Multiple host materials and organic electroluminescent devices comprising the same

Abstract

The present disclosure relates to a plurality of host materials, the plurality of host materials including a first host material and a second host material, the first host material including a compound represented by Formula 1, the second host material including a compound represented by Formula 2, and an organic electroluminescent device including the plurality of host materials. By including a specific combination of the compounds of the present disclosure as host materials, an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics compared to conventional organic electroluminescent devices can be provided.

Description

Technical Field

[0001] The present disclosure relates to a host material comprising a combination of specific compounds, and an organic electroluminescent device comprising the host material. Background Art

[0002] An electroluminescent (EL) device is a self-luminous device, and it has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The organic EL device was first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and an aluminum complex as materials for forming a light-emitting layer [Appl. Phys. Lett. [Applied Physics Letters] 51, 913, 1987].

[0003] An organic electroluminescent device (OLED) converts electrical energy into light by applying an electric power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. If necessary, the organic layer of the OLED may include a hole injection layer, a hole transport layer, a hole assist layer, a light-emission assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the organic layer can be classified into a hole injection material, a hole transport material, a hole assist material, a light-emission assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. In the OLED, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by the recombination of the holes and the electrons. The organic light-emitting compound emits light by the energy moving to an excited state and the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0004] The most important factor determining the luminous efficiency in OLEDs is the luminescent material. The luminescent material is required to have the following characteristics: high quantum efficiency, high electron and hole mobilities, and uniformity and stability of the formed luminescent material layer. The luminescent materials are classified into blue, green, and red luminescent materials according to the emission color, and further include yellow or orange luminescent materials. In addition, in terms of function, the luminescent materials are classified into host materials and dopant materials. Recently, the urgent task is to develop OLEDs with high efficiency and long lifetime. Specifically, considering the EL characteristics required for medium and large OLED panels, there is an urgent need to develop highly excellent luminescent materials superior to conventional materials. For this purpose, preferably, as a solid-state solvent and energy emitter, the host material should have high purity and a suitable molecular weight for deposition under vacuum. In addition, the host material is required to have a high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve long lifetime, easy formability of an amorphous thin film, good adhesion to adjacent layers, and immobility between layers. SUMMARY OF THE INVENTION

[0005] TECHNICAL PROBLEM

[0006] An object of the present disclosure is to provide an improved host material capable of providing an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics.

[0007] SOLUTION TO THE PROBLEM

[0008] The present inventors have found that the above object can be achieved by a plurality of host materials including a first host material and a second host material, wherein the first host material contains a compound represented by Formula 1, and the second host material includes a compound represented by Formula 2:

[0009]

[0010] Wherein,

[0011] Ar1 to Ar3 each independently represent hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;

[0012] L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;

[0013] Provided that, except for the case where all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen; and

[0014]

[0015] Wherein,

[0016] X represents -N=, -NR15-, -O- or -S-;

[0017] Z represents -N=, -NR 16 -, -O- or -S-; provided that when X represents -N=, Z represents -NR 16 -, -O- or -S-, and when X represents -NR 15 -, Z represents -N=, -O- or -S-;

[0018] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0019] R 11 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0020] R 12 to R 14Each independently represents hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or R 12 to R 14 Those adjacent among them can be connected to each other to form one or more rings;

[0021] R 15 and R 16 Each independently represents hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;

[0022] L represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group;

[0023] 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; wherein if b′, c′, and d′ are each independently 2 or greater integers, then R 12 to R 14 Each of them can be the same or different.

[0024] Advantages of the present invention

[0025] By including a specific combination of the compounds of the present disclosure as a host material, an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics compared to a conventional organic electroluminescent device can be provided, and a display system or a lighting system using the organic electroluminescent device is manufactured. Detailed Description

[0026] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and does not mean to limit the scope of the present disclosure in any way.

[0027] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. When necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a luminescence assisting material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0028] The term "a plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material containing a combination of at least two compounds, and the material can be included in any organic layer constituting the 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 plurality of organic electroluminescent materials can be a combination of at least two compounds, and these materials can be included in at least one of the following: a hole injection layer, a hole transport layer, a hole assisting layer, a luminescence assisting layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. By means of the methods used in the art, at least two compounds can be included in the same layer or different layers. For example, they can be co-evaporated or co-deposited, or can be individually deposited.

