KR20160060569A - A plurality of host materials and an organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to multiple host materials and an organic electroluminescence device comprising the same. According to the present invention, it is possible to obtain an organic electroluminescence device having significantly improved service life in combination with excellent current efficiency and power efficiency by using multiple host compounds, as compared to the conventional device using a single host compound. The host compounds comprise a first host compound represented by the following chemical formula 1 and a second host compound represented by the following chemical formula 2. In chemical formulae 1 and 2, each of Ar_1, L_1, R_1-R_8 and R_11-R_18 is the same as defined in the specification.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an organic electroluminescent device including a plurality of host materials and an organic electroluminescent device including the host material.

The present invention relates to a plurality of kinds of host materials and an organic electroluminescent device including the same.

An electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company first developed an organic electroluminescent device using an aromatic diamine and an aluminum complex having low molecular weight as a material for forming a light emitting layer (Appl. Phys. Lett. 51, 913, 1987].

BACKGROUND ART An organic electroluminescence device (OLED) is an element that converts electric energy into light by applying electricity to an organic light emitting material. The organic electroluminescence device usually has a structure including an anode (anode) and a cathode and an organic layer therebetween. The organic material layer of the organic electroluminescent device may include a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer (including a host and a dopant material), an electron buffer layer, a hole blocking layer, an electron transporting layer, The material used for the organic material layer is classified into a hole injecting material, a hole transporting material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transporting material, and an electron injecting material. In such an organic electroluminescent device, holes are injected from the anode into the light emitting layer, electrons from the cathode are injected into the light emitting layer, and excitons with high energy are formed by recombination of holes and electrons. This energy causes the light-emitting organic compound to be in an excited state, and the excited state of the light-emitting organic compound is returned to the ground state, and energy is emitted to the light to emit light.

The luminescent material of the organic electroluminescent device is the most important factor for determining the luminescent efficiency of the device. The luminescent material should have a high quantum efficiency and a high mobility of electrons and holes, and the formed luminescent material layer should be uniform and stable. Such a light emitting material is divided into a blue, green or red light emitting material depending on a luminescent color, and further, there is a yellow or orange light emitting material. Further, the luminescent material can be divided into a host material and a dopant material in terms of function. Recently, development of a high efficiency and long-life organic electroluminescent device has emerged as an urgent task. Especially, in consideration of the EL characteristic level required for a medium to large-sized OLED panel, it is urgent to develop a material superior to the conventional luminescent material . For this purpose, the desirable characteristics of the host material acting as a solid state solvent and energy transfer agent should be high purity and have a proper molecular weight to enable vacuum deposition. In addition, the glass transition temperature and thermal decomposition temperature must be high to ensure thermal stability, high electrochemical stability is required for longevity improvement, amorphous thin film must be easy to form, and adhesion to other adjacent layers is good, You should not.

The light emitting material can be used by mixing a host and a dopant to improve color purity, luminescence efficiency and stability. In general, a device having excellent EL characteristics is a structure including a light emitting layer made by doping a host with a dopant. When using such a dopant / host material system, the selection is important because the host material has a significant effect on the efficiency and lifetime of the light emitting device.

JP-A-2014-160813 A2 discloses an organic electroluminescent device comprising a nitrogen-containing heteroaryl compound in which pyrrole, aromatic aryl and 7-membered aryl are condensed as a host / dopant material, Of an organic electroluminescent device using only a host of the present invention. However, this document does not disclose specifically an organic electroluminescent device using a nitrogen-containing specific heteroaryl derivative and a plurality of kinds of hosts containing a nitrogen-containing heteroaryl and a specific carbazole derivative directly or through arylene.

The present inventors have found that, in contrast to the use of one kind of host in the light-emitting layer, when a plurality of kinds of hosts including a nitrogen-containing specific heteroaryl derivative and a specific carbazole derivative directly connected with nitrogen-containing heteroaryl or arylene is used And that the organic electroluminescent device including the organic electroluminescent device has high efficiency and a long lifetime, thereby completing the present invention.

