KR20200014189A - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to a plurality of host materials including at least one first host compound represented by chemical formula 1 and at least one second host compound represented by chemical formula 2, and an organic electroluminescent device comprising the same. By including the host material according to the present application, an organic electroluminescent device having low driving voltage and/or high efficiency and/or long life characteristics can be manufactured. The chemical formula 1 is HAr-(L_1-Ar_1)_a.

Description

A plurality of host materials and an organic electroluminescent device comprising the same {A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present application relates to a plurality of host materials and organic electroluminescent devices comprising the same.

Electroluminescent devices (EL devices) are self-luminous display devices that have a wide viewing angle, excellent contrast, and fast response speeds. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

An organic electroluminescent device is an element that converts electrical energy into light by applying electricity to an organic light emitting material, and generally has a structure including an anode (anode) and a cathode (cathode) and an organic layer therebetween. The organic material layer of the organic EL device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer (including host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection. Layers and the like. The material used in the organic material layer may be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transporting material, an electron injection material, etc. according to a function. Can be divided. In such an organic EL device, holes are injected from an anode and electrons are injected into a light emitting layer from a cathode by voltage application, and excitons having high energy are formed by recombination of holes and electrons. This energy causes the organic light emitting compound to be in an excited state, and the excited state of the organic light emitting compound returns to the ground state to emit energy as light and emit light.

The light emitting material of the organic electroluminescent device is the most important factor for determining the luminous efficiency of the device. The light emitting material should have high quantum efficiency, high electron and hole mobility, and the light emitting material layer formed should be uniform and stable. Such light emitting materials are divided into blue, green, or red light emitting materials according to light emission colors, and there are also yellow or orange light emitting materials. In addition, the light emitting material may be classified into a host material and a dopant material in terms of function. Recently, the development of high efficiency and long life organic electroluminescent devices has emerged as an urgent task. Especially, considering the EL characteristic level required in medium and large OLED panels, it is urgent to develop a material that is much superior to conventional light emitting materials. It is true. To this end, the desirable properties of the host material, which acts as a solvent and energy carrier in the solid state, should be of high purity and have a suitable molecular weight to enable vacuum deposition. In addition, the high glass transition temperature and thermal decomposition temperature ensure thermal stability, high electrochemical stability is required for long life, easy to form amorphous thin film, good adhesion with other adjacent materials, It is preferable not to.

The luminescent material may be used by mixing a host and a dopant to improve color purity, luminous efficiency and stability. In general, an element having excellent EL characteristics is a structure including a light emitting layer made by doping a dopant to a host. When using such a dopant / host material system, the host material has a great impact on the efficiency and lifetime of the light emitting device, so its selection is important.

Korean Patent Laid-Open Publication No. 2018-0012709 discloses a compound of a fused structure including indolocarbazole and azepine as a host material, but specifically discloses a plurality of host materials in a specific combination as in the present invention. Not.

Korean Unexamined Patent Publication No. 2018-0012709 (published Feb. 06, 2018)

SUMMARY OF THE INVENTION An object of the present invention is to firstly provide a plurality of types of host materials capable of producing organic electroluminescent devices having low drive voltages and / or high luminous efficiency and / or long lifetime characteristics. It is to provide an organic electroluminescent device comprising.

As a result of intensive studies to solve the above technical problem, the present inventors have provided a plurality of types of hosts including at least one first host compound represented by the following Formula 1 and at least one second host compound represented by the following Formula 2. The present invention has been accomplished by finding that the material achieves the above-mentioned object.

[Formula 1]

HAr- (L ₁ -Ar ₁ ) _a

In Chemical Formula 1,

HAr is a substituted or unsubstituted nitrogen containing (3-10 membered) heteroaryl;

L ₁ is a single bond or a substituted or unsubstituted (C6-C30) arylene;

Ar ₁ is substituted or unsubstituted (C6-C30) aryl;

a is an integer of 1 to 3, and when a is an integer of 2 or more, each of (L ₁ -Ar ₁ ) may be the same as or different from each other,

[Formula 2]

In Chemical Formula 2,

L ₂ is a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C3-C30) cycloalkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted Ringed (3- to 30-membered) heteroarylene;