[0029] The term "multiple host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which materials may be included in any light-emitting layer constituting an organic electroluminescent device. It may refer to both materials before being included in the organic electroluminescent device (e.g., before vapor deposition) and materials after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple host materials of the present disclosure may be a combination of two or more host materials and may optionally further include conventional materials included in the organic electroluminescent materials. Two or more compounds included in the multiple host materials of the present disclosure may be included in one light-emitting layer or may be separately included in different light-emitting layers. For example, two or more host materials may be co-evaporated or co-deposited, or individually deposited.

[0030] Herein, the term "(C1-C30)alkyl" means a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term "(C3-C30)cycloalkyl" or "(C3-C30)subcycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered)heterocycloalkyl" means a cycloalkyl having 3 to 7 ring backbone atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term "(C6-C30)aryl" or "(C6-C30)subaryl" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. The above aryl or subaryl may be partially saturated and may include a spiro structure. The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, Groups such as a base, a tetracenyl group, a fluoranthenyl group, a spirobifluorenyl group, a spiro[fluorene-benzofluorene] group, etc. The term “(3- to 30-membered) heteroaryl” or “(3- to 30-membered) heteroarylene” is an aryl or arylene group having 3 to 30 ring backbone atoms, wherein the number of ring backbone carbon atoms is preferably 5 to 30 and includes at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above-mentioned hetero(arylene) group may be monocyclic or a fused ring fused with at least one benzene ring; may be partially saturated; may be a hetero(arylene) group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may include a spiro structure. The above-mentioned heteroaryl group may include monocyclic heteroaryl groups such as a furyl group, a thienyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a thiadiazolyl group, an isothiazolyl group, an isoxazolyl group, an oxazolyl group, an oxadiazolyl group, a triazinyl group, a tetrazinyl group, a triazolyl group, a tetrazolyl group, a furazanyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, etc., and fused-ring heteroaryl groups such as a benzofuryl group, a benzothienyl group, an isobenzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a benzonaphthothiophenyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoisoxazolyl group, a benzoxazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a benzothiadiazolyl group, a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a quinazolinyl group, a quinoxalinyl group, a carbazolyl group, a benzocarbazolyl group, a phenoxazinyl group, a phenanthridinyl group, a benzodioxolyl group, etc. In addition, “halogen” includes F, Cl, Br, and I.

[0031] As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). In the present disclosure, the substituents of substituted alkyl, substituted alkylene, 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-aryl amino, or substituted alkylarylamino are each independently at least one selected from the group consisting of: tritium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl which is unsubstituted or substituted with one or more (C6-C30)aryl and / or one or more (3- to 30-membered)heteroaryl; (C6-C30)aryl which is unsubstituted or substituted with at least one of one or more (C1-C30)alkyl, one or more (C6-C30)aryl, and one or more (3- to 30-membered)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino which is unsubstituted or substituted with one or more (C1-C30)alkyl; (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 which is unsubstituted or substituted with one or more (C1-C10)alkyl and / or one or more (C6-C18)aryl; (3- to 25-membered)heteroaryl which is unsubstituted or substituted with one or more (C6-C18)aryl; di(C6-C18)arylamino; and (C1-C6)alkyl(C6-C25)aryl.For example, each substituent is independently at least one of the following: methyl, phenyl, naphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl substituted with one or more phenyl groups, benzo[c]carbazolyl substituted with one or more phenyl groups, benzonaphthothiophenylphenyl, and diphenylamino.

[0032] In the formulae of the present disclosure, a ring formed by the bonding of adjacent substituents means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic ring, or a combination thereof; preferably, a substituted or unsubstituted monocyclic or polycyclic (3-membered to 26-membered) alicyclic or aromatic ring, or a combination thereof; more preferably, an unsubstituted or alkyl-substituted monocyclic or polycyclic (5-membered to 10-membered) aromatic ring; and for example, a benzene ring, an indene ring substituted with one or more methyl groups, or a benzothiophene ring. In addition, the formed ring may 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.

