Host materials and organic electroluminescent devices containing same - Patent Application 20070122997

Abstract

Improved host materials are provided that can provide organic electroluminescent devices with higher luminous efficiency and / or longer lifetime characteristics. The present invention relates to a plurality of host materials including a first host material containing a compound represented by any one of Formulas 1 to 4 and a second host material containing a compound represented by a specific formula, and an organic electroluminescent device including the same. By including a specific combination of compounds as the host material, it is possible to provide a device with excellent luminous efficiency and / or life characteristics. TIFF2026041993000058.tif62170

Description

[Technical Field]

[0001] The present disclosure relates to host materials comprising specific combinations of compounds and organic electroluminescent devices containing the same. [Background technology]

[0002] Electroluminescent (EL) devices are self-emitting devices that have the advantages of providing a wider viewing angle, a larger contrast ratio, and a faster response time. In 1987, Eastman Kodak developed the first organic EL device by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] Organic electroluminescent devices (OLEDs) convert electrical energy into light by applying electricity to organic electroluminescent materials and typically include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of an OLED may optionally include a hole injection layer, a hole transport layer, a hole auxiliary layer, an emitting auxiliary layer, an electron blocking layer, an emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Materials used in the organic layers can be classified according to their functions into hole injection materials, hole transport materials, hole auxiliary materials, emitting auxiliary materials, electron blocking materials, emitting material layers (including host and dopant materials), electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. In an OLED, application of a voltage causes holes from the anode and electrons from the cathode to be injected into the emitting layer, and recombination of the holes and electrons generates high-energy excitons. When the organic light-emitting compound returns from an excited state to a ground state, the organic light-emitting compound is excited by energy and emits light from the energy.

[0004] The most important factor determining the luminous efficiency of an OLED is the luminescent material. The luminescent material must have the following characteristics: high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed luminescent material layer. Luminescent materials are classified into blue, green, and red luminescent materials based on the luminescent color, and also include yellow and orange luminescent materials. Furthermore, luminescent materials are further classified into host materials and dopant materials based on their functions. Recently, the development of OLEDs with high efficiency and long lifetimes has become an urgent issue. In particular, considering the EL characteristics required for medium- and large-sized OLED panels, the development of luminescent materials superior to conventional materials is urgently needed. To this end, the host material, which serves as a solvent and energy transfer material in the solid state, must have high purity and a suitable molecular weight for deposition under vacuum. Furthermore, the host material must have a high glass transition temperature and thermal decomposition temperature to achieve thermal stability, high electrochemical stability to achieve a long lifetime, easy formability of an amorphous thin film, good adhesion to adjacent layers, and no interlayer migration. Summary of the Invention [Problem to be solved by the invention]

[0005] It is an object of the present disclosure to provide improved host materials that can provide organic electroluminescent devices with higher luminous efficiency and / or longer lifetime properties. [Means for solving the problem]

[0006] The present inventors have discovered that the above object can be achieved by providing a plurality of host materials including a first host material and a second host material, wherein the first host material includes a compound represented by the following Formula 1, and the second host material includes a compound represented by the following Formula 2: [ka] (In the formula, Ar1 to Ar3 each independently represent 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) 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, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1 to C30) alkylene, a substituted or unsubstituted (C6 to C30) arylene, a substituted or unsubstituted (3 to 30-membered) heteroarylene, or a substituted or unsubstituted (C3 to C30) cycloalkylene; However, all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen), and [ka] (In the formula, X is -N=, -NR 15 represents -, -O- or -S-; Z = -N, -NR 16 -, -O- or -S-, provided that when X represents -N=, Z is -NR 16 -, -O-, or -S-, and X is -NR 15 -, Z represents -N=, -O- or -S-; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; R 11 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R 12 ~R14 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or R 12 ~R 14 adjacent ones of can be joined to each other to form a ring, R 15 and R 16 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; L represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; a' represents an integer of 1, b' and c' each independently represent an integer of 1 or 2, d' represents an integer of 1 to 4, and when b', c', and d' each independently represent an integer of 2 or more, R2 to R 14 may be the same or different) It has been found that this can be achieved by

[0007] Effect of the invention By including a specific combination of compounds of the present disclosure as a host material, it is possible to provide an organic electroluminescent device having higher luminous efficiency and / or longer life characteristics than conventional organic electroluminescent devices, and to manufacture a display device or lighting device using the same. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0009] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and can include at least one compound. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0010] The term "multiple organic electroluminescent materials" in the present disclosure refers to an organic electroluminescent material including a combination of at least two compounds that can be included in any organic layer constituting an organic electroluminescent device. It can refer to both the material before being included in the organic electroluminescent device (e.g., before deposition) and the material after being included in the organic electroluminescent device (e.g., after deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds that can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be included in the same layer or different layers by methods used in the art; for example, they can be mixed and evaporated or co-evaporated, or can be evaporated separately.

