KR20190109261A - Composition material for organic electroluminescent device, plurality of host materials, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a composite material for an organic electroluminescent device, to a plurality of host materials, and to an organic electroluminescent device comprising the same, wherein the organic electroluminescent device having high luminous efficiency and/or long service life is produced by comprising the composite material for the organic electroluminescent device including a specific combination of a compound.

Description

COMPOSITION MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, PLURALITY OF HOST MATERIALS, AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to a composite material for an organic electroluminescent device, a plurality of host materials and an organic electroluminescent device comprising the same.

Since Eastman Kodak's Tang et al. Developed the first TPD / Alq3 double-layer low molecular green organic electroluminescent device (OLED) consisting of a light emitting layer and a charge transfer layer in 1987, research on organic electroluminescent devices is rapidly and rapidly commercialized. Reached. Currently, organic electroluminescent devices mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. There is a need for OLEDs having high luminous efficiency and / or long life for long time use and high resolution of displays.

US Patent No. 6,902,831 discloses an azulene derivative as an organic electroluminescent compound, and Korean Patent Publication Nos. 2016-0022784 and 2017-0001563 disclose a plurality of compounds having carbazole derivatives and carbazole-carbazole structures. Although an organic electroluminescent device including a species of host compound is disclosed, development for improving the performance of the OLED device is still required.

U.S. Patent Publication No. 6,902,831 issued 2005.6.7. Korean Patent Publication No. 2016-0022784 (Published on March 2, 2016) Korean Patent Publication No. 2017-0001563 (published Jan. 2017)

An object of the present application is to provide an organic electroluminescent device having characteristics of high luminous efficiency and / or long life by including a composite material for an organic electroluminescent device containing a specific combination of compounds.

The present inventors have found that the composite material for an organic electroluminescent device comprising the compound represented by the following Chemical Formula 1 and the compound represented by the following Chemical Formula 2 achieves the above-mentioned object, and completed the present invention.

[Formula 1]

In Chemical Formula 1,

M is NL- (Ar) _a , S or O,

L is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene,

Ar is 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 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,

Y ₁ to Y ₁₂ are each independently N or CR ₁ ,

R ₁ is 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; Adjacent R _{1 's may} be fused to each other to form a substituted or unsubstituted ring,

a is an integer from 1 to 4, and when a is an integer of 2 or more, each Ar may be the same or different;

[Formula 2]

In Chemical Formula 2,

A ₁ is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl,

L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene,

X ₁ to X ₈ Are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl , -NR ₅ R ₆ or -SiR ₇ R ₈ R _9, or adjacent substituents may be fused to each other to form a ring, provided that any one of X ₁ to X ₈ is substituted or unsubstituted carbazolyl Except

R ₅ to R ₉ are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl , Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3 -30 membered) heteroaryl, or adjacent substituents may be fused to each other to form a ring.

By including the composite material for an organic electroluminescent device according to the present application, an organic electroluminescent device having high light emitting efficiency and / or long life characteristics can be manufactured.

The present application is described in more detail below, but for the purpose of description and should not be construed to limit the scope of the present application.

As used herein, "composite material for organic electroluminescent device" means that two or more materials that can be used in the organic electroluminescent device are present or prepared to be present together. Here, "existing together" does not mean only a state in which two or more materials are mixed, but also includes states that are separated from each other. In addition, the composite material for an organic EL device encompasses not only a material before being included in the organic EL device (eg, before deposition) but also a material included in the organic EL device (eg, after deposition). Concept. For example, the composite material for an organic EL device may include a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (host material and a dopant material), an electron buffer material, a hole blocking material. Two or more of a material, an electron transport material, and an electron injection material. Or two or more hole injection materials, two or more hole transport materials, two or more hole auxiliary materials, two or more light emitting auxiliary materials, two or more electron blocking materials, two or more light emitting materials (host materials and dopant materials) , Two or more electron buffer materials, two or more hole blocking materials, two or more electron transfer materials, or two or more electron injection materials. The composite material for an organic EL device of the present application may be included in any layer constituting the organic EL device, and two or more materials included in the composite material may be included together in one layer, and may be included in each other layer. It may be. When two or more kinds of materials are included in one layer, they may be mixed and deposited to form a layer, or may be separately co-deposited to form a layer.

As used herein, "plural species of host material" means a host material comprising a combination of two or more compounds that can be included in any light emitting layer constituting the organic electroluminescent device, and is not included in the organic electroluminescent device (e.g., For example, it may mean both before and after the deposition (eg, after deposition). In one example, the plurality of host materials of the present application is a combination of two or more host materials, optionally, may further include a conventional material included in the organic electroluminescent material. Two or more compounds included in the plural kinds of host materials of the present application may be included together in one light emitting layer through a method used in the art, or may be included in different light emitting layers, respectively. For example, the two or more compounds may be mixed or co-deposited or deposited separately.