[0033] Herein, a heteroaryl group, a heteroarylene group, and a heterocycloalkyl group 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, tritium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(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 tris(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.

[0034] In Formula 1, Ar1 to Ar3 each independently represent hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group. According to one embodiment of the present disclosure, Ar1 to Ar3 each independently represent a substituted or unsubstituted (C6-C29) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group. According to another embodiment of the present disclosure, Ar1 to Ar3 each independently represent a (C6-C29) aryl group that is unsubstituted or substituted with one or more (C1-C10) alkyl groups and / or one or more (C6-C18) aryl groups, or a (5- to 30-membered) heteroaryl group that is unsubstituted or substituted with one or more (C6-C18) aryl groups. Specifically, Ar1 may represent a dimethylfluorenyl group; a diphenylfluorenyl group; a dimethylbenzo[h]fluorenyl group; a diphenylbenzo[h]fluorenyl group; a carbazolyl group that is unsubstituted or substituted with one or more biphenyl groups; a benzocarbazolyl group that is unsubstituted or substituted with one or more phenyl groups and / or one or more biphenyl groups; a dibenzocarbazolyl group; or a (20- to 30-membered) heteroaryl group containing at least one of N, O, and S that is unsubstituted or substituted with one or more phenyl groups; and Ar2 and Ar3 may each independently represent a phenyl group; a naphthyl group; a biphenyl group; a terphenyl group; a phenanthryl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a dimethylbenzo[h]fluorenyl group; a diphenylbenzo[h]fluorenyl group; a spirobifluorenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group substituted with one or more phenyl groups; or a benzocarbazolyl group substituted with one or more phenyl groups.

[0035] L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group. According to one embodiment of the present disclosure, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (3-membered to 29-membered) heteroarylene group. According to another embodiment of the present disclosure, L1 to L3 each independently represent a single bond; an unsubstituted or substituted (C6-C18) arylene group by at least one of one or more (C1-C6) alkyl groups, one or more (C6-C18) aryl groups, and one or more bis(C6-C18) arylamino groups; or an unsubstituted nitrogen-containing (5-membered to 26-membered) heteroarylene group. Specifically, L1 to L3 may each independently represent a single bond, an unsubstituted or diphenylamino-substituted phenylene group, naphthylene group, phenylnaphthylene group, naphthylphenylene group, biphenylene group, dimethylfluorenyl group, or a nitrogen-containing (26-membered) heteroarylene group.

[0036] According to one embodiment of the present disclosure, Formula 1 may be represented by at least one of Formulas 1-1 to 1-14 below.

[0037]

[0038]

[0039]

[0040]

[0041] 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.

[0042] Y represents CR7R8, NR9, O, or S.

[0043] T1 to T 13 and X1 to X 12 each independently represent N or CV1; and preferably CV1.

[0044] Each V1 independently represents hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or two adjacent V1s may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, each V1 independently represents hydrogen, or a substituted or unsubstituted (C6-C25) aryl group: or two adjacent V1s may be connected or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3- to 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 V1 independently represents hydrogen or an unsubstituted (C6-C18) aryl group; or two adjacent V1s may be connected or fused to each other to form an unsubstituted monocyclic (3- to 10-membered) alicyclic or aromatic ring. For example, each V1 may independently represent hydrogen or a phenyl group; or two adjacent V1s may be connected or fused to each other to form a benzene ring.

[0045] L4 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group. According to one embodiment of the present disclosure, L4 represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. According to another embodiment of the present disclosure, L4 represents a single bond, or an unsubstituted (C6-C18) arylene group. For example, L4 may represent a single bond or a phenylene group.

[0046] P1 and P2 each independently represent a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group. P1 and P2 may be the same as or different from each other, and preferably they may be the same as each other. According to one embodiment of the present disclosure, P1 and P2 each independently represent a substituted or unsubstituted (C1-C20) alkyl group, or a substituted or unsubstituted (C6-C25) aryl group. According to another embodiment of the present disclosure, P1 and P2 each independently represent an unsubstituted (C1-C10) alkyl group, or an unsubstituted (C6-C18) aryl group. Specifically, P1 and P2 may each independently represent a methyl group or a phenyl group.