[0011] The term "multiple host materials" in the present disclosure refers to a host material that includes a combination of at least two compounds and can be included in any light-emitting layer constituting an organic electroluminescent device. It can refer to both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple host materials of the present disclosure can be a combination of two or more host materials, and can optionally further include conventional materials included in organic electroluminescent materials. The two or more compounds included in the multiple host materials of the present disclosure can be included in one light-emitting layer, or can be included in different light-emitting layers. For example, the two or more host materials can be mixed and evaporated or co-evaporated, or can be evaporated separately.

[0012] As used herein, the term "(C1-C30) alkyl" refers to a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 10, more preferably 1 to 6 carbon atoms. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term "(C3-C30) cycloalkyl" or "(C3-C30) cycloalkylene" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7 carbon atoms. The cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocycloalkyl" refers to a cycloalkyl having 3 to 7 ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The term "(C6-C30)aryl" or "(C6-C30)arylene" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms. The aryl or arylene may be partially saturated and may include a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, etc. The term "(3- to 30-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" refers to an aryl or arylene having 3 to 30 skeletal ring atoms, preferably 5 to 30 skeletal ring carbon 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 heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, as well as fused-ring heteroaryls such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, and the like. Furthermore, "halogen" includes F, Cl, Br and I.

[0013] As used herein, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group, i.e., a substituent. In the present disclosure, the substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, or substituted alkylarylamino are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, methyl ... (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3-30 membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl and / or (3-30 membered)heteroaryl, unsubstituted (C6-C30)aryl substituted with at least one of (C1-C30)alkyl, (C6-C30)aryl and (3-30 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, unsubstituted or (C1-C30)alkyl-substituted mono- or di-(C6-C3 0) At least one selected from the group consisting of arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of (C1-C20) alkyl, (C6-C25) aryl unsubstituted or substituted with (C1-C10) alkyl and / or (C6-C18) aryl, (3-25 membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl, di(C6-C18) arylamino, and (C1-C6) alkyl(C6-C25) aryl. For example, the substituents are each independently at least one of methyl, phenyl, naphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl substituted with phenyl, benzocarbazolyl substituted with phenyl, benzonaphthothiophenyl, and diphenylamino.

[0014] In the formulas of the present disclosure, a ring formed by the bonding of adjacent substituents means that at least two adjacent substituents are bonded or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic or aromatic ring or a combination thereof, preferably a substituted or unsubstituted monocyclic or polycyclic (3-26 membered) alicyclic or aromatic ring or a combination thereof, more preferably an unsubstituted or alkyl-substituted monocyclic or polycyclic (5-10 membered) aromatic ring, such as a benzene ring, a methyl-substituted indene ring, or a benzothiophene ring. The formed ring may also contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.

[0015] As used herein, heteroaryl, heteroarylene, and heterocycloalkyl may each independently 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, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0016] In Formula 1, Ar1 to Ar3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C 30) 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, or substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino. According to one embodiment of the present disclosure, Ar1 to Ar3 each independently represent a substituted or unsubstituted (C6-C29) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl. According to another embodiment of the present disclosure, Ar1 to Ar3 each independently represent unsubstituted or (C1-C10) alkyl and / or (C6-C18) aryl-substituted (C6-C29) aryl, or unsubstituted or (C6-C18) aryl-substituted (5-30 membered) heteroaryl. Specifically, Ar1 may represent dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, unsubstituted or biphenyl-substituted carbazolyl, unsubstituted or phenyl- and / or biphenyl-substituted benzocarbazolyl, dibenzocarbazolyl, or unsubstituted or phenyl-substituted (20-30 membered) heteroaryl containing at least one of N, O, and S, and Ar2 and Ar3 may each independently represent phenyl, naphthalene, biphenyl, terphenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, phenyl-substituted carbazolyl, or phenyl-substituted benzocarbazolyl.