Japanese Laid-Open Patent Publication JP 2014-160813 A2 (issued April 9, 2014)

An object of the present invention is to provide an organic electroluminescent device having high efficiency and long life.

As a result of studying the above problems, the present inventors have found that the present inventors have found that a light emitting device comprising at least one light emitting layer between an anode and a cathode, wherein the light emitting layer comprises a host and a phosphorescent dopant, At least a first host compound of a plurality of kinds of host compounds is represented by the following formula 1 and a second host compound is represented by the following formula 2 to find out that the organic electroluminescent device achieves the above- .

[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,

Ar ₁ is substituted or unsubstituted (3-30 membered) heteroaryl;

L ₁ is a single bond or substituted or unsubstituted (C 6 -C 30) arylene;

R ₁ to R ₈ and R ₁₁ to R ₁₈ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) alkoxy, substituted or unsubstituted tri (C1-C30) (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6- C30) alkyl (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring which is connected to each other to form a substituted or unsubstituted monocyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is a Lt; / RTI > or more heteroatoms;

Wherein said heteroaryl comprises one or more heteroatoms selected from B, N, O, S, Si and P;

According to the present invention, an organic electroluminescent device having high efficiency and long life is provided, and a display device or a lighting device using the same can be manufactured.

The present invention will be described in more detail below, but this should not be construed as limiting the scope of the invention for the purpose of illustration.

The organic electroluminescent device comprising the organic electroluminescent compound represented by the above formulas (1) and (2) will now be described in more detail.

R ₁ to R ₈ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) alkoxy, substituted or unsubstituted tri (C1- (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, ) Alkyl (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, the carbon atom of the alicyclic or aromatic ring being formed may be a substituted or unsubstituted monocyclic or polycyclic Substituted or unsubstituted (C6-C20) aryl, or substituted or unsubstituted (10-30 membered) heteroaryl, or may be linked to each other to form a substituted or nonsubstituted (C6-C12) monocyclic or polycyclic aromatic ring, more preferably each independently hydrogen; (C6-C15) aryl unsubstituted or substituted with (C1-C6) alkyl or tri (C6-C12) arylsilyl; (10-25) heteroaryl substituted by (C6-C20) aryl; Or an unsubstituted (20-30 membered) heteroaryl or may be connected to form an unsubstituted (C6-C12) monocyclic aromatic ring, for example, each independently hydrogen; Phenyl substituted or unsubstituted with triphenylsilyl; Fluorenyl substituted by methyl; Carbazole unsubstituted or substituted with (C6-C20) aryl substituted or unsubstituted with a substituent selected from the group consisting of cyano, (C1-C6) alkyl, (C6-C18) aryl and triphenylsilyl; Benzocarbazole substituted with phenyl; Dibenzocarbazole substituted with phenyl; Or a nitrogen-containing (20-30 membered) heteroaryl, or they may be connected to form benzene.

R ₁ to R ₈ in Formula 1 may be independently selected from the following structures.

Wherein L is a substituted or unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (5-20 membered heteroarylene), preferably unsubstituted (C6-C18) Is preferably unsubstituted (C6-C10) arylene, and can be, for example, phenyl;

n is an integer from 0 to 2, preferably 0 or 1;

R ₂₁ to R ₂₅ and R ₃₁ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, the carbon atom of the alicyclic or aromatic ring being formed may be a substituted or unsubstituted monocyclic or polycyclic And preferably each independently hydrogen or substituted or unsubstituted (C6-C20) aryl, more preferably each independently hydrogen; Or (C6-C20) aryl which is unsubstituted or substituted by cyano, (C1-C6) alkyl, (C6-C18) aryl or tri (C6-C12) arylsilyl and is, for example, independently hydrogen; Phenyl unsubstituted or substituted with cyano, naphthyl or triphenylsilyl; Naphthyl substituted or unsubstituted with phenyl; Biphenyl substituted or unsubstituted with naphthyl; Terphenyl; Phenanthrenyl; Fluorenyl substituted by methyl or phenyl; Fluoranthenyl; Or perylenyl.