[0047] R2 to R9 and P3 to P5 each independently represent hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or those adjacent among R2 to R9 and P3 to P5 may be connected to each other to form one or more rings. R7 and R8 may be the same as or different from each other, and preferably they may be the same as each other. According to one embodiment of the present disclosure, R2 to R9 and P3 to P5 each independently represent hydrogen, a substituted or unsubstituted (C1-C20) alkyl group, or a substituted or unsubstituted (C6-C25) aryl group; or those adjacent among R2 to R9 and P3 to P5 may be connected or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3- to 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, R2 to R9 and P3 to P5 each independently represent hydrogen, an unsubstituted (C1-C10) alkyl group, or an unsubstituted (C6-C18) aryl group; or those adjacent among R2 to R9 and P3 to P5 may be connected or fused to each other to form an unsubstituted or alkyl-substituted monocyclic or polycyclic (5- to 10-membered) ring. For example, R2, R3, R6, and P3 may each independently represent hydrogen, or those adjacent among R2, R3, R6, and P3 may be connected to each other to form a benzene ring; R4 may represent hydrogen, or may be connected to one or more adjacent substituents to form a benzene ring, an indene ring substituted with one or more methyl groups, or a benzothiophene ring; R5, P4, and P5 may each independently represent hydrogen; R7 and R8 may represent methyl; and R9 may represent a phenyl group.

[0048] Ar4 represents hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group. According to one embodiment of the present disclosure, Ar4 represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, Ar4 represents an unsubstituted (C6-C18) aryl group. Specifically, Ar4 may represent a phenyl group or a biphenyl group.

[0049] Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, Ar5 and Ar6 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, Ar5 and Ar6 each independently represent an unsubstituted (C6-C18) aryl group. For example, Ar5 and Ar6 may each independently represent a phenyl group.

[0050] b, c, d, f, and g each independently represent an integer from 1 to 4; e represents an integer of 1 or 2; c″ and h each independently represent an integer from 1 to 3; and i represents an integer from 1 to 5; provided that if each of b to i and c″ is an integer of 2 or greater, each of R2 to R6 and P3 to P5 may be the same or different.

[0051] In Formula 2, X represents -N=, -NR 15 -, -O-, or -S-: Z represents -N=, -NR 16 -, -O-, or -S-; provided that when X represents -N=, Z represents -NR 16 -, -O-, or -S-, and when X represents -NR 15 -, Z represents -N=, -O-, or -S-. According to one embodiment of the present disclosure, X represents -N=, -NR 15 -, -O-, or -S-: and Z represents -N=, -NR 16 -, -O-, or -S-; provided that either X or Z represents -N=.

[0052] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (3- to 25-membered) heteroaryl. According to another embodiment of the present disclosure, HAr represents a (5- to 20-membered) heteroaryl substituted by one or more (C6-C30) aryls and / or one or more (3- to 25-membered) heteroaryls. Specifically, HAr may represent a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted triazinyl, or a 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 the following: phenyl, biphenyl, naphthyl, spirobifluorene, dimethylfluorene, diphenylfluorene, dimethylbenzofluorene, dibenzofuran, dibenzothiophene, benzonaphthothiophene, a carbazolyl substituted by one or more phenyls, and a benzocarbazolyl substituted by one or more phenyls.

[0053] In Formula 2, R 11 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, R 11 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 25-membered) heteroaryl. According to another embodiment of the present disclosure, R 11 represents an unsubstituted (C6-C29) aryl substituted by one or more (C1-C10) alkyls and / or one or more (C6-C18) aryls, or an unsubstituted (5- to 25-membered) heteroaryl substituted by one or more (C6-C18) aryls. Specifically, R 11 may represent phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorene, dimethylbenzofluorene, spirobifluorene, spiro[fluorene-benzofluorene], a carbazolyl substituted by one or more phenyls, a benzocarbazolyl substituted by one or more phenyls, dibenzofuran, or dibenzothiophene.