Ar is hydrogen, deuterium, halogen, cyano, 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, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₁₆ R ₁₇ or -SiR ₁₈ R ₁₉ R ₂₀ ; May be linked to an adjacent substituent to form a ring;

R ₁₆ to R ₂₀ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

는 하기 화학식 2-1 또는 화학식 2-2로 나타내고;

Is represented by the following Chemical Formula 2-1 or Chemical Formula 2-2;

 [Formula 2-1] [Formula 2-2]

In Chemical Formulas 2-1 and 2-2,

X ₁ to X ₂₅ are each independently N or CR _a ;

R _a is each independently 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 Substituted 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; It may be linked to an adjacent substituent to form a ring.

By using the plurality of types of host materials according to the present invention, it is possible to manufacture organic electroluminescent devices having low driving voltage and / or high luminous efficiency and / or long lifetime characteristics.

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

The present application relates to a plurality of host materials including at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2, and an organic electroluminescent device including the host materials. will be.

As used herein, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device, and may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, Electron transfer material, electron injection material, and the like.

As used herein, "plural species of host material" means a host material comprising a combination of two or more compounds that may be included in any light emitting layer constituting the organic electroluminescent device, and includes (eg, For example, it can 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 or may be included in different light emitting layers through methods used in the art. For example, the two or more compounds may be mixed or co-deposited or deposited separately.

As used herein, "(C1-C30) alkyl (ene)" means a straight or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein 1 to 20 carbon atoms is preferable, and 1 to 10 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 (ene)" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein 3 to 20 carbon atoms are preferable, and 3 to 7 carbon atoms are more preferable. desirable. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. As used herein, "(C3-C30) cycloalkenyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms and including a double bond in its ring skeleton, and preferably 3 to 20 carbon atoms. It is more preferable that it is 3-7. Examples of the cycloalkenyl include cyclopropenyl, cyclobutenyl, cyclopentenyl, and the like. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7 ring skeleton atoms, and is a group consisting of B, N, O, S, Si and P, preferably O It means a cycloalkyl containing at least one heteroatom selected from the group consisting of S, and 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 and includes a spiro structure. It is preferable that the said ring skeleton carbon number is 6-20, and it is more preferable that it is 6-15. Specific examples of the aryl include phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, vinaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, di Phenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl , Pyrenyl, tetrasenyl, peryllenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl ( cumenyl), spiro [fluorene-fluorene] yl, spiro [fluorene-benzofluoren] yl, azulenyl and the like. More specifically, examples of the aryl include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p- (2-phenylpropyl) phenyl, 4'-methylbiphenyl, 4 "-t-butyl-p-terphenyl-4-yl, o- Biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl- 4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3 -Fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-flu Orenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3- Fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenan Tril, 9-phenanthryl, 1-Chrisnil, 2-Chrisnil, 3-Cry Neyl, 4-Chrisnyl, 5-Chrisnyl, 6-Crissenyl, Benzo [c] phenanthryl, Benzo [g] Crissenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4 -Triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, etc. Herein, " (3- to 30-membered) heteroaryl (Len) "means an aryl group having 3 to 30 ring skeleton atoms and including one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge, wherein the ring skeleton atoms Preferably, the number is 5 to 25. The number of heteroatoms is preferably 1 to 4, and may be monocyclic or a fused ring system condensed with one or more benzene rings, and may be partially saturated. Deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or Substituted (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) One or more substituents selected from the group consisting of alkyl (C 6-30) arylamino may be bonded. In addition, the heteroaryl herein includes a form in which one or more heteroaryl groups or aryl groups are linked to a heteroaryl group by a single bond, and those having a spiro structure. As examples of the heteroaryl, specifically, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetra Monocyclic heteroaryl such as genyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, Dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadia Zolyl, quinolyl, isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenantridinyl, benzodioxolyl, indole Ridgedinyl, acridinyl, silafluorenyl, crab Fused ring systems, such as town flow alkylenyl, and the like heteroaryl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyri Midinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazine- 2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolidininyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl , 7-indolidininyl, 8-indolidininyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopi Ridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoin Doryl, 2-isoindoleyl, 3-isoindoleyl, 4-isoindoleyl, 5-isoindoleyl, 6-isoindoleyl, 7-isoindoleyl, 2-furyl, 3-furyl, 2-benzofura Nyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6- Benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofura Neyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4 Isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carba Zolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazole- 4-day, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthryldinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1- Acridinyl, 2-acridinyl, 3-arc Diyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxazozolyl, 5-oxazozolyl, 3-furazanyl, 2-thienyl , 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl , 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3- (2-phenylpropyl) pyrrole-1 -Yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-di Benzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silaflu Orenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl Etc. can be mentioned. "Halogen" herein includes F, Cl, Br and I atoms.