[0017] L1 to L3 each independently represent a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-30 membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L1 to L3 each independently represent a single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (3-29 membered) heteroarylene. According to another embodiment of the present disclosure, L1 to L3 each independently represent a single bond, unsubstituted (C6-C18) arylene or unsubstituted nitrogen-containing (5-26 membered) heteroarylene substituted with at least one of (C1-C6) alkyl, (C6-C18) aryl, and di(C6-C18) arylamino. Specifically, L1 to L3 may each independently represent a single bond, unsubstituted or diphenylamino-substituted phenylene, naphthylene, phenylnaphthylene, naphthylphenylene, biphenylene, dimethylfluorenylene, or nitrogen-containing (26-membered) heteroarylene.

[0018] According to one embodiment of the present disclosure, Formula 1 can be represented by at least one of the following Formulas 1-1 to 1-14. [ka] [ka] [ka] [ka]

[0019] In formulas 1-1 to 1-14, Ar2, Ar3, and L1 to L3 are as defined in formula 1, and the definitions of other substituents are as follows.

[0020] Y represents CR7R8, NR9, O or S.

[0021] T1~T 13 and X1~X 12 each independently represents N or CV1, preferably CV1.

[0022] V1 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, or two adjacent V's may be bonded to each other to form a ring. According to one embodiment of the present disclosure, each V independently represents hydrogen or a substituted or unsubstituted (C6-C25)aryl, or two adjacent V's may be bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic or aromatic ring, or a combination thereof, and the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P. According to another embodiment of the present disclosure, each V independently represents hydrogen or unsubstituted (C6-C18) aryl, or two adjacent Vs can be bonded or fused to each other to form an unsubstituted monocyclic (3-10 membered) alicyclic or aromatic ring. For example, each V independently represents hydrogen or phenyl, or two adjacent Vs can be bonded or fused to each other to form a benzene ring.

[0023] L4 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L4 represents a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L4 represents a single bond or an unsubstituted (C6-C18) arylene. For example, L4 may represent a single bond or phenylene.

[0024] P1 and P2 each independently represent a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl. P1 and P2 may be the same or different, and preferably the same. According to one embodiment of the present disclosure, P1 and P2 each independently represent a substituted or unsubstituted (C1-C20) alkyl or a substituted or unsubstituted (C6-C25) aryl. According to another embodiment of the present disclosure, P1 and P2 each independently represent an unsubstituted (C1-C10) alkyl or an unsubstituted (C6-C18) aryl. Specifically, P1 and P2 may each independently represent methyl or phenyl.

[0025] R2 to R9 and P3 to P5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to 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, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or adjacent ones of R2 to R9 and P3 to P5 can be bonded to each other to form a ring. R7 and R8 can be the same or different, and are preferably the same. According to one embodiment of the present disclosure, R2 to R9 and P3 to P5 each independently represent hydrogen, substituted or unsubstituted (C1-C20) alkyl, or substituted or unsubstituted (C6-C25) aryl, or adjacent ones of R2 to R9 and P3 to P5 can be bonded or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic or aromatic ring, or a combination thereof, and the formed ring can contain at least one heteroatom selected from B, N, O, S, Si, and P. According to another embodiment of the present disclosure, R2 to R9 and P3 to P5 each independently represent hydrogen, unsubstituted (C1-C10) alkyl, or unsubstituted (C6-C18) aryl, or adjacent ones of R2 to R9 and P3 to P5 can be bonded or fused to each other to form an unsubstituted or alkyl-substituted monocyclic or polycyclic (5-10 membered) ring.For example, R2, R3, R6 and P3 may each independently represent hydrogen, or adjacent ones of R2, R3, R6 and P3 may be bonded to each other to form a benzene ring, R4 may represent hydrogen or may be bonded to adjacent substituents to form a benzene ring, a methyl-substituted indene ring or a benzothiophene ring, R5, P4 and P5 may each independently represent hydrogen, R7 and R8 may represent methyl, and R9 may represent phenyl.

[0026] Ar4 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl. According to one embodiment of the present disclosure, Ar4 represents substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-25 membered) heteroaryl. According to another embodiment of the present disclosure, Ar4 represents unsubstituted (C6-C18) aryl. Specifically, Ar4 may represent phenyl or biphenyl.

[0027] Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment of the present disclosure, Ar5 and Ar6 each independently represent an unsubstituted (C6-C18) aryl. For example, Ar5 and Ar6 each independently may represent a phenyl.

[0028] b, c, d, f, and g each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, c" and h each independently represent an integer of 1 to 3, and i represents an integer of 1 to 5; when b to i and c" each independently represent an integer of 2 or greater, R2 to R6 and P3 to P5 may be the same or different.