[0054] In Formula 2, R 12 to R 14each independently represents hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or, R 12 to R 14 among those adjacent to each other may be connected to each other to form one or more rings. For example, R 12 to R 14 may each independently represent hydrogen.

[0055] In Formula 2, R 15 and R 16 each independently represent hydrogen, tritium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group. According to one embodiment of the present disclosure, R 15 and R 16 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 15 and R 16 each independently represent an unsubstituted (C6-C18) aryl group. For example, R 15 may represent a phenyl group or a biphenyl group, and R 16 may represent a phenyl group.

[0056] In Formula 2, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. According to another embodiment of the present disclosure, L represents a single bond, or an unsubstituted (C6-C18) arylene group. Specifically, L may represent a single bond, a phenylene group, or a biphenylene group.

[0057] 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; wherein if b′, c′, and d′ are each independently an integer of 2 or greater, then R 12 to R 14 each may be the same or different.

[0058] According to one embodiment of the present disclosure, Formula 2 may be represented by at least one of the following Formulas 2-1 to 2-6.

[0059]

[0060] In Formulas 2-1 to 2-6, HAr, R 11 to R 16 , L, and a′ to d′ are as defined in Formula 2.

[0061] The compound represented by Formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The compound represented by Formula 2 may be specifically exemplified by the following compounds, but is not limited thereto.

[0072]

[0073]

[0074]

[0075]

[0076] A combination of at least one of Compounds C-1-1 to C-1-195 and at least one of Compounds C-2-1 to C-2-112 can be used in an organic electroluminescent device.

[0077] The compounds represented by Formula 1 and Formula 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. 10-2013-0106255 A (published on September 27, 2013), 10-2012-0042633 A (published on May 3, 2012), 10-2018-0099510 A (published on September 5, 2018), and 10-2015-0066202 A (published on June 16, 2015); the compound represented by Formula 2 can be prepared by referring to Korean Patent Application Publication No. 10-2017-0051198 A (published on May 11, 2017), but is not limited thereto.

[0078] [Reaction Scheme 1]

[0079]

[0080] [Reaction Scheme 2]

[0081]

[0082] [Reaction Scheme 3]

[0083]

[0084] In Reaction Schemes 1 to 3, T1 to T 13 , X1 to X 12 , L1 to L3, Ar2 and Ar3 are as defined in Formulae 1-4 and 1-7 above.

[0085] The 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 contain various organic electroluminescent materials, including a compound represented by Formula 1 as the first organic electroluminescent material and a compound represented by Formula 2 as the second organic electroluminescent material. According to an 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, and the light-emitting layer contains various host materials, the various host materials including a compound represented by Formula 1 as the first host material and a compound represented by Formula 2 as the second host material.

[0086] The light-emitting layer contains a host and a dopant. The host contains various host materials. The various host materials include a first host material and a second host material. The first host material may consist of a single compound represented by Formula 1 or at least one compound represented by Formula 1, and may further contain conventional materials included in the organic electroluminescent materials. The second host material may consist of a single compound represented by Formula 2 or at least one compound represented by Formula 2, and may further contain conventional materials included in the organic electroluminescent materials. 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 still more preferably about 50:50.

[0087] The light-emitting layer is a light-emitting layer and may be a single layer or a multi-layer in which two or more layers are stacked. Among the various host materials according to the present disclosure, the first host material and the second host material may both be included in one layer or may be separately included in different light-emitting layers. According to an embodiment of the present disclosure, the doping concentration of the dopant compound is less than about 20% by weight relative to the host compound in the light-emitting layer.

[0088] The organic electroluminescent device of the present disclosure may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting 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 an embodiment of the present disclosure, in addition to the various host materials of the present disclosure, the organic electroluminescent device may further include an amine-based compound as at least one of the following: a hole injection material, a hole transport material, a hole assisting material, a light-emitting material, a light-emitting assisting material, and an electron blocking material. Additionally, according to an embodiment of the present disclosure, in addition to the various host materials of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of the following: an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0089] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be selected from complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.