In addition, "ortho (o)", "meta (m)", and "para (p)" are prefixes indicating relative positions of substituents, respectively. The ortho position indicates that two substituents are adjacent to each other, for example, 1 and 2 positions in a benzene substituent, and the meta position indicates that two substituents are in positions 1 and 3, for example. The benzene substituent means 1, 3 digits, and the para position indicates that two substituents are located at 1,4 position, and for example, 1, 4 digits in the benzene substituent.

As used herein, a ring formed by linking with an adjacent substituent is a ring of substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic, aromatic, or combinations thereof formed by linking or fusing two or more adjacent substituents It may be a ring of a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic or a combination thereof. The ring formed may also comprise one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to an example of the present application, the ring formed by connecting with the adjacent substituent is a (5- to 20-membered) polycyclic aromatic ring, which may include one or more heteroatoms selected from N, O, and S.

In addition, in the description of "substituted or unsubstituted", "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. (C1-C30) alkyl (lene), substituted (C6-C30) aryl substituted at HAr, L ₁ , Ar ₁ , L ₂ , Ar, R ₁₆ to R ₂₀ , and R _a of the present Formula 1 and Formula 2 (Ene), substituted (3- to 30-membered) heteroaryl (ene), substituted (C3-C30) cycloalkyl (ene), substituted (C3-C30) cycloalkenyl, substituted (3- to 7-membered) Heterocycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl, substituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) arylamino, and Substituents of substituted (C1-C30) alkyl (C6-C30) arylamino are each independently 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, Heterocyclo Substituted with (5- to 30-membered) heteroaryl, (5- to 30-membered) heteroaryl unsubstituted or substituted with Kyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl, or Unsubstituted (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, mono- or di- (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl, (C1 -C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboroyl, Di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, and (C1-C30) alkyl (C6- One or more selected from the group consisting of aryl, for example, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, Or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted diphenylamino, or substituted or unsubstituted Phenylbiphenylamino.

Hereinafter, a host material according to an embodiment will be described.

The host material according to the present invention includes at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2, and is included in the light emitting layer of the organic electroluminescent device according to an example. Can be.

A first host compound, which is a host material according to one embodiment, may be represented by Formula 1 below.

[Formula 1]

HAr- (L ₁ -Ar ₁ ) _a

In Chemical Formula 1,

HAr is a substituted or unsubstituted nitrogen containing (3-10 membered) heteroaryl;

L ₁ is a single bond or a substituted or unsubstituted (C6-C30) arylene;

Ar ₁ is substituted or unsubstituted (C6-C30) aryl;

a is an integer of 1 to 3, and when a is an integer of 2 or more, each of (L ₁ -Ar ₁ ) may be the same as or different from each other.

In one example, HAr may be a substituted or unsubstituted nitrogen-containing (5- to 10-membered) heteroaryl, and preferably, an unsubstituted nitrogen-containing (6- to 10-membered) heteroaryl. For example, HAr can be pyrimidinyl, triazinyl, quinolinyl, quinoxalinyl, or quinazolinyl.

For example, L ₁ may be a single bond or a substituted or unsubstituted (C6-C25) arylene, and preferably a single bond or an unsubstituted (C6-C20) arylene. For example, L ₁ is phenylene, m-biphenylene, p-biphenylene, naphthylene, phenyl substituted or unsubstituted or substituted with a single bond, naphthyl or fluorenyl. Or benzofluorenylene unsubstituted or substituted with phenyl.