[0029] In Equation 2, X is -N=, -NR 15 represents -, -O- or -S-, and Z represents -N=, -NR 16 -, -O- or -S-, provided that when X represents -N=, Z is -NR 16 -, -O-, or -S-, and X is -NR 15 When X represents -, Z represents -N=, -O- or -S-. According to one embodiment of the present disclosure, X represents -N=, -NR 15 Z represents -, -O- or -S-, and Z represents -N=, -NR 16 represents -, -O-, or -S-, provided that either X or Z represents -N=.

[0030] In Formula 2, HAr represents a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (3-25 membered) heteroaryl. According to another embodiment of the present disclosure, HAr represents a (5-20 membered) heteroaryl substituted with a (C6-C30) aryl and / or a (3-25 membered) heteroaryl. Specifically, HAr may represent a substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted triazinyl, or substituted or unsubstituted pyrimidinyl. For example, HAr may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted quinoxalinyl, or a substituted quinazolinyl, wherein the substituents of the substituted triazinyl, the substituted pyrimidinyl, the substituted quinoxalinyl, and the substituted quinazolinyl may be at least one of phenyl, biphenyl, naphthyl, spirobifluorenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, phenyl-substituted carbazolyl, and phenyl-substituted benzocarbazolyl.

[0031] In Equation 2, R 11 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl. 11represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-25 membered) heteroaryl. According to another embodiment of the present disclosure, R 11 represents unsubstituted or (C1-C10) alkyl and / or (C6-C18) aryl-substituted (C6-C29) aryl, or unsubstituted or (C6-C18) aryl-substituted (5-25 membered) heteroaryl. 11 may represent phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, spiro[fluorene-benzofluoren]yl, phenyl-substituted carbazolyl, phenyl-substituted benzocarbazolyl, dibenzofuranyl, or dibenzothiophenyl.

[0032] In Equation 2, R 12 ~R 14 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or R 12 ~R 14 Adjacent groups can be joined together to form a ring. For example, R 12 ~R 14 may each independently represent hydrogen.

[0033] In Equation 2, R 15 and R 16each 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) 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, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. According to one embodiment of the present disclosure, R 15 and R 16 each independently represents a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (3-25 membered) heteroaryl. 15 and R 16 Each independently represents an unsubstituted (C6-C18) aryl. For example, R 15 may represent phenyl or biphenyl, R 16 may represent phenyl.

[0034] In Formula 2, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L represents a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L represents a single bond or an unsubstituted (C6-C18) arylene. Specifically, L may represent a single bond, phenylene, or biphenylene.

[0035] In Formula 2, a' represents an integer of 1, b' and c' each independently represent an integer of 1 or 2, d' represents an integer of 1 to 4, and when b', c', and d' each independently represent an integer of 2 or more, R2 to R 14Each of may be the same or different.

[0036] According to one embodiment of the present disclosure, Formula 2 can be represented by at least one of the following Formulas 2-1 to 2-6. [ka]

[0037] In formulas 2-1 to 2-6, HAr and R 11 ~R 16 , L and a′ to d′ are as defined in Formula 2.

[0038] Compounds represented by formula 1 can be specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0039] Compounds represented by formula 2 can be specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka]

[0040] A combination of at least one of the compounds C-1-1 to C-1-195 and at least one of the compounds C-2-1 to C-2-112 can be used in an organic electroluminescent device.

[0041] The compounds represented by Formulas 1 and 2 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to the following Reaction Schemes 1 to 3 and Korean Patent Application Publication Nos. 10-2013-0106255A (published September 27, 2013), 10-2012-0042633A (published May 3, 2012), 10-2018-0099510A (published September 5, 2018), and 10-2015-0066202A (published June 16, 2015), and the compound represented by Formula 2 can be prepared by referring to, but not limited to, Korean Patent Application Publication No. 10-2017-0051198A (published May 11, 2017).

[0042] [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka]

[0043] In Reaction Schemes 1 to 3, T1 to T 13 , X1~X 12 , L1 to L3, Ar2 and Ar3 are as defined in formulas 1 to 4 and 1 to 7 above.

[0044] An organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may include multiple organic electroluminescent materials, where the compound represented by Formula 1 is included as a first organic electroluminescent material and the compound represented by Formula 2 is included as a second organic electroluminescent material. According to one embodiment of the present disclosure, the organic electroluminescent device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, where the light-emitting layer includes multiple host materials, including the compound represented by Formula 1 as a first host material and the compound represented by Formula 2 as a second host material.