[0090] The dopant may include, but is not limited to, compounds represented by at least one of Formulas 101 to 103 below.

[0091]

[0092] In Formulas 101 to 103,

[0093] L is selected from the following Structure 1 and Structure 2:

[0094]

[0095] R 100 each independently represents hydrogen, tritium, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group;

[0096] R 101 to R 109 and R 111 to R 123 each independently represents hydrogen, tritium, a halogen, an unsubstituted or tritium- and / or one or more halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be connected to adjacent R 101 to R 109 and R 111 to R 123 to form one or more rings. Specifically, R 106 to R 109 may be connected to adjacent R 106 to R 109 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 to R 123 may be connected to adjacent R 120 to R 123 to form a ring, and for example, R 120 and R121 They can be connected to each other to form an unsubstituted benzene ring or a benzene ring substituted by at least one of one or more alkyl groups, one or more aryl groups, one or more arylalkyl groups, and one or more alkylaryl groups, an unsubstituted or alkyl-substituted fluorene ring, a dibenzofuran ring, or a dibenzothiophene ring;

[0097] R 124 to R 127 each independently represents hydrogen, tritium, a halogen, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or can be connected to adjacent R 124 to R 127 to form one or more rings, such as an unsubstituted or alkyl-substituted indene ring, an unsubstituted or alkyl-substituted benzothiophene ring, or an unsubstituted or alkyl-substituted benzofuran ring;

[0098] R 201 to R 211 each independently represents hydrogen, tritium, a halogen, an unsubstituted or tritium- and / or one or more halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or an unsubstituted or alkyl- and / or tritium-substituted (C6-C30) aryl group; or can be connected to adjacent R 201 to R 211 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;

[0099] r each independently represents an integer from 1 to 3, where if r is independently 2 or a larger integer, each of R 100 can be the same or different; and

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

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

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multiple layers in order to reduce 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 multiple layers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be multiple layers.

[0108] In addition, an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof, may be used between the light-emitting layer and the cathode. The electron buffer layer may be multiple layers in order to control the injection of electrons and improve the interfacial characteristics between the light-emitting layer and the electron injection layer, and each of the multiple layers may use two compounds simultaneously. The hole blocking layer or the electron transport layer may also be multiple layers, and each of the multiple layers may use multiple compounds.

[0109] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, and flow coating methods may be used.

[0110] When a solvent is used in the wet film-forming method, a thin film may be formed by dissolving or diffusing the material for forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material for forming each layer can be dissolved or diffused, and there is no problem in terms of film-forming ability.

[0111] In addition, the first host compound and the second host compound may be formed into a film by a co-evaporation method or a mixture evaporation method in the methods listed above. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding single crucible sources and current is applied to two chambers simultaneously to evaporate the materials. Mixture evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chamber to evaporate the materials. In addition, when the first host compound and the second host compound are present in the same layer or different layers of the organic electroluminescent device, the two host compounds may be deposited individually. For example, the first host compound may be deposited, and then the second host compound may be deposited.

[0112] The present disclosure can provide a display system by using a plurality of host materials, the plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display system or an illumination system can be produced by using the plurality of host materials of the present disclosure. Specifically, a display system, such as a display system for a smartphone, a tablet computer, a laptop computer, a PC, a TV, or an automobile; or an illumination system, such as an outdoor or indoor illumination system, can be produced by using the plurality of host materials of the present disclosure.

[0113] Hereinafter, the preparation method and physical properties of the compound according to the present disclosure and the characteristics of the OLED according to the present disclosure will be explained in detail. However, the following examples only illustrate in detail the preparation method of the compound according to the present disclosure and the characteristics of the OLED, but the present disclosure is not limited to the following examples.

[0114] Example 1: Synthesis of Compound C-2-95

[0115]

[0116] 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 (Pd(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 one day. After the reaction was completed, the reaction mixture was cooled to room temperature and then filtered through diatomaceous earth with dichloromethane (MC). The filtrate was distilled under reduced pressure and then separated by column chromatography with dichloromethane / hexane (MC / Hex) to obtain 2.7 g of Compound C-2-95 (yield: 57%).

