the first and second electrodes, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0061] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each layer may use two compounds simultaneously. The hole injection layer may be doped as a p-type dopant. An electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, preventing electron overflow from the light-emitting layer and thus confining excitons within the light-emitting layer to prevent light leakage. The hole transport layer or electron blocking layer may consist of multiple layers, in which case each layer may use multiple compounds.

[0062] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each layer may use two compounds simultaneously. The hole blocking layer is a layer between the electron transport layer (or electron injection layer) and the light-emitting layer, which prevents holes from arriving at the cathode, thereby improving the probability of electron-hole recombination in the light-emitting layer. The hole blocking layer or electron transport layer may also be multilayered, where each layer may use multiple compounds. The electron injection layer may also be doped as an n-type dopant.

[0063] A luminescence auxiliary layer may be placed between the anode and the luminescence layer, or between the cathode and the luminescence layer. When the luminescence auxiliary layer is placed between the anode and the luminescence layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the luminescence layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, a hole auxiliary layer may be placed between a hole transport layer (or hole injection layer) and the luminescence layer, and may be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. If the organic electroluminescent device includes two or more hole transport layers, any additionally included hole transport layers can be used as hole auxiliary layers or electron blocking layers. Luminescence auxiliary layers, hole auxiliary layers, or electron blocking layers may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0064] In the organic electroluminescent device of this disclosure, preferably at least one layer (hereinafter referred to as the "surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on the inner surface of one or both electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferably, chalcogenides include SiOX (1 ≤ X ≤ 2), AlOX (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.

[0065] Furthermore, in the organic electroluminescent device of this disclosure, preferably, a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant may be located on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, thus facilitating the injection and transport of electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thus facilitating the injection and transport of holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. An organic electroluminescent device having two or more light-emitting layers and emitting white light can be fabricated by using the reducing dopant layer as a charge-generating layer.

[0066] An organic electroluminescent device according to one embodiment may further include one or more dopants in the light-emitting layer.

[0067] The dopants contained in the organic electroluminescent materials of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of this disclosure is not particularly limited, but is preferably a metallized complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an orthometallated complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an orthometallated iridium complex compound.

[0068] The dopants included may be, but are not limited to, compounds represented by the following formula 101: [ka]

[0069] In Equation 101, L has the following structure 1 or 2: [ka] Selected from, Each of R100 to R103 can independently represent hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or bond with an adjacent substituent to form a ring with pyridine, such as a substituted or unsubstituted quinoline, substituted or unsubstituted benzoflopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofloxoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline ring; R104 to R107 can each independently represent hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1 to C30) alkoxy, or, in combination with adjacent substituents, form a ring with benzene, such as a substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzophropyridine, or substituted or unsubstituted benzothienopyridine ring; R201 to R211 each independently represent hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1 to C30) alkyl, substituted or unsubstituted (C3 to C30) cycloalkyl, or substituted or unsubstituted (C6 to C30) aryl, or can bond with adjacent substituents to form a ring. s represents an integer between 1 and 3.

[0070] In particular, specific examples of dopant compounds include, but are not limited to, the following. [ka] [ka] [ka] [ka]

[0071] To form each layer of the organic electroluminescent device of this disclosure, dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, or wet deposition methods such as spin coating, dip coating, and flow coating can be used. When using wet deposition methods, thin films can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent can be used as long as the material forming each layer can be dissolved or diffused and there are no problems with film formation ability.

[0072] When forming layers using first and second host materials according to one embodiment, the above method can be used, and the layers can often be formed by co-evaporation or mixed evaporation. Co-evaporation is a mixed evaporation method in which two or more isomer materials are placed in separate crucible sources and an electric current is passed through both cells simultaneously to evaporate the materials and perform mixed evaporation; mixed evaporation is a mixed evaporation method in which two or more isomer materials are mixed in one crucible source before evaporation, and then an electric current is passed through one cell to evaporate the materials.

[0073] According to one embodiment, when the first host material and the second host material are present in the same or different layers of an organic electroluminescent device, each of the two host materials can be deposited individually. For example, the second host material may be deposited after the first host material has been deposited.