For example, Ar ₁ may be substituted or unsubstituted (C6-C25) aryl, preferably (C6-C18) arylyl unsubstituted or substituted with (C1-C6) alkyl or (C6-C18) aryl. Can be. For example, Ar ₁ is phenyl, m-biphenyl, p-biphenyl, naphthyl, m-terphenyl, p-terphenyl, triphenylenyl, phenanthrenyl, unsubstituted or substituted with fluorenyl, at least Fluorenyl substituted with one phenyl or methyl (eg phenylfluorenyl, diphenylfluorenyl or dimethylfluorenyl), or benzofluorenyl substituted with at least one phenyl or methyl (eg dimethylbenzo Fluorenyl or diphenylbenzofluorenyl).

As an example, a may be an integer of 2 or 3, wherein each of (L ₁ -Ar ₁ ) may be the same as or different from each other.

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 Chemical Formulas 1-1 and 1-2,

Y ₁ to Y ₆ and Z ₁ to Z ₄ are each independently CR ₄ or N, at least one of Y ₁ to Y ₆ is N, and Z ₁ to Z ₄ At least one of is N;

Each R ₄ is independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C6-C30) aryl; May be linked to an adjacent substituent to form a ring;

L ₁ , Ar ₁ , and a are as defined in Formula 1.

For example, at least one of Y ₁ to Y ₆ of Formula 1-1 may be N, preferably at least two of Y ₁ to Y ₆ may be N, and more preferably at least three of Y ₁ to Y ₆ May be N. For example, the compound represented by Formula 1-1 may be pyrimidine or triazine substituted with (L ₁ -Ar ₁ ) _a .

For example, Z ₁ to Z ₄ of Chemical Formula 1-2 At least one of is N, preferably at least two of Z ₁ to Z ₄ may be N. For example, the compound represented by Formula 1-2 may be quinoline, quinoxaline, or quinazoline, in which (L ₁ -Ar ₁ ) _a is substituted.

In one embodiment, each R ₄ is independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C2-C20) alkenyl, or substituted or unsubstituted (C6-C18) aryl ; Two adjacent R _{4 's} may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic ring, and preferably hydrogen or two adjacent R ₄ ' s are connected to each other and are unsubstituted (3-18 membered) monocyclic or polycyclic ring can be formed, more preferably hydrogen or two adjacent R ₄ are connected to each other to form an unsubstituted (3-10 membered) monocyclic ring Can be. For example, R ₄ may be each independently hydrogen or two adjacent R ₄ may be fused to each other to form an unsubstituted benzene ring.

According to an example, the first host compound represented by Chemical Formula 1 may be exemplified as the following compound, but is not limited thereto.

The compound represented by Formula 1 of the present application may be prepared by a synthesis method known to those skilled in the art. For example, the compound represented by Formula 1-1 or 1-2 may be synthesized by referring to Scheme 1 or 2 below. It is not limited to this.

Scheme 1

Scheme 2

In Reaction Schemes 1 and 2, L ₁ , Ar ₁ and a are as defined in Formula 1, and Y ₁ to Y ₆ and Z ₁ to Z ₄ are as defined in Formulas 1-1 and 1-2.

Exemplary synthesis examples of the compound which may be represented by Formula 1-1 or Formula 1-2 according to the above-described examples, all of them are Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction, Pd (II) -catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, And it will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Chemical Formulas 1-1 or 1-2 are combined in addition to the substituents specified in the specific synthesis examples based on the Phosphine-mediated reductive cyclization reaction.

Another host material according to one embodiment, the second host compound may be represented by the following formula (2).

[Formula 2]

In Chemical Formula 2,

L ₂ is a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3- to 30-membered) heteroarylene, or substituted or Unsubstituted (C3-C30) cycloalkylene;

Ar is hydrogen, deuterium, halogen, cyano, 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, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₁₆ R ₁₇ or -SiR ₁₈ R ₁₉ R ₂₀ ; May be linked to an adjacent substituent to form a ring;

R ₁₆ to R ₂₀ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

는 하기 화학식 2-1 또는 화학식 2-2로 나타내고;

Is represented by the following Chemical Formula 2-1 or Chemical Formula 2-2;

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

In Chemical Formulas 2-1 and 2-2,

X ₁ to X ₂₅ are each independently N or CR _a ;

R _a is each independently 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 Substituted 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; It may be linked to an adjacent substituent to form a ring.