[0045] The light-emitting layer includes a host and a dopant. The host includes multiple host materials. The multiple host materials include a first host material and a second host material. The first host material may consist solely of a compound represented by Formula 1 or at least one compound represented by Formula 1, and may further include a conventional material contained in an organic electroluminescent material. The second host material may consist solely of a compound represented by Formula 2 or at least one compound represented by Formula 2, and may further include a conventional material contained in an organic electroluminescent material. The weight ratio of the first host compound to the second host compound is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0046] The light-emitting layer is a layer that emits light, and can be a single layer or a multi-layer structure in which two or more layers are stacked. In the multiple host materials according to the present disclosure, the first and second host materials can be both included in one layer, or can be included in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer is less than about 20% by weight.

[0047] The organic electroluminescent device of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device may further include an amine-based compound as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the emission material, the emission auxiliary material, and the electron blocking material, in addition to the plurality of host materials of the present disclosure. Also, according to one embodiment of the present disclosure, the organic electroluminescent device may further include an azine-based compound as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material, in addition to the plurality of host materials of the present disclosure.

[0048] The dopant that is included in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably phosphorescent dopant.The phosphorescent dopant material that is applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) metallized complex compound, preferably can be selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) ortho-metallized complex compound, more preferably can be selected from ortho-metallized iridium complex compound.

[0049] The dopant may include, but is not limited to, a compound represented by at least one of the following formulas 101-103: [ka]

[0050] In Formulas 101-103, L is selected from the following structures 1 and 2: [ka] is selected from.

[0051] R 100 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; R 101 ~R 109 and R 111 ~R 123 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or an adjacent R 101 ~R 109 and R 111 ~R 123 can be bonded to form a ring. Specifically, R 106 ~R 109 is the adjacent R 106 ~R 109 and can be combined to form a ring, such as an unsubstituted or alkyl-substituted indene ring, an unsubstituted or alkyl-substituted benzothiophene ring, or an unsubstituted or alkyl-substituted benzofuran ring; R 120 ~R 123 is the adjacent R 120 ~R 123 can be combined with R to form a ring, for example, 120 and R 121 can be bonded to each other to form an unsubstituted or alkyl-substituted benzene ring, an unsubstituted or alkyl-substituted fluorene ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0052] R 124 ~R127 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, or the adjacent R 124 ~R 127 and can be combined to form a ring, such as an unsubstituted or alkyl-substituted indene ring, an unsubstituted or alkyl-substituted benzothiophene ring, or an unsubstituted or alkyl-substituted benzofuran ring; R 201 ~R 211 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium- and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or unsubstituted or alkyl- and / or deuterium-substituted (C6-C30) aryl, or an adjacent R 201 ~R 211 and can be bonded to form a ring, for example, an unsubstituted or alkyl-substituted indene ring, an unsubstituted or alkyl-substituted benzothiophene ring, or an unsubstituted or alkyl-substituted benzofuran ring, and each r independently represents an integer of 1 to 3. When each r independently represents an integer of 2 or more, R 100 may be the same or different, and n represents an integer from 1 to 3.

[0053] Specific examples of the dopant compound include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka]

[0054] In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, can be used between the anode and the light-emitting layer. The hole injection layer can be a multilayer structure to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayer structures can simultaneously use two compounds. The hole transport layer or the electron blocking layer can also be a multilayer structure.

[0055] In addition, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, and each of the multilayered layers can use two compounds simultaneously. Also, the hole blocking layer or the electron transport layer can be multilayered, and each of the multilayered layers can use multiple compounds.

[0056] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum deposition, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods can be used.

[0057] When a solvent is used in the wet film-forming method, a thin film can be formed by dissolving or diffusing the materials for forming each layer in any appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent as long as it can dissolve or diffuse the materials for forming each layer and does not cause any problems in film-forming ability.

[0058] In addition, the first host compound and the second host compound can generally be formed into a film by the above method through a co-evaporation process or a mixed-evaporation process. Co-evaporation is a mixed vapor deposition method in which two or more materials are placed in separate crucible sources and current is passed through both cells simultaneously to evaporate the materials. Mixed vapor deposition is a mixed vapor deposition method in which two or more materials are mixed in one crucible source before evaporating them and current is passed through the cells to evaporate the materials. Also, when the first and second host compounds are present in the same layer or different layers of an organic electroluminescent device, the two host compounds can be vapor-deposited separately. For example, the first host compound can be vapor-deposited, and then the second host compound can be vapor-deposited.