[0074] According to one embodiment, the disclosure can provide a display device comprising a plurality of host materials, including a first host material represented by formula 1 and a second host material represented by formula 11. Furthermore, the disclosure can provide display devices such as those for smartphones, tablets, notebooks, PCs, televisions, or vehicles, or lighting devices such as outdoor or indoor lighting, by using an organic electroluminescent device.

[0075] The following describes the methods for preparing the compounds according to this disclosure, with regard to the synthesis methods of representative compounds or intermediate compounds of this disclosure, in order to understand this disclosure in detail. [Examples]

[0076] [Example 1] Synthesis of Compound C-1 [ka]

[0077] 1) Preparation of Compounds 1-2 Compound 1-1 (30 g, 84 mmol), (3-chlorophenyl)boronic acid (14 g, 92.2 mmol), Pd(PPh3)4 (4.9 g, 4.2 mmol), K2CO3 (23.2 g, 168 mmol), 336 mL of toluene, 84 mL of ethanol (EtOH), and 84 mL of water (H2O) were placed in a 3 L round-bottom flask (RBF) and refluxed at 140 °C for 1 hour. After the reaction was complete, the reaction mixture was cooled to room temperature, and the organic layer was extracted with dichloromethane. The remaining water in the extracted organic layer was removed with MgSO4 and dried. The organic layer was then filtered and concentrated, and the resulting mixture was purified by column chromatography to obtain Compound 1-2 (33 g, 90%).

[0078] 2) Preparation of compounds 1-3 Compound 1-2 (33 g, 76.0 mmol), 380 mL of sulfuric acid (H2SO4), and 380 mL of acetic acid (AcOH) were placed in 3 L of RBF and stirred. Then, N-bromosuccinimide (NBS) (15 g, 83.6 mmol) was added, and the mixture was refluxed at room temperature for 18 hours. After the reaction was complete, the reaction product was added dropwise to water, and the resulting solid was filtered. The resulting solid was then purified by column chromatography to obtain compound 1-3 (33 g, yield: 85%).

[0079] 3) Preparation of compounds 1-4 Compound 1-3 (30.5 g, 59.5 mmol), bis(pinacolate)diborone (19.5 g, 77.3 mmol), Pd(pph3)2Cl2 (2.1 g, 13 mmol), KOAc (12 g, 119 mmol), and 600 mL of 1,4-dioxane were placed in 2 L of RBF and refluxed at 140 °C for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. The remaining water in the extracted organic layer was removed with MgSO4 and dried. The organic layer was then filtered and concentrated, and the resulting mixture was purified by column chromatography to obtain compound 1-4 (28.4 g, 85%).

[0080] 4) Preparation of compounds 1-5 Compound 1-4 (36.4 g, 65 mmol), 2-bromoiodobenzene (37 g, 130 mmol), Pd(PPh3)4 (3.8 g, 3.25 mmol), K2CO3 (18 g, 130 mmol), 520 mL of toluene, 65 mL of EtOH, and 65 mL of H2O were placed in 2 L of RBF and refluxed at 140 °C for 3 days. After the reaction was complete, the reaction mixture was cooled to room temperature and the organic layer was extracted with dichloromethane. The remaining water in the extracted organic layer was removed with MgSO4 and dried. The organic layer was then filtered and concentrated, and the resulting mixture was purified by column chromatography to obtain compound 1-5 (21 g, 54%).

[0081] 5) Preparation of compounds 1-6 Compound 1-5 (21 g, 36 mmol), bis(pinacolate)diborone (13.5 g, 53 mmol), Pd(pph3)2Cl2 (1.3 g, 1.8 mmol), KOAc (7.1 g, 72 mmol), and 360 mL of 1,4-dioxane were placed in 1 L of RBF and refluxed at 140 °C for 3 hours. After the reaction was complete, the mixture was filtered through a Celite filter and the organic layer was concentrated. The mixture was purified by column chromatography to obtain compound 1-6 (10.5 g, 44% yield).