As used herein, "(C1-C30) alkyl" means a straight or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein it is preferably 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms. More preferred. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert -butyl. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S And cycloalkyl comprising at least one heteroatom selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30) aryl (ene)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, which may be partially saturated, wherein the ring backbone carbon number is It is preferable that it is 6-20, and it is more preferable that it is 6-15. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzoflu Orenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, peryllenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azule And a nil group. More specifically, examples of the aryl include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, benzanthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, naphthacenyl group, pyrenyl group, 1-crisenyl group, 2-crissenyl group, 3-crissenyl group, 4 -Crissenyl group, 5-Crissenyl group, 6-Crissenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-tri Phenylenyl group, 4-triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, benzofluorenyl group, dibenzofluore Nyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-terphenyl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2- Diary, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-quaterphenyl group, 3-fluoranthenyl group, 4-fluoranthenyl group, 8- Laurantenyl group, 9-fluoranthenyl group, benzofluoranthenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5 -Xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 4'-methylbiphenylyl group, 4 "-t- Butyl-p-terphenyl-4-yl group, 9,9-dimethyl-1-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-dimethyl-3-fluorenyl group, 9,9 -Dimethyl-4-fluorenyl group, 9,9-diphenyl-1-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-3-fluorenyl group, 9, 9-diphenyl-4-fluorenyl group, etc. In this application, "(3-50 membered) heteroaryl (ene)" has 3-50 ring skeleton atoms, and B, N, O, S, Si is mentioned. And an aryl group including one or more heteroatoms selected from the group consisting of P. Here, it is preferable that the number of ring skeleton atoms is 3 to 30, more preferably 5 to 20. The number heteroatom preferably may be from 1 to four, gyeil a single ring system or one or more fused benzene ring and condensed ring, and may be partially saturated. In addition, the heteroaryl (ene) herein also includes a form in which one or more heteroaryl or an aryl group is connected to a heteroaryl group by a single bond. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzonaphthothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindoleyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl And fused ring heteroaryl such as isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, and benzodioxolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5- Pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1 -Imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7 -Indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group , 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group , 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 6-isoindolyl Group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7 -Benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-qui Tealyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoqui Tealyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacar Zolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenantridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthtridi Neyl group, 6-phenantridinyl group, 7-phenantridinyl group, 8-phenantridinyl group, 9-phenantridinyl group, 10-phenantridinyl group, 1-acridinyl group, 2-acridinyl group, 3 -Acridinyl group, 4-acridinyl group, 9-acridinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3 -Furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group , 3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butylpyrrole-4-yl group, 3- (2-phenylpropyl) pyrrole-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2- t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t- Butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzo Thiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-silafluorenyl group, 2-silafluorenyl group, 3-silafluorenyl group, 4-silafluore And a germane group, a 1-germafluorenyl group, a 2-germafluorenyl group, a 3-germafluorenyl group, and a 4-germafluorenyl group. "Halogen" herein includes F, Cl, Br and I atoms.

In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other, for example, when the substituent is in the 1, 2 position in the benzene substituent, it is called an ortho position. Meta indicates that the two substituents are in positions 1 and 3, and for example, the meta position is referred to when the substituents are in positions 1 and 3 in the benzene substituent. Para indicates that two substituents are located at 1,4 positions, and for example, para is called a para position when a substituent is located at 1, 4 positions in a benzene substituent.

In addition, in the description of "substituted or unsubstituted" as described herein, "substituted" means that the hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. Substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted in Ar, L, R ₁ to R ₉ , R ₁₆ , A ₁ , L _{1 ,} X ₁ to X ₈ in the formulas herein Heterocycloalkyl, substituted aryl (ene), substituted heteroaryl (ene), substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono- Or the substituents of di-alkylamino, substituted mono- or di-arylamino, and substituted alkylarylamino are each independently deuterium; halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C 1 -C 30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-50 membered) heteroaryl unsubstituted or substituted with (C1-C30) alkyl, (C6-C30) aryl and / or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3- to 50-membered) heteroaryl and / or tri (C6-C30) arylsilyl; 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; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) ar (C1-C30) alkyl; And (C1-C30) alkyl (C6-C30) aryl. The substituent is preferably (C1-C20) alkyl; (C6-C25) aryl unsubstituted or substituted with (C1-C20) alkyl and / or (3- to 30-membered) heteroaryl; (3-40 membered) heteroaryl unsubstituted or substituted with (C1-C20) alkyl and / or (C6-C25) aryl; And di (C6-C20) arylamino. For example, the substituent may be methyl; tert -butyl; Phenyl unsubstituted or substituted with pyridinyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl and / or dibenzothiophenyl; Naphthyl unsubstituted or substituted with diphenyltriazinyl; Biphenyl; Naphthylphenyl; Terphenyl; Dimethyl fluorenyl; Phenylfluorenyl; Diphenylfluorenyl; Phenanthrenyl; Triphenylenyl; Pyridinyl; Triazinyl substituted with one or more of phenyl and naphthyl; Indolyl substituted with diphenyl; Benzoimidazolyl substituted with phenyl; Quinolyl; Quinazolinyl substituted with phenyl and / or biphenyl; Quinoxalinyl substituted with phenyl; Carbazolyl unsubstituted or substituted with phenyl; Dibenzofuranyl; Dibenzothiophenyl; Benzocarbazolyl unsubstituted or substituted with phenyl; Dibenzocarbazolyl; Benzophenanthrothiophenyl; Diphenylamino; Dimethylfluorenylphenylamino; Or substituted or unsubstituted (16-33 membered) heteroaryl containing one or more of nitrogen, oxygen, and sulfur.