For example, L ₂ may be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (5- to 25-membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or Unsubstituted (5- to 18-membered) heteroarylene. For example, L ₂ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted p-biphenyl Lene, substituted or unsubstituted naphthylene, or substituted or unsubstituted carbazolylene.

In one example, Ar may be hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl, preferably hydrogen, deuterium, substituted or unsubstituted It may be a (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- 18-membered) heteroaryl.

Specifically, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, Substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or Unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzo Naphthothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo Fluorenyl, substituted or unsubstituted spirobiflu Lenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted naphthylphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted dibiphenylamino, Substituted or unsubstituted biphenylfluorenylamino, or substituted or unsubstituted biphenyldibenzofuranylamino, for example, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, Substituted or unsubstituted p-terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Benzofluorenyl, substituted or unsubstituted Hwandoen RY lobby fluorenyl, and may be substituted or unsubstituted diphenylamino, substituted or unsubstituted phenyl-amino-biphenyl, or a substituted or unsubstituted naphthyl phenylamino.

는 하기 화학식 2-1로 나타낼 수 있다. According to one embodiment, of Formula 2

May be represented by the following Chemical Formula 2-1.

[Formula 2-1]

In Chemical Formula 2-1,

X ₁ to X ₁₂ are each independently N or CR _a ;

R _a is each independently 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 Substituted 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; It may be linked to an adjacent substituent to form a ring.

In one embodiment, each R _a is independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or may be linked to an adjacent substituent to form a ring, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl or adjacent substituents may be linked or fused to form a ring of a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof, more preferably Is hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or adjacent substituents are linked or fused to form a substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aromatic ring or a combination thereof Can be formed. For example, R _a may each independently be hydrogen or substituted or unsubstituted phenyl, or may be fused to each other to form a substituted or unsubstituted aromatic ring.

For example, X ₁ and X ₂ are each independently CR _a, wherein R _a may be fused to each other to form a benzene ring.

Specifically, Formula 2-1 according to an example may be represented by the following Formula 2-1-1.

[Formula 2-1-1]

In Chemical Formula 2-1-1,

R ₄₁ to R ₄₃ 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; May be linked to an adjacent substituent to form a ring;

ba is an integer from 1 to 3, bb is an integer from 1 to 4, bc is an integer from 1 to 5, and ba, bb and bc are integers of 2 or more, each R ₄₁ , each R ₄₂ and each R ₄₃ may be the same or different.

For example, R ₄₁ to R ₄₃ may be each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or may be linked to an adjacent substituent to form a ring, preferably hydrogen, deuterium, substituted or Unsubstituted (C6-C25) aryl or adjacent substituents may be linked or fused to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof, More preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or adjacent substituents connected or fused to substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aromatics, or a combination thereof Can form a ring. For example, R ₄₁ to R ₄₃ may each independently be hydrogen or substituted or unsubstituted phenyl or may be fused with each other to form a substituted or unsubstituted aromatic ring.

는 하기 화학식 2-2로 나타낼 수 있다. According to another example, of Formula 2

May be represented by the following Chemical Formula 2-2.

[Formula 2-2]

In Chemical Formula 2-2,

X ₁₃ to X ₂₅ are each independently N or CR _a ;

R _a is each independently 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 Substituted 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; It may be linked to an adjacent substituent to form a ring.

In one embodiment, each R _a is independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or may be linked to an adjacent substituent to form a ring, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl or adjacent substituents may be linked or fused to form a ring of a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof, more preferably Is hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or adjacent substituents are linked or fused to form a substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aromatic ring or a combination thereof Can be formed. For example, R _a may each independently be hydrogen or substituted or unsubstituted phenyl, or may be fused to each other to form a substituted or unsubstituted aromatic ring.

For example, X ₁₅ and X ₁₆ are each independently CR _a, wherein R _a may be fused to each other to form a benzene ring.

For example, X ₁₇ And X ₁₈ are each independently CR _a, wherein R _a may be fused to each other to form a benzene ring.

Specifically, Formula 2-2 according to an example may be represented by the following Formula 2-2-1.