[0082] 6) Preparation of compound C-1 Compound 1-6 (10 g, 16 mmol), Pd2db3 (7.3 g, 8 mmol), S-phos (6.4 g, 16 mmol), NaOt-bu (3.1 g, 32 mmol), and 390 mL of o-xylene were placed in 1 L of RBF and refluxed at 160 °C for 6 hours. After the reaction was complete, the mixture was filtered through a Celite filter and the organic layer was concentrated. The mixture was purified by column chromatography to obtain compound C-1 (1 g, yield: 13%).

[0083] To provide a detailed understanding of this disclosure, the methods and characteristics of organic electroluminescent devices containing the organic electroluminescent compounds of this disclosure are described below.

[0084] [Device Example 1] Manufacturing of an OLED containing the compound according to the present disclosure as a host. An OLED containing the compounds of this disclosure was manufactured. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) of a glass substrate for OLED devices (Geomatec Co., Ltd., Japan) was sequentially ultrasonically cleaned with acetone and isopropyl alcohol, then stored in isopropanol, and used. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Subsequently, compound HI-1 as the first hole injection compound was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 as the first hole transport compound was introduced into another cell. Then, the two materials were evaporated at different rates, and the first hole injection compound was doped with a doping amount of 3 wt% relative to the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer with a thickness of 10 nm. Next, compound HT-1 was deposited to form a first hole transport layer with a thickness of 80 nm on the first hole injection layer. Next, compound HT-2 was placed into another cell of the vacuum deposition apparatus. Subsequently, an electric current was passed through the cell to evaporate the introduced material, thereby forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited on top of them as follows. Each of the host materials listed in Table 1 below was placed as a host in two cells of the vacuum deposition apparatus, and compound D-50 was placed as a dopant in another cell. The two host materials were evaporated in different ratios of 2:1, and the dopants were evaporated simultaneously in different ratios. The dopants were deposited at a doping amount of 10 wt% based on the total amount of host and dopant, forming an emissive layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ETL-1 and EIL-1 were deposited as electron transport materials in a weight ratio of 40:60, forming an electron transport layer with a thickness of 35 nm on the emissive layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm onto the electron transport layer, an 80 nm thick Al cathode was deposited onto the electron injection layer using a separate vacuum deposition apparatus. OLEDs were fabricated in this manner. Each compound was purified by vacuum sublimation under 10⁻⁶ Torre conditions before use.

[0085] [Device Example 2] Manufacturing of an OLED containing the compound according to the present disclosure as a host An OLED was manufactured using the same method as in Device Example 1, except that compound C-1 was used alone as the host material for the light-emitting material.

[0086] [Comparative Example 1] Production of OLEDs containing a conventional compound as a host An OLED was fabricated in the same manner as in Device Example 1, except that a 40 nm thick light-emitting layer was deposited on the second hole transport layer as a light-emitting material, using compound CBP as a host and compound D-50 as a dopant, and a 5 nm thick BAlq was deposited as a hole-blocking layer. Next, ETL-1 and EIL-1 were deposited in a weight ratio of 40:60 to form a 30 nm thick electron transport layer on the hole-blocking layer.

[0087] Table 3 below shows the results for the organic electroluminescent devices of Device Examples 1 and 2 and Comparative Example 1 manufactured as described above, including the driving voltage, luminous efficiency, and emitted color at a brightness of 1,000 nits, as well as the time required for the brightness to decrease from 100% to 95% (lifetime; T95) at a brightness of 20,000 nits.

[0088] [Table 1]

[0089] Referring to Table 1 above, it has been confirmed that organic electroluminescent devices containing the organic electroluminescent compound of this disclosure as a host material exhibit lower drive voltage, higher luminescence efficiency, and longer lifetime characteristics compared to conventional organic electroluminescent devices using a single host material.

[0090] The compounds used in Device Examples 1 and 2 and Comparative Example 1 are shown in Table 2 below.