[0059] The present disclosure may provide a display device by using a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display device or a lighting device can be manufactured by using a plurality of host materials of the present disclosure. Specifically, a display device, for example, a display device for a smartphone, tablet, notebook, PC, TV, or car, or a lighting device, for example, an outdoor or indoor lighting device, can be manufactured by using a plurality of host materials of the present disclosure.

[0060] The preparation method and physical properties of the compound of the present disclosure and the physical properties of the OLED of the present disclosure will be described in detail below.However, the following examples only show the preparation method of the compound of the present disclosure and the physical properties of the OLED in detail, and the present disclosure is not limited to the following examples. [Example]

[0061] Example 1: Synthesis of Compound C-2-95 [ka] In a reaction vessel, 4.0 g of compound A (CAS: 2085325-18-2, 9.5 mmol), 2.8 g of 2-chloro-3-phenylquinoxaline (11.4 mmol), 0.5 g of tetrakis(triphenylphosphine)palladium (PPh3)4) (0.5 mmol), and 2.0 g of potassium carbonate (K2CO3) (19 mmol) were added to 30 mL of toluene, 7 mL of EtOH, and 10 mL of water, and the mixture was stirred under reflux for 1 day. After completion of the reaction, the reaction mixture was cooled to room temperature and then filtered through Celite with methylene chloride (MC). The filtrate was distilled under reduced pressure and then separated by column chromatography using methylene chloride / hexane (MC / Hex) to obtain 2.7 g of compound C-2-95 (yield: 57%).

[0062] [Table 1]

[0063] Example 2: Synthesis of Compound C-2-112 [ka] 23.8 g of compound A (56.6 mmol), 15.0 g of 2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (47.2 mmol), 2.72 g of Pd(PPh3)4 (2.36 mmol), and 16.3 g of K2CO3 (118 mmol) were added to 240 mL of toluene, 60 mL of EtOH, and 60 mL of purified water, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then filtered through silica gel. The organic layer was distilled under reduced pressure and then recrystallized from toluene to obtain 13.8 g of compound C-2-112 (yield: 51%).

[0064] [Table 2]

[0065] Example 3: Synthesis of Compound C-2-105 [ka] 4.0 g of compound A (9.5 mmol), 3.9 g of 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.4 mmol), 0.5 g of Pd(PPh3)4 (0.5 mmol), and 2.6 g of K2CO3 (19 mmol) were added to 30 mL of toluene, 7 mL of EtOH, and 10 mL of purified water, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, stirred at room temperature, and then MeOH was added. The resulting solid was filtered under reduced pressure and then separated by column chromatography using MC to obtain 4.6 g of compound C-2-105 (yield: 80%).

[0066] [Table 3]

[0067] Example 4: Synthesis of Compound C-2-93 [ka] 3.0 g of compound A (7.1 mmol), 3.4 g of 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (9.26 mmol), 0.4 g of Pd(PPh3)4 (0.36 mmol), and 2.0 g of K2CO3 (14 mmol) were added to 36 mL of toluene, 8 mL of EtOH, and 12 mL of purified water, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, stirred at room temperature, and then MeOH was added. The resulting solid was filtered under reduced pressure and then separated by column chromatography using MC to obtain 3.3 g of compound C-2-93 (yield: 75%).

[0068] [Table 4]

[0069] Example 5: Synthesis of Compound C-2-94 [ka] 4.0 g of compound A (9.5 mmol), 3.6 g of 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (11.4 mmol), 0.5 g of Pd(PPh3)4 (0.5 mmol), and 2.6 g of K2CO3 (19 mmol) were added to 30 mL of toluene, 7 mL of EtOH, and 10 mL of purified water, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, stirred at room temperature, and then MeOH was added. The resulting solid was filtered under reduced pressure and then separated by column chromatography using MC to obtain 3.45 g of compound C-2-94 (yield: 63%).

[0070] [Table 5]

[0071] Example 6: Synthesis of compound C-1-138 [ka] 5.0 g of compound B (11.2 mmol), 3.0 g of N-phenyl-[1,1'-biphenyl]-4-amine (12.3 mmol), 0.5 g of Pd2(dba)3 (0.56 mmol), 0.46 g of esphos (1.12 mmol), and 2.7 g of NaOtBu (28 mmol) were added to 60 mL of toluene, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, stirred at room temperature, and then MeOH was added to it. The resulting solid was filtered under reduced pressure and then separated by column chromatography using MC / Hex to obtain 2.3 g of compound C-1-138 (yield: 34%).