[Formula 2-2-1]

In Chemical Formula 2-2-1,

R ₃₁ to R ₃₄ 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; May be linked to an adjacent substituent to form a ring;

aa is an integer of 1 to 3, ab and ac are each independently an integer of 1 to 4, ad is 1 or 2, each a ₃₁ , when aa, ab, ac and ad is an integer of 2 or more, respectively R ₃₂ , each R ₃₃ and each R ₃₄ may be the same or different.

In one example, R ₃₁ to R ₃₄ are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or may be linked to an adjacent substituent to form a ring, preferably hydrogen, deuterium, substituted or Unsubstituted (C6-C25) aryl or adjacent substituents may be linked or fused to form a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof, More preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, or adjacent substituents connected or fused to substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aromatics, or a combination thereof Can form a ring. For example, R ₄₁ to R ₄₃ may each independently be hydrogen or substituted or unsubstituted phenyl or may be fused with each other to form a substituted or unsubstituted aromatic ring.

According to an example, the second host compound represented by Chemical Formula 2 may be more specifically exemplified as the following compound, but is not limited thereto.

The compound of formula 2 according to the present application, specifically, the compound of formula 2-1 may be synthesized with reference to the method disclosed in Korean Patent Application No. 2018-0021961 (filed February 23, 2018), and the compound of formula 2-2 It may be synthesized with reference to the method disclosed in Korean Patent Publication No. 2018-0012709 (published Feb. 06, 2018), but is not limited thereto, and may be prepared by other synthetic methods known to those skilled in the art.

Hereinafter, the organic electroluminescent element to which the above-mentioned multiple kind of host material is applied is demonstrated.

An organic electroluminescent device according to one embodiment includes a first electrode; Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is represented by at least one first host compound represented by Formula 1 and Formula 2 And a host material comprising at least one second host compound.

In some embodiments, the first host compound represented by Formula 1 and the second host compound represented by Formula 2 may be included in the same organic material layer, or may be included in different organic material layers, respectively.

The light emitting layer may be a single layer as a light emitting layer, or may be a plurality of layers in which two or more layers are stacked. 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, preferably less than 17% by weight.

One of the first electrode and the second electrode may be an anode (anode) and the other may be a cathode (cathode). In this case, the first electrode and the second electrode may be formed of a transparent conductive material or a transflective or reflective conductive material, respectively. According to the type of material forming the first electrode and the second electrode, the organic EL device may be a top emission type, a bottom emission type or a double-sided emission type. The organic material layer 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 injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer in addition to the light emitting layer. It may further comprise more than a layer.

The organic layer may further include an amine compound and / or a azine compound in addition to the light emitting material of the present application. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light emitting layer, light emitting auxiliary layer, or electron blocking layer is an amine compound, for example, an arylamine compound, a styrylarylamine compound, etc. It may be included as an injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emission auxiliary material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer and the hole blocking layer may include a azine compound as an electron transport material, an electron injection material, an electron buffer material and a hole blocking material.

In addition, the organic material layer is one or more metals selected from the group consisting of Group 1, Group 2, 4 cycle transition metal, 5 cycle transition metal, lanthanide-based metal and d- transition element, or at least one containing such metal It may further include a complex compound.

The organic electroluminescent material according to one embodiment 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 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 may be used in an organic electroluminescent device including a quantum dot (QD).

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. 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. The hole injection layer may also be doped with p-dopant. The electron blocking layer may be located between the hole transport layer (or the hole injection layer) and the light emitting layer, and may block the overflow of electrons from the light emitting layer to trap the excitons in the light emitting layer to prevent light leakage. As the hole transport layer or the electron blocking layer, a plurality of layers may be used, and a plurality of compounds may be used for each 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. In addition, the electron injection layer may be doped with n-dopant.

The light emitting auxiliary layer is positioned between the anode and the light emitting layer or between the cathode and the light emitting layer. When the light emitting auxiliary layer is positioned between the anode and the light emitting layer, the injection and / or transfer of holes may be smooth or electrons may be formed. It may be used for blocking overflow, and when the light emitting auxiliary layer is positioned between the cathode and the light emitting layer, it may be used for smoothing the injection and / or transfer of electrons or blocking the overflow of holes. In addition, the hole auxiliary layer may be positioned between the hole transport layer (or the hole injection layer) and the light emitting layer, and may exhibit an effect of smoothing or blocking the hole transfer speed (or injection speed), and thus, charge balance. ) Can be adjusted. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layer further included may be used for the use of a hole auxiliary layer or an electron blocking layer. The light emission auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and / or lifespan of the organic EL device.