In the general formula of the present application, when adjacent substituents are linked to or fused to each other to form a substituted or unsubstituted (3- to 30-membered) ring, the ring may be a ring of monocyclic or polycyclic alicyclic, aromatic, or a combination thereof. have. The ring may also comprise one or more heteroatoms selected from nitrogen, oxygen and sulfur. For example, the ring may be substituted or unsubstituted dibenzothiophene ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted flu Orene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted indole ring, substituted or unsubstituted indene ring, substituted or unsubstituted benzene ring, or substituted or unsubstituted Ring carbazole ring and the like.

In the formulas herein, heteroaryls (enes) may each independently include one or more heteroatoms selected from B, N, O, S, Si, and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1) -C30) 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) aryl One or more selected from the group consisting of amino may be bonded.

In Formula 1, M is NL- (Ar) _a , S or O.

In Formula 1, L is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Preferably single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (5- to 25-membered) heteroarylene; More preferably, it may be a single bond, unsubstituted (C6-C18) arylene, or unsubstituted (5- to 18-membered) heteroarylene, wherein the heteroarylene may contain at least one of nitrogen, oxygen, and sulfur. Can be. According to an aspect of the present invention, in formula 1, L is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted Or unsubstituted pyrimidylene, substituted or unsubstituted triazinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted naphthyridinylene, substituted or unsubstituted benzo (13-16 membered) hetero-containing one or more of quinazolinylene, substituted or unsubstituted benzothienopyrimidinylene, substituted or unsubstituted acenaphtopyrimidinylene, substituted or unsubstituted nitrogen, oxygen and sulfur Arylene and the like.

In Formula 1, Ar is 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 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; Preferably Substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, or substituted or unsubstituted di (C6-C25) arylamino; More preferably substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5- to 25-membered) heteroaryl, Or substituted or unsubstituted di (C6-C18) arylamino.

According to an aspect of the present invention, in formula 1 Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triazineyl, Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted Benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted Or unsubstituted pyrazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted Benzofuran Substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted benzothienoquinolinyl, substituted or unsubstituted benzofuroquinolinyl, substituted or unsubstituted tria Indenyl, substituted or unsubstituted phenanthromidazolyl, substituted or unsubstituted (9-25 membered) heteroaryl containing one or more of nitrogen, oxygen and sulfur, substituted or unsubstituted diphenylamino, substituted or unsubstituted Phenylbiphenylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted fluorenylphenylamino, or substituted or unsubstituted fluorenylbiphenylamino.

In Formula 1, a is an integer of 1 to 4, preferably 1 or 2. When a is an integer of 2 or more, each Ar may be the same or different.

In Formula 1, Y ₁ to Y ₁₂ are each independently N or CR ₁ . According to an aspect of the present invention, Y ₁ to Y ₁₂ May all be CR ₁ , and according to another aspect of the present disclosure, at least one of Y ₁ to Y ₁₂ may be N.

Herein, R ₁ is 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) aryl Amino; Adjacent R ₁ may be fused to each other to form a substituted or unsubstituted ring. R ₁ is preferably hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5- to 25-membered) heteroaryl, or substituted or unsubstituted Ring di (C6-C25) arylamino; May be linked to an adjacent substituent to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic aromatic ring, wherein at least one carbon atom of the aromatic ring formed is selected from nitrogen, oxygen and sulfur May be replaced by one or more heteroatoms; More preferably hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5- to 18-membered) heteroaryl, or substituted or unsubstituted Di (C6-C18) arylamino; May be linked to an adjacent substituent to form a substituted or unsubstituted (C5-C18) monocyclic or polycyclic aromatic ring, wherein at least one carbon atom of the aromatic ring formed is selected from nitrogen, oxygen and sulfur It may be replaced with one or more heteroatoms. According to one aspect of the invention, R ₁ is hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl , Substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazineyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phenylbiphenylamino, and the like.