Said heteroaryl comprises at least one heteroatom selected from B, N, O, S, Si and P, preferably comprising at least one heteroatom selected from N, O and S.

In the above formula (2), L ₁ is a single bond or a substituted or unsubstituted (C6-C30) arylene, preferably a single bond or a substituted or unsubstituted (C6-C12) Is a single bond or (C6-C12) arylene substituted or unsubstituted with a tri (C6-C10) arylsilyl, for example, a single bond, phenylene, naphthylene substituted or unsubstituted with triphenylsilyl, Biphenylene.

In the formula (2), L ₁ may be represented by one of the following formulas (7) to (19).

In the above formulas (7) to (19)

Xi to Xp are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2- Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri (C6-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted mono- or Di- (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is selected from nitrogen, oxygen, and sulfur (C6-C15) aryl, substituted or unsubstituted (10-20 membered) heteroaryl, or substituted or unsubstituted heteroaryl, each optionally substituted with one or more heteroatoms and is preferably independently selected from the group consisting of hydrogen, cyano, substituted or unsubstituted (C6-C60) arylsilyl, more preferably each independently hydrogen or unsubstituted tri (C6-C10) arylsilyl, for example, each independently hydrogen or unsubstituted triphenylsilyl .

In Formula 2, Ar ₁ is substituted or unsubstituted (3-30 membered) heteroaryl, preferably substituted or unsubstituted nitrogen (5-11 member) heteroaryl, more preferably cyano, (C6-C18) aryl unsubstituted or substituted with (C1-C6) alkyl or tri (C6-C12) arylsilyl; And (6-15 membered heteroaryl) substituted or unsubstituted nitrogen-containing (5-11 membered) heteroaryl.

Ar ₁ is a monocyclic heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, Benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl and phenanthridinyl And preferably fused ring heteroaryl selected from the group consisting of pyridyl, pyrimidinyl, pyridyl, quinolyl, isoquinoline, quinazolinyl, naphthyridinyl or quinoxalinyl.

Wherein R ₁₁ to R ₁₈ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) alkoxy, substituted or unsubstituted tri (C1- (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, ) Alkyl (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, the carbon atom of the alicyclic or aromatic ring being formed may be a substituted or unsubstituted monocyclic or polycyclic Lt; / RTI > or more heteroatoms; (C6-C12) aryl, substituted or unsubstituted (10-20 membered) heteroaryl, or substituted or unsubstituted tri (C6-C12) aryl Silyl; To form a substituted or unsubstituted monocyclic or polycyclic aromatic ring (C6-C20), more preferably each independently hydrogen; Cyano; (C6-C15) aryl unsubstituted or substituted with (C6-C10) arylsilyl; (10-20 membered) heteroaryl substituted or unsubstituted with cyano or (C6-C12) aryl; Or unsubstituted tri (C6-C10) arylsilyl; Substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, .