[0072] [Table 6]

[0073] Example 7: Synthesis of compound C-1-159 [ka] 5.0 g of compound C (15.2 mmol), 5.4 g of 4-bromo-N,N-diphenylaniline (16.7 mmol), 0.7 g of Pd2(dba)3 (0.76 mmol), 0.6 g of Esphos (1.52 mmol), and 2.9 g of NaOtBu (30.4 mmol) were added to 80 mL of o-xylene, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, stirred at room temperature, and then MeOH was added to it. The resulting solid was filtered under reduced pressure and then separated by column chromatography using MC / Hex to obtain 4.0 g of compound C-1-159 (yield: 46%).

[0074] [Table 7]

[0075] Example 8: Synthesis of compound C-1-141 [ka] 1) Synthesis of Compound E In a reaction vessel, 10.0 g of compound D (34.3 mmol), 14.6 g of 1-bromo-4-iodobenzene (51.5 mmol), 3.28 g of CuI (17.2 mmol), 4.12 g of EDA (68.6 mmol), and 14.6 g of KPO (68.6 mmol) were added to 170 mL of toluene, and the mixture was stirred under reflux at 145 °C for 3 hours. After completion of the reaction, the reaction mixture was extracted with MC and then dried over MgSO. The residue was separated by column chromatography, and MeOH was then added to it. The resulting solid was filtered under reduced pressure to obtain 9.0 g of compound E (yield: 59%).

[0076] 2) Synthesis of Compound C-1-141 In a reaction vessel, 5.0 g of compound E (11 mmol), 3.3 g of N-phenyl-[1,1'-biphenyl]-4-amine (13 mmol), 0.513 g of Pd2(dba)3 (0.56 mmol), 0.460 g of esphos (1 mmol), and 2.691 g of NaOt-Bu (28 mmol) were added to 60 mL of toluene, and the mixture was stirred under reflux at 100 °C for 0.5 hours. After completion of the reaction, the reaction mixture was extracted with MC and then dried over MgSO4. The residue was separated by column chromatography, and then MeOH was added to it. The resulting solid was filtered under reduced pressure to obtain 1.3 g of compound C-1-141 (yield: 19%).

[0077] [Table 8]

[0078] Example 9: Synthesis of Compound C-1-195 [ka] 1) Synthesis of Compound F 15.0 g of compound D (51.5 mmol), 29.3 g of 1-bromo-3-iodobenzene (103 mmol), 4.9 g of CuI (25.8 mmol), 7.0 mL of ethylenediamine (103 mmol), and 27.5 g of KPO (129 mmol) were added to 250 mL of toluene, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then filtered through silica gel. The organic layer was concentrated and then recrystallized with EA to give 14.2 g of compound F (yield: 62%).

[0079] 2) Synthesis of Compound C-1-195 14.0 g of compound F (31.4 mmol), 7.78 g of N-phenyl-[1,1'-biphenyl]-3-amine (31.7 mmol), 1.44 g of Pd2dba3 (1.57 mmol), 635 mg of t-Bu3P (3.14 mmol), and 6.04 g of t-BuONa (62.8 mmol) were added to 160 mL of toluene, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with distilled water and EA. The organic layer was distilled under reduced pressure and then separated by column chromatography using MC / Hex to obtain 14.6 g of compound C-1-195 (yield: 76%).

[0080] [Table 9]