According to an aspect of the present invention, in Formula 1, at least an adjacent pair of Y ₁ to Y ₁₂ is CR ₁ , and R ₁ of the two adjacent CR ₁ are fused to each other to be independently of Formulas 1-11 to 1-15 It may form a ring represented by any one of, but is not limited thereto. Here, Y ₁ and Y ₂ , Y ₅ and Y ₆ , and Y ₉ and Y ₁₀ are also considered to be adjacent to each other. For example, the ring formed may include a ring of the formula 1-11 to 1-15 substituted or unsubstituted benzene ring, naphthalene ring, furan ring, thiophene ring, substituted or unsubstituted pyrrole ring, pyridine ring, Benzofuran ring, benzothiophene ring, substituted or unsubstituted indole ring, dibenzofuran ring, dibenzothiophene ring, substituted or unsubstituted carbazole ring, or phenanthrene ring.

[Formula 1-11] [Formula 1-12] [Formula 1-13] [Formula 1-14] [Formula 1-15]

는 상기 화학식 1의 인접한 CR₁에서의 C와 R₁의 융합 부위를 나타낸다. In Chemical Formulas 1-11 to 1-15,

Represents a fused portion of the C and R ₁ of the adjacent CR ₁ in the general formula (1).

In Formulas 1-13 and 1-15, X is N or CR ₄ . According to an aspect of the present disclosure, X may be all CR ₄ , and according to another aspect of the present disclosure, at least one of X may be N. R ₄ is 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, preferably Preferably substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted Ringtone (5-18 won) A reel.

In Formula 1-14, R ₃ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 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; Preferably substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; More preferably unsubstituted (C6-C18) aryl, or unsubstituted (5- to 18-membered) heteroaryl; For example, it may be phenyl.

The compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1] [Formula 1-2]

In Formulas 1-1 and 1-2, M and Y ₂ to Y ₁₂ are the same as defined in Formula 1, and Y ₁₃ and Y ₁₄ are each independently the same as the definition of Y ₂ .

In Formula 1-1, Y ₁ is N or CR ₂ , R ₂ is 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.

In Formula 2, A ₁ is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably unsubstituted (C6-C25) aryl, or (5- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, more preferably unsubstituted or unsubstituted with (C6-C18) aryl, or (C6-C18) aryl ( 5-18 membered) heteroaryl. For example, A ₁ is phenyl; Naphthyl; Biphenyl; Terphenyl; Triazinyl substituted with one or more of phenyl, naphthyl and biphenyl; Diphenylpyridinyl; Phenylquinoline; Phenylquinoxaline; Phenylquinazolinyl; Biphenylquinazolinyl; Quinazolinyl substituted with phenylcarbazole; Dibenzofuranyl; Dibenzothiophenyl; Or phenylcarbazolyl.

In Formula 2, L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene, preferably a single bond, unsubstituted (C6-C25) arylene or unsubstituted (5- to 25-membered) heteroarylene, more preferably single bond, unsubstituted (C6-C18) arylene, or unsubstituted (5- to 18-membered) Heteroarylene. For example, L ₁ may be a single bond, phenylene, naphthylene, biphenylene, quinolinylene, quinoxalinylene, quinazolinylene, or carbazolylene.

In Formula 2, X ₁ to X ₈ Are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl , -NR ₅ R ₆ or -SiR ₇ R ₈ R _9, or adjacent substituents may be fused to each other to form a ring; Preferably hydrogen, unsubstituted (C6-C25) aryl, or unsubstituted (5- to 25-membered) heteroaryl, or adjacent substituents may be fused to each other to form a ring; More preferably hydrogen, unsubstituted (C6-C18) aryl, or unsubstituted (5- to 18-membered) heteroaryl, or adjacent substituents may be fused to each other to form a ring. Provided that any one of X ₁ to X ₈ is substituted or unsubstituted carbazolyl. For example, X ₁ to X ₈ Are each independently hydrogen, phenyl, dibenzofuranyl, or dibenzothiophenyl, or adjacent substituents are fused to each other to form a benzene ring, a substituted indole ring, a benzothiophene ring, a benzofuran ring, a substituted benzoindole ring, a naph It may form a tofuran ring, naphthothiophene ring, or azepine ring. Substituents of the substituted indole ring are phenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl and / or phenyl unsubstituted or substituted with dibenzothiophenyl, unsubstituted Naphthylphenyl, unsubstituted biphenyl, unsubstituted terphenyl, phenyl substituted quinoxalinyl, phenyl substituted quinazolinyl, and diphenyltriazinyl substituted naphthyl. The substituent of the substituted benzoindole ring may be one or more of phenyl, naphthylphenyl, biphenyl, and dibenzofuranyl unsubstituted or substituted with benzofuranyl or dibenzothiophenyl.