The term "(C1-C30) alkyl" as used herein means straight chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, preferably having 1 to 20 carbon atoms, and having 1 to 10 More preferable. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. The term " (C2-C30) alkenyl " as used herein means straight chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 desirable. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, the term "(C2-C30) alkynyl" means straight chain or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 desirable. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. The term " (C3-C30) cycloalkyl " used herein means a single ring or polycyclic hydrocarbon having 3 to 30 ring skeletal 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. The term " (3-7 member) heterocycloalkyl " as used herein refers to a heterocycloalkyl group having 3 to 7, preferably 5 to 7, ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, Means a cycloalkyl containing one or more heteroatoms selected from atoms, preferably O, S and N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. The term "(C6-C30) aryl (phenylene)" as used herein means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20 . Examples of such aryls include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, , Fluoranthenyl, and the like. As used herein, the term "(3-30) heteroaryl (phenylene)" means an aryl group having 3 to 30 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P it means. Here, it is preferable that the number of the atoms of the ring skeleton is 10 to 30. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) in the present invention also includes a form in which one or more heteroaryl groups or aryl groups are linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, the term "nitrogen-containing (5-30 membered) heteroaryl (phenylene)" means an aryl group having 5 to 30 ring skeletal atoms and containing one or more heteroatoms N. Here, it is preferable that the number of the atoms of the ring skeleton is 10 to 30. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the nitrogen-containing heteroaryl (phenylene) in the present application also includes a form in which one or more heteroaryl groups or aryl groups are linked to a heteroaryl group by a single bond. Examples of the nitrogen-containing heteroaryl include monocyclic heteroaryls such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, , Fused ring systems such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, Heteroaryl, and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Also, in the phrase "substituted or unsubstituted" described herein, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. The term substituted alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted alkoxy, substituted aryl (phenylene), substituted heteroaryl (phenylene), substituted trialkylsilyl, substituted triaryl Substituted mono-or di-alkylamino, substituted mono-or di-alkylamino, or a substituted mono- or poly-alicyclic or aromatic ring Each substituent is independently selected from the group consisting of deuterium; halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-30 membered) heteroaryl, unsubstituted or substituted with (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with (C3-C30) 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) aryl (C1-C30) alkyl and (C1-C30) alkyl (C6-C30) aryl, and preferably each independently represents ; (5-15 membered) heteroaryl; (C6-C20) aryl unsubstituted or substituted with cyano, (C6-C12) aryl or tri (C6-C12) arylsilyl; Tri (C6-C12) arylsilyl; And (C1-C6) alkyl (C6-C12) aryl.

The first host compound represented by Formula 1 is selected from the group consisting of the following compounds, but is not limited thereto.

The second host compound represented by Formula 2 is selected from the group consisting of the following compounds, but is not limited thereto.

An organic electroluminescent device according to the present invention includes: a cathode; cathode; And at least one organic material layer interposed between the anode and the cathode, wherein the organic material layer includes at least one light emitting layer, the light emitting layer includes a host and a phosphorescent dopant, and the host comprises a plurality of host compounds At least a first host compound of the plurality of host compounds is represented by the formula (1), and a second host compound is represented by the formula (2).

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 in the light emitting layer is preferably less than 20% by weight.

The organic material layer may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron affinity layer, an electron buffer layer, an interlayer, a hole blocking layer, and an electron blocking layer .

In the organic electroluminescent device of the present invention, the weight ratio of the first host compound to the second host compound ranges from 1:99 to 99: 1.

The dopant included in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) And more preferably an ortho-metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and still more preferably an orthometallated iridium complex compound.

The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following Chemical Formulas (101) to (103).

In the above formulas (101) to (103)

La is selected from the following structures;

R ₁₀₀ is hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl;

R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, cyano, substituted or unsubstituted (C 1 -C 30) alkoxy, Substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) cycloalkyl; R ₁₀₆ to R ₁₀₉ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, Or dibenzofuran which is substituted or unsubstituted with alkyl is possible; R ₁₂₀ to R ₁₂₃ may be connected to each other to form a substituted or unsubstituted fused ring, for example, quinoline substituted or unsubstituted with alkyl or aryl;

R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; R ₁₂₄ to R ₁₂₇ may be connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, or alkyl Substituted or unsubstituted dibenzofuran can be formed;

R ₂₀₁ to R ₂₁₁ each independently represents hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, or substituted or unsubstituted And R < ₂₁₁ &_gt; to R < ₂₁₁ &_gt; may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring. For example, fluorine, substituted or unsubstituted alkyl, Dibenzothiophene, or dibenzofuran substituted or unsubstituted with alkyl is possible;

r and s are each independently an integer of 1 to 3; When r or s each is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other;

and e is an integer of 1 to 3.

Specific examples of the phosphorescent dopant material are as follows.

The organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in the organic material layer.