[0091] [Table 2]

Claims

1. The following equation 1: 【Chemistry 1】 (In the formula, Rings A and B each independently represent substituted or unsubstituted (C6-C30) arylenes; X １ ~X ３ represents N; R ２ represents hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted (C6-C30) aryl; L １ and R ３ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene; L ２ This represents a single bond; Y １ represents -O-, -S-, -R １２ C = CR １２’ -, -R １３ R １４ C - CR １３’ R １４’ -, or -CR １５ R １６ ; R １２ ~R １６ , R １２’ , R １３’ and R １４’ Each of these elements may independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, or may be linked with adjacent substituents to form a ring; m and n each represent an integer of 1 or 2 independently; If m and n are 2 or more, each L １ and L ２ (They may be the same or different.) An organic electroluminescent compound represented by [the specified formula].

2. In formula (1) above 【Chemistry 2】 However, the following equations 1-1 to 1-3, 1-6 and 1-9 to 1-11: 【Transformation 3】 (In the formula, Y １ , R １５ and R １６ This is as defined in claim 1; R4, R5, and R4' are each independently R in claim 1. ２ As defined; a and b each independently represent integers from 1 to 3, e and f each independently represent integers from 1 to 4, a' represents integers from 1 to 5; and If a, b, e, f, and a' are 2 or more, then each of R4', each of R4, and each of R5 may be the same or different. The organic electroluminescent compound according to claim 1, represented by any one of the following.

3. of formula (1) 【Chemistry 4】 However, the following equations 1-14 to 1-17, 1-21 to 1-23, and 1-26 to 1-28: 【Transformation 5】 (In the formula, R4, R5, R4', Y1, a, b, e, f, and a' are as defined in claim 2.) The organic electroluminescent compound according to claim 2, represented by any one of the following.

4. The substituents of the substituted (C1-C30) alkyl, substituted (C6-C30) aryl(ene), and substituted (3-30 member) heteroaryl are deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, and (C6-C30) aryl(ene). Luoxy, (C6-C30)arylthio, unsubstituted or (C6-C30)aryl-substituted (5-30 member) heteroaryl, unsubstituted or (5-30 member) heteroaryl-substituted (C6-C30) aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, amino, mono- or di-(C1- C30) alkylamino, mono- or di-(C2-C30) alkenylamino, (C1-C30) alkyl(C2-C30) alkenylamino, mono- or di-(C6-C30) arylamino, (C1-C30) alkyl(C6-C30) arylamino, mono- or di-(3-30 member) heteroarylamino, (C1-C30) alkyl(3-30 member) heteroarylamino, (C2-C30) alkenyl(C6-C30) arylamino, (C2-C30) alkenyl(3-30 member) heteroarylamino, (C6-C 30) The organic electroluminescent compound according to claim 1, representing at least one selected from the group consisting of aryl (3-30 member) heteroarylamino, (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.

5. The compound represented by formula 1 is the following compound: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 An organic electroluminescent compound according to claim 1, selected from the above.

6. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 1.

7. A plurality of host materials comprising at least one of the organic electroluminescent materials described in claim 6 as a first host material, and at least one of a second host material different from the first host material.

8. The second host material is given by the following formula 12: 【Chemistry 11】 (In the formula, L ａ and L ｂ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar ａ and Ar ｂ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. T １ This represents a single bond; R ９ ~R １２ Each of these independently comprises hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-50 member) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino , represent a substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl (3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl (3-30 member) heteroarylamino, a substituted or unsubstituted mono- or di- (C6-C30) arylamino, a substituted or unsubstituted mono- or di- (3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl (3-30 member) heteroarylamino, or may bond with adjacent substituents to form a ring; f and i each independently represent integers from 1 to 4; g' and h each represent an integer between 1 and 3 independently; If f, g', h, and i are 2 or more, each R ９ , each R １０ , each R １１ and each R １２ (They may be the same or different.) A plurality of host materials according to claim 7, comprising a compound represented by the above.

9. The compound represented by formula 12 is the following compound: 【Chemistry 12】 【Chemistry 13】 A plurality of host materials according to claim 8, selected from the above.

10. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 1.

11. An organic electroluminescent device comprising an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials as described in claim 7.

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