In Formula 2, R ₅ to R ₉ are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3 -C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or Unsubstituted (3- to 30-membered) heteroaryl, or adjacent substituents may be fused to each other to form a ring.

The compound represented by Chemical Formula 2 may be represented by any one of the following Chemical Formulas 2-1 to 2-8.

[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-5] [Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Formulas 2-1 to 2-8, A ₁ , L _{1 ,} X ₁ to X ₄ are the same as defined in Formula 2, X ₉ to X ₃₈ are each independently the same as defined in X ₁ , b, e, f, g, h and l are each independently 1 or 2, c, d and i are each independently an integer of 1 to 3, j and k are each independently an integer of 1 to 4, b to When l is an integer of 2 or more, each of X ₉ , X ₁₄ , X ₁₉ , X ₂₀ , X ₂₁ , X ₃₀ , X ₃₁ , and X ₃₅ to X ₃₈ may be the same or different from each other. In Formula 2-2, Z is O or S.

In Formulas 2-1 and 2-4 to 2-6, V and W are each a single bond, NR _{16 ,} O or S, provided that both V and W are not a single bond, or both NR ₁₆ . According to one aspect of the present disclosure, either V and W are single bonds, and the other may be NR _{16 ,} O or S.

R ₁₆ is hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl Is; Preferably (C6-C25) aryl unsubstituted or substituted with (3- to 30-membered) heteroaryl, or (5- to 25-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl; More preferably, they are (C6-C18) aryl unsubstituted or substituted with (5- to 25-membered) heteroaryl, or (5- to 18-membered) heteroaryl substituted with (C6-C18) aryl. For example, R ₁₆ is phenyl unsubstituted or substituted with diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzothiophenyl and / or dibenzofuranyl; Naphthyl substituted with diphenyltriazinyl; Biphenyl; Terphenyl; Naphthylphenyl; Quinazolinyl substituted with phenyl; Or quinoxalinyl substituted with phenyl.

In Formulas 2-1 to 2-8, X ₁ to X ₄ , and X ₉ to X ₃₈ are each independently preferably hydrogen or unsubstituted (C6-C25) aryl, or adjacent substituents are fused to each other. May form a ring; More preferably hydrogen or unsubstituted (C6-C18) aryl, or adjacent substituents may be fused to each other to form a ring. For example, X ₁ to X ₄ , and X ₉ to X ₃₀ may each independently be hydrogen or phenyl, X ₃₁ to X ₃₈ may be hydrogen, and X ₁ and X ₂ , X ₃ and X ₄ , And two adjacent X _{21 's} may each be fused to each other to form an indole ring substituted with phenyl, or an unsubstituted benzene ring.

The compound represented by Formula 1 may be one or more selected from the following compounds, but is not limited thereto.

The compound represented by Formula 2 may be one or more selected from the following compounds, but is not limited thereto.

The compound represented by the formula (1) according to the present application can be prepared by synthetic methods known to those skilled in the art. For example, the compound of Formula 1 may be prepared by referring to the following method.

Scheme 1

Scheme 2

Scheme 3

Scheme 4

Scheme 5

Scheme 6

In Schemes 1 to 6, L, Ar, Y ₁ to Y ₁₂ , and a are the same as defined in the formula (1).

Compound represented by the formula (2) of the present application can be prepared by a synthetic method known to those skilled in the art, for example, Korean Patent Publication No. 2015-0135109 (Dec. 2, 2015), 2015-0032447 (2015.03. 26. Publication), 2016-0099471 (published on August 22, 2016), and 2018-0012709 (published on February 6, 2018), but is not limited thereto.

Meanwhile, the composite material for an organic electroluminescent device of the present application may be a plurality of types of host materials, the compound represented by Formula 1 may be a first host material, and the compound represented by Formula 2 may be a second host material. The composite material for an organic electroluminescent device of the present application may be made of only the first host material represented by Chemical Formula 1 and the second host material represented by Chemical Formula 2, and may further include conventional materials included in the host material. have. The composite material for an organic electroluminescent device of the present application has a ratio of the compound represented by Formula 1 and the compound represented by Formula 2 in a ratio of about 1:99 to about 99: 1, preferably about 10:90 to about 90:10. Ratio, more preferably about 30:70 to about 70:30. In addition, the compound represented by the formula (1) and the compound represented by the formula (2) in a desired ratio, the method of mixing in the shaker and mixing, the method of putting in a glass tube after dissolving by heating, or collecting in a solvent or the like Can be combined. Also provided herein is an organic electroluminescent material comprising a plurality of host materials of the present disclosure, in accordance with one aspect.