[0117] Compound MW Melting Point C-2-95 499.6 266℃

[0118] Example 2: Synthesis of Compound C-2-112

[0119]

[0120] 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 h. After the reaction was completed, 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%).

[0121] Compound MW Melting Point C-2-112 576.6 231℃

[0122] Example 3: Synthesis of Compound C-2-105

[0123]

[0124] 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 h. After the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added thereto. The resulting solid was filtered under reduced pressure and then separated by column chromatography with MC to obtain 4.6 g of compound C-2-105 (yield: 80%).

[0125] Compound MW Melting Point C-2-105 602.7 227℃

[0126] Example 4: Synthesis of Compound C-2-93

[0127]

[0128] 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 the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added thereto. The resulting solid was filtered under reduced pressure and then separated by column chromatography with MC to obtain 3.3 g of compound C-2-93 (yield: 75%).

[0129] Compound MW Melting Point C-2-93 616.7 282℃

[0130] Example 5: Synthesis of Compound C-2-94

[0131]

[0132] 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 7 mL of purified water, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added thereto. The resulting solid was filtered under reduced pressure and then separated by column chromatography with MC to obtain 3.45 g of compound C-2-94 (yield: 63%).

[0133] Compound MW Melting Point C-2-94 576.6 268℃

[0134] Example 6: Synthesis of Compound C-1-138

[0135]

[0136] 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 s-phos (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 the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added thereto. The resulting solid was filtered under reduced pressure and then separated by column chromatography with MC / Hex to obtain 2.3 g of compound C-1-138 (yield: 34%).

[0137] Compound MW Melting Point C-1-138 610.8 132℃

[0138] Example 7: Synthesis of Compound C-1-159

[0139]

[0140] 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 s-phos (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 the reaction was completed, the reaction mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added thereto. The resulting solid was filtered under reduced pressure and then separated by column chromatography with MC / Hex to obtain 4.0 g of compound C-1-159 (yield: 46%).

[0141] Compound MW Melting Point C-1-159 573.7 317℃

[0142] Example 8: Synthesis of Compound C-1-141

[0143]

[0144] 1) Synthesis of Compound E

[0145] 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 K3PO4 (68.6 mmol) were added to 170 mL of toluene, and the mixture was stirred at 145 °C under reflux for 3 hours. After the reaction was completed, the reaction mixture was extracted with MC and then dried over MgSO4. The residue was separated by column chromatography and then MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 9.0 g of compound E (yield: 59%).

[0146] 2) Synthesis of Compound C-1-141

[0147] 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 s-phos (1 mmol), and 2.691 g of NaOt-Bu (28 mmol) were added to 60 mL of toluene, and the mixture was stirred at 100 °C under reflux for 0.5 hour. After the reaction was completed, the reaction mixture was extracted with MC and then dried over MgSO4. The residue was separated by column chromatography and then MeOH was added thereto. The resulting solid was filtered under reduced pressure to obtain 1.3 g of compound C-1-141 (yield: 19%).

[0148] Compound MW Color Melting Point C-1-141 610.76 Yellow 168℃

[0149] Example 9: Synthesis of Compound C-1-195

[0150]

[0151] 1) Synthesis of Compound F

[0152] 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 K3PO4 (129 mmol) were added to 250 mL of toluene, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then filtered through silica gel. The organic layer was concentrated and then recrystallized from EA to obtain 14.2 g of compound F (yield: 62%).

[0153] 2) Synthesis of Compound C-1-195

[0154] 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 with MC / Hex to obtain 14.6 g of compound C-1-195 (yield: 76%).

[0155] Compound MW Melting Point C-1-195 610.7 141℃

[0156] Device Examples 1-1 to 7: Production of OLEDs According to the Present Disclosure

[0157] The OLED according to the present disclosure is produced as follows: The indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on the glass substrate of the OLED was subjected to ultrasonic washing successively with trichloroethylene, acetone, ethanol and distilled water and then stored in isopropyl alcohol. The ITO substrate was mounted on the substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6Then, an electric current is applied to the chamber to evaporate the material introduced above, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: The first host compound and the second host compound shown in Table 1 are introduced into two chambers of the vacuum vapor deposition apparatus as hosts respectively, and compound D-71 is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, and at the same time, the dopant material is evaporated at a different rate, so as to be deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant, thereby forming a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 are evaporated at a rate of 1:1 in two other chambers to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED is produced.