In the organic electroluminescent device of the present application, on 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 on the light emitting medium layer side and a metal halide layer or metal oxide layer on the cathode surface on 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 include SiO _X (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON, SiAlON, and the like, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

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 electrode. In this way, the electron transfer compound is reduced to an anion, thereby facilitating the 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 deliver 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, by using a reducing dopant layer as a charge generating layer, it is possible to manufacture an organic electroluminescent device having white light emission having two or more light emitting layers.

The organic electroluminescent device according to an example may further include one or more dopants in the emission layer.

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), 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 Formula 101,

L is selected from the following structures 1 or 2;

[Structure 1] [Structure 2]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6 -C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₀ to R ₁₀₃ may be linked to each other to form a substituted or unsubstituted fused ring with adjacent substituents, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzo Thienopyridine, 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, (C1-C30) alkyl unsubstituted or substituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6 -C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₄ to R ₁₀₇ may have adjacent substituents connected to each other to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted di Benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine is possible;

R ₁₁₁ to R ₁₂₁ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted ( C6-C30) aryl, wherein adjacent substituents are linked to each other to form a substituted or unsubstituted fused ring;

s is an integer of 1-3.

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

Formation of 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, Any one of wet film forming methods such as spin coating, dip coating, and flow coating can be applied. In the case of the wet film forming 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, and the like, in which the material forming each layer is dissolved or dispersed. As long as there is no problem in film-forming property, it may be any.

When forming the host compound and the dopant compound according to one embodiment, the process by co-deposition or mixed deposition.

The co-deposition is a method in which two or more isomeric materials are placed in each individual crucible source, and two cells are simultaneously applied to simultaneously evaporate the material to evaporate the material, and the mixed deposition is two or more isomeric materials before deposition. After mixing in the crucible source, a current is applied to one cell to evaporate and deposit the material.

According to one embodiment, the present invention uses an organic electroluminescent device to display devices, for example, display devices for smartphones, tablets, notebooks, PCs, TVs or vehicles, or lighting devices, for example outdoors or An indoor lighting device can be provided.

Hereinafter, a method of manufacturing an organic electroluminescent device including a plurality of host materials according to the present application and its characteristics will be described for a detailed understanding of the present application.

 [device Example  1 to 8] depositing a first host compound and a second host compound according to the present application as a host OLED  Produce

OLEDs comprising the compounds according to the invention were prepared. First, a transparent electrode ITO thin film (10 μs / □) obtained from an OLED glass (manufactured by GeoMatec Co., Ltd.) was subjected to ultrasonic cleaning using acetone, ethanol, and distilled water sequentially, and then stored in isopropanol and used. 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. And evaporated 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 apparatus, and a second hole injection layer having a thickness of 5 nm was deposited on the first hole injection layer by evaporation by applying a current to the cell. Subsequently, Compound HT-1 was placed in a cell in a vacuum deposition apparatus, 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 a cell in a vacuum deposition apparatus, the first host compound and the second host compound shown in Table 1 below as a host, compound RD-39 as a dopant in another cell, and then the two materials were evaporated at a rate of 1: 1. 40 nm thick light emitting layer was deposited on the hole transport layer by doping in an amount of 3% by weight. Then, addition of other cells Compound ET-1 and Compound EI -1 in two places 1: 1 was deposited by evaporation at a rate of the electron transport layer of 35nm thickness on the light emitting layer. Subsequently, Compound EI- 1 was deposited on the electron transport layer with a thickness of 2 nm as an electron injection layer, and then an Al cathode was deposited on the electron injection layer with a thickness of 80 nm using another vacuum deposition equipment to manufacture an OLED.

[ Comparative example  1 and 2] comprising compounds not according to the present OLED  Produce

An OLED was manufactured in the same manner as in the device example, except that the compound of Table 1 was used as the host.