In addition, the present application can provide an organic electroluminescent device comprising a compound represented by Formula 1 and a compound represented by Formula 2. Specifically, the organic electroluminescent device of the present application includes at least one light emitting layer between an anode and a cathode, the light emitting layer includes a host and a dopant, and the host may include a composite material for the organic electroluminescent device of the present application. Can be. The organic electroluminescent device of the present application may include a compound represented by Formula 1 as a first host material and a compound represented by Formula 2 as a second host material.

The light emitting layer may be a single layer as a light emitting layer, and may be a plurality of layers in which two or more layers are stacked. According to one aspect of the present application, the doping concentration of the dopant compound with respect to the host compound of the light emitting layer may be less than 20% by weight.

The organic electroluminescent device of the present application is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, a hole blocking layer and an electron blocking layer It may further comprise one or more layers.

As the dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants may be used, and a phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) , In some cases, preferably, ortho-metalized complex compounds of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and more preferably in some cases, Ortho-metalized iridium complex compounds.

As a dopant included in the organic electroluminescent device of the present application, a compound represented by the following Formula 101 may be used, but is not limited thereto.

[Formula 101]

In Chemical Formula 101,

L is selected from the following structures 1 to 3;

[Structure 1] [Structure 2] [Structure 3]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium or (C1-C30) alkyl substituted or unsubstituted, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted ( C6-C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₀ to R ₁₀₃ are substituted or unsubstituted fused rings in which adjacent substituents are linked to each other, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted Or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline formation is possible;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium or (C1-C30) alkyl substituted or unsubstituted, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted ( C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₄ to R ₁₀₇ are fused with substituted or unsubstituted fused rings, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted with adjacent substituents connected to each other; Unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine is possible;

R ₂₀₁ to R ₂₂₀ are each independently hydrogen, deuterium, halogen, deuterium or (C1-C30) alkyl substituted or unsubstituted, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl and R ₂₀₁ to R ₂₂₀ may be linked to each other to form a substituted or unsubstituted fused ring with adjacent substituents;

n is an integer of 1-3.

Specifically, specific examples of the dopant compound are as follows, but are not limited thereto.

The organic electroluminescent device according to the present application comprises a first electrode; Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic layer includes a light emitting layer and is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer and an electron blocking layer. It may further comprise one or more layers. Each of these layers may be further composed of several layers.

The first electrode and the second electrode may be each formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a double side emission type according to the type of material forming the first electrode and the second electrode. Also, the hole injection layer may be further doped with P-dopant, and the electron injection layer may be further doped with n-dopant.

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

In addition, in the organic electroluminescent device of the present application, the organic material layer is at least one metal selected from the group consisting of Group 1, Group 2, 4 cycle transition metal, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element, Or may further comprise one or more complex compounds comprising such metals.

In addition, the organic electroluminescent device of the present application may emit white light by further including one or more light emitting layers including blue, red or green light emitting compounds known in the art in addition to the compound of the present application. In addition, if necessary, a yellow or orange light emitting layer may be further included.

In the organic electroluminescent device of the present application, at least one inner surface of a pair of electrodes, at least one layer selected from a chalcogenide layer, a halogenated metal layer and a metal oxide layer (hereinafter, these are referred to as "surface layers"). ) Is preferable. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of silicon and aluminum on the anode surface of the light emitting medium layer side, and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Driving stability of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide are SiO _X (1 = _X ≦ = 2), AlO _X (1 = _X ≦ = 1.5), SiON, SiAlON, and the like, and preferable examples of the halogenated metal are LiF, MgF ₂ , and CaF _2. , Rare earth fluoride metals, and the like, and preferable examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

A hole injection layer, a hole transport layer or an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. As the hole injection layer, a plurality of layers may be used for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two layers may be used simultaneously. A plurality of layers may also be used for the hole transport layer or the electron blocking layer.

An electron buffer layer, a hole blocking layer, an electron transporting layer or an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. As the electron buffer layer, a plurality of layers may be used for controlling electron injection and improving interface characteristics between the light emitting layer and the electron injection layer, and two layers may be used simultaneously for each layer. A plurality of layers may be used for the hole blocking layer or the electron transporting layer, and a plurality of compounds may be used for each layer.

The light emitting auxiliary layer is a layer located between the anode and the light emitting layer or between the cathode and the light emitting layer. When the light emitting auxiliary layer is located between the anode and the light emitting layer, the light emitting auxiliary layer facilitates the injection and / or transfer of holes or blocks the overflow of electrons. When used for the purpose, or positioned between the cathode and the light emitting layer, it may be used for the purpose of smoothing the injection and / or transfer of electrons or to block the overflow of holes. In addition, the hole auxiliary layer is positioned between the hole transport layer (or the hole injection layer) and the light emitting layer, and may have an effect of smoothing or blocking the hole transfer speed (or injection speed), and thus charge balance. ) Is a layer that can be adjusted. In addition, the electron blocking layer is positioned between the hole transport layer (or the hole injection layer) and the light emitting layer, and blocks the overflow of electrons from the light emitting layer to trap the excitons in the light emitting layer to prevent light leakage. When including two or more layers of the hole transport layer, the additionally included layer may be used for the hole auxiliary layer or the electron blocking layer. The hole auxiliary layer and the electron blocking layer have an effect of improving the efficiency and / or life of the organic EL device.