[0158]

[0159] Comparative Examples 1 to 7: Production of OLEDs Not According to the Present Disclosure

[0160] An OLED is produced in the same manner as in Device Example 1-1, except that only the second host compound shown in Table 1 is used instead of the two hosts.

[0161] The luminous efficiency of the OLEDs produced in the device examples and the comparative examples at a brightness of 5,000 nits, and the time (T96) required to reduce from 100% initial brightness to 96% brightness under a constant current at a brightness of 5,000 nits are shown in Table 1 below.

[0162] [Table 1]

[0163]

[0164] Device Examples 8 to 15: Production of OLEDs According to the Present Disclosure

[0165] In addition to using the first host compound and the second host compound shown in Table 2, an OLED was produced in the same manner as in Device Example 1-1. The luminous efficiency of the OLED produced in the device example at a brightness of 1,000 nits, and the time (T95) required to decrease from 100% initial brightness to 95% brightness under a constant current at a brightness of 5,000 nits are shown in Table 2 below.

[0166] [Table 2]

[0167]

[0168] 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 article. From the above device examples and comparative examples, it was confirmed that the organic electroluminescent device according to the present disclosure has a luminous efficiency that is at least 17.5% higher and an improved lifespan of at least 100 hours compared to conventional organic electroluminescent devices.

Claims

1. A plurality of host materials, the plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by Formula 1-4, 1-8, 1-9, 1-10 or 1-11: Wherein, Ar2 and Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30) alkylsilyl, substituted or unsubstituted bis(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tris(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, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-membered to 30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene; Ar5 represents substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl; T1 to T 13 and X1 to X 12 each independently represents N or CV1; V1 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, or deuterium-substituted or unsubstituted (C6-C30) aryl; or two adjacent V1s may be connected to each other to form one or more rings; Provided that, except for the case where all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen; and The second host material comprises a compound represented by Formula 2: Wherein, X represents -N=, -NR 15 -, -O-, or -S-; Z represents -N=, -NR 16 -, -O- or -S-; provided that when X represents -N=, Z represents -NR 16 -, -O- or -S-, and when X represents -NR 15 -, Z represents -N=, -O- or -S-; HAr represents substituted or unsubstituted (3-membered to 30-membered) heteroaryl; R 11 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 12 to R 14 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or R 12 to R 14 adjacent ones of which may be joined to each other to form one or more rings; R 15 and R 16 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; L represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-membered 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 from 1 to 4; wherein if b', c' and d' are each independently an integer of 2 or greater, then R 12 to R 14 each of them can be the same or different.

2. The multiple main materials according to claim 1, wherein Ar1 to Ar3, L1 to L3, HAr, R 11 to R 16 and the substituents of the substituted alkyl, substituted alkylene, 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 in L are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or substituted by one or more (C6-C30)aryl (3- to 30-membered)heteroaryl; unsubstituted or substituted by one or more (3- to 30-membered)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; amino; mono- or di-(C1-C30)alkylamino; unsubstituted or substituted by one or more (C1-C30)alkyl mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)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 multiple main materials according to claim 1, wherein, Formula 2 is represented by at least one of Formulas 2-1 to 2-6: Wherein, HAr, R 11 to R 16 L and a' to d' are as defined in claim 1.

4. The multiple main materials according to claim 1, wherein, HAr represents substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted triazinyl, or substituted or unsubstituted pyrimidinyl.

5. The plurality of main body materials according to claim 1, wherein, The compound represented by Formula 1 is at least one selected from the group consisting of the following compounds:

6. The multiple main materials according to claim 1, wherein The compound represented by Formula 2 is at least one selected from the group consisting of the following compounds:

7. An organic electroluminescent device, which includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein, At least one layer in the light-emitting layer comprises the plurality of host materials according to Claim 1.

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