[0081] Device Examples 1-1 to 1-7: Fabrication of OLEDs According to the Present Disclosure An OLED according to the present disclosure was fabricated as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for OLED (Geomatec Co., Ltd., Japan) was ultrasonically cleaned with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate was attached to a substrate holder in a vacuum evaporation system. Compound HI-1 was introduced into the cell of the vacuum evaporation system, and the pressure in the chamber of the system was then increased to 10 -6The pressure was controlled at 500 kPa (1.2 MPa). A current was then applied to the cell to evaporate the introduced material, thereby forming an 80-nm-thick first hole-injection layer on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum evaporation system, and a current was applied to the cell to evaporate it, thereby forming a 5-nm-thick second hole-injection layer on the first hole-injection layer. Next, compound HT-1 was introduced into another cell of the vacuum evaporation system, and a current was applied to the cell to evaporate it, thereby forming a 10-nm-thick first hole-transport layer on the second hole-injection layer. Next, compound HT-2 was introduced into another cell of the vacuum evaporation system, and a current was applied to the cell to evaporate it, thereby forming a 60-nm-thick second hole-transport layer on the first hole-transport layer. After forming the hole injection layer and hole transport layer, an emitting layer was formed thereon as follows: the first host compound and the second host compound shown in Table 1 were introduced into two cells of a vacuum evaporation system as hosts, respectively, and compound D-71 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, and simultaneously the dopant material was evaporated in a different ratio to form a 40 nm-thick emitting layer in the second hole transport layer with a doping amount of 3 wt % based on the total amount of host and dopant. Next, compounds ET-1 and EI-1 were evaporated in two other cells in a 1:1 ratio to form a 35 nm-thick electron transport layer in the emitting layer. Compound EI-1 was then deposited as a 2 nm-thick electron injection layer in the electron transport layer, and an 80 nm-thick Al cathode was deposited on the electron injection layer using another vacuum evaporation system. Thus, an OLED was fabricated. [ka]

[0082] Comparative Examples 1-7: Fabrication of OLEDs not according to the present disclosure The OLED was fabricated in the same manner as Device Example 1-1, except that only the second host compound shown in Table 1 was used instead of the two hosts.

[0083] The luminous efficiency at a luminance of 5,000 nits and the time it took for the luminance to decrease from an initial 100% to 96% (T96) at a constant current at a luminance of 5,000 nits for the OLEDs fabricated in the device examples and comparative examples are shown in Table 1 below.

[0084] [Table 10]

[0085] [Table 11]

[0086] Device Examples 8-15: Fabrication of OLEDs According to the Present Disclosure OLEDs were fabricated in the same manner as in Device Example 1-1, except that the first host compound and the second host compound shown in Table 2 were used. The luminous efficiency at a luminance of 1,000 nits and the time (T95) required for the luminance to decrease from an initial 100% to 95% at a constant current at a luminance of 5,000 nits for the OLEDs fabricated in the device examples are shown in Table 2 below.

[0087] [Table 12]

[0088] In Tables 1 and 2, the compounds used as the first host and the second host are the same as the compounds exemplified as specific compounds in this specification.From the above device examples and comparative examples, it has been confirmed that the organic electroluminescent device according to the present disclosure has a higher luminous efficiency of at least 17.5% and an improved lifespan of at least 100 hours compared with conventional organic electroluminescent devices.

Claims

1. a plurality of host materials including a first host material and a second host material, The first host material has the following formula 1-4: 【Chemistry 1】 (In the formula, Ar ２ and Ar ３ each independently represent 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) 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, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; L １ ~L ３ each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; However, L １ ~L ３ are all single bonds, and Ar ２ and Ar ３ are all hydrogen, T １ ~T １３ are each independently N or CV １ represents V １ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or two adjacent V １ can be bonded to each other to form a ring) and The second host material has the following formula 2: 【Chemistry 2】 (In the formula, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl; R １１ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R １２ ~R １４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, or R １２ ~R １４ adjacent ones of can be joined to each other to form a ring, L represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; a' represents an integer of 1, b' and c' each independently represent an integer of 1 or 2, d' represents an integer of 1 to 4, and when b', c', and d' each independently represent an integer of 2 or more, R １２ ~R １４ may be the same or different) A plurality of host materials comprising a compound represented by:

2. Ar ２ 、Ar ３ 、 １ ~L ３ 、HAr、R １１ ~R １４ and the substituent of the substituted alkyl, the substituted alkylene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino or the substituted alkylarylamino in L is each independently being substituted with deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or substituted with (C6-C30) aryl. (3- to 30-membered) heteroaryl, unsubstituted or (3- to 30-membered) 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, amino, mono- or di-(C1-C30) alkylamino, unsubstituted or (C1-C30) alkyl-substituted mono- or di-(C6-C30) arylamino, (C1-C30) 10. The plurality of host materials of claim 1, wherein the at least one of the (C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

3. The compounds represented by formula 1-4 are the following compounds: 【Transformation 3】 【Chemistry 4】 【Transformation 5】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from the group consisting of:

4. The compound represented by formula 2-1 is the following compound: 【Transformation 6】 10. The plurality of host materials of claim 1, wherein the host material is at least one selected from the group consisting of:

5. 10. 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 according to claim 1.

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