As described above, the driving voltage, luminous efficiency, power efficiency, and light intensity of the organic light emitting diodes of Examples 1 to 8 and Comparative Examples 1 and 2 based on the 5,000 nits luminance are reduced from 100% to 80%. Time (life; T80) is shown in Table 1 below.

TABLE 1

From Table 1, it can be seen that the organic electroluminescent device including a specific combination of compounds according to an example as a host material has improved driving voltage, efficiency, and / or lifespan as compared to the conventional organic electroluminescent device.

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

TABLE 2

Claims (8)

A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula (1), and the second host compound is represented by the following formula (2) Host material:
[Formula 1]
HAr- (L ₁ -Ar ₁ ) _a
In Chemical Formula 1,
HAr is a substituted or unsubstituted nitrogen containing (3-10 membered) heteroaryl;
L ₁ is a single bond or a substituted or unsubstituted (C6-C30) arylene;
Ar ₁ is substituted or unsubstituted (C6-C30) aryl;
a is an integer of 1 to 3, and when a is an integer of 2 or more, each of (L ₁ -Ar ₁ ) may be the same or different from each other;
[Formula 2]

In Chemical Formula 2,
L ₂ is a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C3-C30) cycloalkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted Ringed (3- to 30-membered) heteroarylene;
Ar is hydrogen, deuterium, halogen, cyano, 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, substituted or unsubstituted (3-30 membered) heteroaryl, -NR ₁₆ R ₁₇ or -SiR ₁₈ R ₁₉ R ₂₀ ; May be linked to an adjacent substituent to form a ring;
R ₁₆ to R ₂₀ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

Is represented by the following Chemical Formula 2-1 or Chemical Formula 2-2;
[Formula 2-1] [Formula 2-2]

In Chemical Formulas 2-1 and 2-2,
X ₁ to X ₂₅ are each independently N or CR _a ;
R _a is each independently 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 Substituted 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; It may be linked to an adjacent substituent to form a ring. The host material of claim 1, wherein Formula 1 is represented by the following Formula 1-1 or 1-2:
[Formula 1-1] [Formula 1-2]

In Chemical Formulas 1-1 and 1-2,
Y ₁ to Y ₆ And Z ₁ to Z ₄ are each independently CR ₄ or N, at least one of Y ₁ to Y ₆ is N, and Z ₁ to Z ₄ At least one of is N;
Each R ₄ is independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C6-C30) aryl; May be linked to an adjacent substituent to form a ring;
L ₁ , Ar ₁ , and a are as defined in claim 1. The host material of claim 1, wherein Formula 2-1 is represented by the following Formula 2-1-1:
[Formula 2-1-1]

In Chemical Formula 2-1-1,
R ₄₁ to R ₄₃ 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; May be linked to an adjacent substituent to form a ring;
ba is an integer from 1 to 3, bb is an integer from 1 to 4, bc is an integer from 1 to 5, and ba, bb and bc are integers of 2 or more, each R ₄₁ , each R ₄₂ and each R ₄₃ may be the same or different. The host material of claim 1, wherein Formula 2-2 is represented by the following Formula 2-2-1:
[Formula 2-2-1]

In Chemical Formula 2-2-1,
R ₃₁ to R ₃₄ 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; May be linked to an adjacent substituent to form a ring;
aa is an integer of 1 to 3, ab and ac are each independently an integer of 1 to 4, ad is 1 or 2, each a ₃₁ , when aa, ab, ac and ad is an integer of 2 or more, respectively R ₃₂ , each R ₃₃ and each R ₃₄ may be the same or different. The method of claim 1, wherein in Formula 2, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or Unsubstituted p-biphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted P-terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothio Phenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted fluore Nil, substituted or unsubstituted benzofluorenyl, substituted or Substituted spirobifluorenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted naphthylphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted Host material, which is substituted dibiphenylamino, substituted or unsubstituted biphenylfluorenylamino, or substituted or unsubstituted biphenyldibenzofuranylamino. The host material of claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

The host material of claim 1, wherein the compound represented by Formula 2 is selected from the following compounds.

An organic electroluminescent element comprising an anode, a cathode, and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of host materials according to claim 1.