Moreover, in the organic electroluminescent element of this application, it is also preferable to arrange | position the mixed region of an electron transfer compound and a reducing dopant, or the mixed region of a hole transfer compound and an oxidative dopant on at least one surface of a pair of electrodes. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device that emits white light having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

The organic electroluminescent material according to an example of the present application may be used as a light emitting material for a white organic light emitting device. The white organic electroluminescent device is a side-by-side or stacking method according to an arrangement of R (red), G (green) or YG (yellow green) and B (blue) light emitting units. Various structures have been proposed, such as, or color conversion material (CCM) method. In addition, the organic electroluminescent material according to an example of the present application may be used in an organic electroluminescent device including a quantum dot (QD).

Each layer of the organic electroluminescent device of the present application is a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating, ink jet printing, nozzle printing, slot coating, It may be formed by any one of wet film formation methods such as spin coating, dip coating, and flow coating.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing the material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., in which the solvent is dissolved or dispersed. As long as there is no problem in film-forming property, it may be any.

The present application may provide a display device using a compound represented by Chemical Formula 1 and a composite material for an organic electroluminescent device including the compound represented by Chemical Formula 2. That is, it is possible to manufacture a display device or a lighting device using the composite material for organic electroluminescent elements of this application. Specifically, using the composite material for an organic electroluminescent device of the present application, a display device, for example, a display device for a smartphone, a tablet, a notebook, a PC, a TV or a vehicle, or a lighting device, for example, outdoors or indoors. It is possible to manufacture lighting devices.

Hereinafter, it will be described whether the light emitting efficiency and lifespan characteristics of the OLED device can be improved by including the composite material for an organic EL device of the present application. However, the following examples merely illustrate the characteristics of the OLED device including the composite material for an organic electroluminescent device according to the present application for detailed understanding of the present application, and the present application is not limited to the following examples.

[device Example  1 to 18] organic according to the present application Electric field  Including a composite material for a light emitting device OLED  Device manufacturing

OLED device was manufactured using the composite material for organic electroluminescent devices of this application. First, the transparent electrode ITO thin film (10Ω / □) obtained from OLED glass (manufactured by GeoMatec Co., Ltd.) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol for use. It was. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, the compound HI-1 is put into the cell in the vacuum deposition apparatus, and evacuated until the vacuum in the chamber reaches 10 ^-6 torr, and then a current is applied to the cell. By evaporation to deposit an 80 nm thick first hole injection layer on the ITO substrate. Subsequently, compound HI-2 was placed in another cell in the vacuum deposition equipment, and a second hole injection layer having a thickness of 5 nm was deposited on the first hole injection layer by applying an electric current to the cell to evaporate. Subsequently, Compound HT-1 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was placed in another cell in the vacuum deposition equipment, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer by evaporation by applying a current to the cell. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Into two cells in the vacuum deposition equipment, each of the first host compound and the second host compound shown in Table 1 below as a host, compound D-39 in another cell, and then the two host materials at 1: 1 speed 40 nm thick light emitting layer was deposited on the second hole transport layer by doping the dopant in an amount of 3% by weight relative to the total amount of the host and dopant by simultaneously evaporating the dopant material at different rates. Then, to another cell in two places of the compound ET-1 and Compound EI -1 1: 1 was deposited by evaporation at a rate of the electron transport layer of 35 nm thickness on the light emitting layer. Subsequently, after the compound EI-1 was deposited to a thickness of 2 nm with the electron injection layer, an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED device.

[ Comparative example  1] containing a conventional compound OLED  Device manufacturing

An OLED device was manufactured in the same manner as in Device Example 1, except that Compound A was used as the second host compound.

When the luminous efficiency at 5,000 nit and the current value at 5,000 nit of the OLED device manufactured as described above are constantly applied, the time taken for the first light intensity to be 100% and dropped to 95% ( Lifetime; T95) is shown in Table 1 below.

TABLE 1

From the above Table 1, the organic electroluminescent device comprising a compound represented by the formulas (1) and (2) of the present application as a host, has a high luminous efficiency and improved lifetime characteristics compared to the organic electroluminescent device comprising a conventional organic electroluminescent compound Can be confirmed. By including the composite material for organic electroluminescent elements of the present application, it is possible to improve both efficiency and lifespan characteristics that are in a mutually conflicting relationship in the organic electroluminescent element.

The compounds used in the device examples and comparative examples are shown in Table 2 below.

TABLE 2

Claims (10)

A composite material for an organic electroluminescent device, comprising a compound represented by Formula 1 and a compound represented by Formula 2 below:
[Formula 1]

In Chemical Formula 1,
M is NL- (Ar) _a , S or O,
L is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene,
Ar is 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 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,
Y ₁ to Y ₁₂ are each independently N or CR ₁ ,
R ₁ is 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; Adjacent R _{1 's may} be fused to each other to form a substituted or unsubstituted ring,
a is an integer from 1 to 4, and when a is an integer of 2 or more, each Ar may be the same or different;
[Formula 2]

In Chemical Formula 2,
A ₁ is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl,
L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene,
X ₁ to X ₈ Are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl , -NR ₅ R ₆ or -SiR ₇ R ₈ R _9, or adjacent substituents may be fused to each other to form a ring, provided that any one of X ₁ to X ₈ is substituted or unsubstituted carbazolyl Except
R ₅ to R ₉ are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl , Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3 -30 membered) heteroaryl, or adjacent substituents may be fused to each other to form a ring. The composite material of claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2:
[Formula 1-1] [Formula 1-2]

In Chemical Formulas 1-1 and 1-2,
M and Y ₂ to Y ₁₂ are as defined in claim 1,
Y ₁₃ and Y ₁₄ are each independently the same as the definition of Y ₂ ,
Y ₁ is N or CR ₂ , R ₂ is 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) aryl Silyl, 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. The method according to claim 1, wherein in Formula 1, at least one adjacent pair of Y ₁ to Y ₁₂ is CR ₁ , and R ₁ of the two adjacent CR ₁ are fused to each other to independently represent the following Formulas 1-11 to 1-15 A composite material for an organic electroluminescent device, which forms a ring represented by either:
[Formula 1-11] [Formula 1-12] [Formula 1-13] [Formula 1-14] [Formula 1-15]

In Chemical Formulas 1-11 to 1-15,
X is N or CR ₄ ;
R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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;

Represents a fused portion of the C and R ₁ of the adjacent CR _1. The compound of claim 1, wherein Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted Substituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxali Substituted, unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted Pyrazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuran 1, substitution or ratio Substituted naphthyridinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted benzothienoquinolinyl, substituted or unsubstituted benzofuroquinolinyl, substituted or unsubstituted triadenyl, substituted or (9-25 membered) heteroaryl containing one or more of unsubstituted phenanthroimidazolyl, substituted or unsubstituted nitrogen, oxygen and sulfur, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino Or substituted or unsubstituted fluorenylphenylamino. A composite material for an organic electroluminescent device. The composite material of claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-8:
[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-5] [Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Chemical Formulas 2-1 to 2-8,
A ₁ , L ₁ , and X ₁ to X ₄ are as defined in claim 1,
X ₉ to X ₃₈ are each independently the same as the definition of X ₁ , and b, e, f, g, h and l are each independently 1 or 2, and c, d and i are each independently 1 to 3 Integers, j and k are each independently integers of 1 to 4, and when b to l are integers of 2 or more, each of X ₉ , X ₁₄ , X ₁₉ , X ₂₀ , X ₂₁ , X ₃₀ , X ₃₁ , and X ₃₅ to X ₃₈ may be the same or different from each other,
Z is O or S,
V and W are each a single bond, NR _{16 ,} O or S, provided that both V and W are not a single bond, or both NR ₁₆ ,
R ₁₆ is hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl to be. The method of claim 1, wherein Ar, L, R ₁ , A ₁ , L _{1 ,} X ₁ to X ₈ And substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl (ene), substituted heteroaryl (ene), substituted tree in R ₅ to R ₉ Of alkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, and substituted alkylarylamino Substituents are each independently deuterium; halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C 1 -C 30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-50 membered) heteroaryl unsubstituted or substituted with (C1-C30) alkyl, (C6-C30) aryl or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3- to 50-membered) heteroaryl or tri (C6-C30) arylsilyl; 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; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) ar (C1-C30) alkyl; And (C1-C30) alkyl (C6-C30) aryl. The composite material for an organic electroluminescent device. The composite material of claim 1, wherein the compound represented by Chemical Formula 1 is one or more selected from the following compounds.

The composite material of claim 1, wherein the compound represented by Chemical Formula 2 is one or more selected from the following compounds.

A plurality of host materials comprising a first host material comprising the compound represented by the formula (1) described in claim 1 and a second host material containing the compound represented by the formula (2) according to claim 1. The organic electroluminescent element containing the composite material for organic electroluminescent elements of Claim 1.