In the organic electroluminescent device of the present invention, the organic material layer may include one or more metals selected from the group consisting of Group 1, Group 2, and 4 period transition metals, 5 period transition metals, lanthanide series metals and d- , Or one or more complex compounds comprising such metals.

In the organic electroluminescent device of the present invention, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer "Quot;). Concretely, it is preferable to arrange a layer of a chalcogenide (including an oxide) of silicon and aluminum on the surface of the anode on the side of the light emitting medium layer and a metal halide layer or metal oxide layer on the surface of the cathode on the side of the light emitting medium layer. The driving layer of the organic electroluminescent device can be stabilized by the surface layer. Preferable examples of the chalcogenide include SiO _x (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON and SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

A hole injecting layer, a hole transporting layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be formed of a plurality of layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each layer may use two compounds at the same time. A plurality of layers may also be used for the hole transporting layer or the electron blocking layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be formed of a plurality of layers for the purpose of controlling electron injection and improving interfacial characteristics between the light emitting layer and the electron injection layer, and each layer may use two compounds at the same time. A plurality of layers may also be used as the hole blocking layer or the electron transporting layer, and a plurality of compounds may be used for each layer.

In the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transport compound and the oxidative dopant, on at least one surface of the pair of electrodes . In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, an organic electroluminescent device emitting light of white color having two or more light emitting layers can be manufactured by using a reducing dopant layer as a charge generation layer.

The formation of the respective layers of the organic electroluminescent device of the present invention may be performed by a dry film forming method such as vacuum deposition, sputtering, plasma or ion plating, or by a method such as ink jet printing, nozzle printing, slot coating ), A spin coating method, a dip coating method, and a flow coating method.

In the case of the wet film-forming method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane to form a thin film, in which the material forming each layer is dissolved or dispersed And it may be any thing which does not have a problem in the formation of the tabernacle.

In addition, the first host compound and the second host compound of the present invention can be deposited by a co-deposition or mixed deposition process.

The co-deposition is a method in which two or more isomeric materials are placed in respective individual crucible sources, and current is applied to both cells simultaneously to evaporate the materials to be mixed and deposited. The mixed deposition is a method in which two or more isomer materials After mixing with a crucible source, a current is applied to one cell to evaporate the material and mix it.

Further, it is possible to manufacture a display device or a lighting device using the organic electroluminescent device of the present invention.

Hereinafter, the luminescent characteristics of a device including the host compound of the present invention will be described for the purpose of a detailed understanding of the present invention.

[device Manufacturing example  1-1] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

OLED devices were prepared using the organic electroluminescent compound of the present invention. First, a transparent electrode ITO thin film (10? /?) On a glass substrate for OLED (manufactured by Geomatex) was subjected to ultrasonic cleaning using acetone, ethanol and distilled water sequentially, and then stored in isopropanol before use. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N ⁴ , N ^{4 '} -diphenyl-N ⁴ , N ^4' -bis (9-phenyl-9H- (HI-1) was added to the chamber, and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. Then, a current was applied to the cell And evaporated to deposit a first hole injection layer having a thickness of 80 nm on the ITO substrate. Subsequently, 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was placed in another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate the first hole A second hole injection layer having a thickness of 3 nm was deposited on the injection layer. Then, another cell in a vacuum deposition equipment was charged with N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9- Yl) phenyl) -9H-fluorene-2-amine (compound HT-1) was charged and the cell was evaporated by applying a current to deposit a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Then, another cell in a vacuum deposition equipment was charged with N - ([1,1'-biphenyl] -4-yl) -N- (4- (9- (dibenzo [ 9H-fluorene-9-yl) phenyl) - [1,1'-biphenyl] -4-amine (compound HT-2) was added and the cell was evaporated by applying a current, Thick second hole transporting layer. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. Compounds K-1 and H2-125 were added as hosts to two cells in a vacuum deposition apparatus, and compound D-1 as a dopant in another cell, followed by evaporation of the two host materials at the same rate of 1: 1 At the same time, the dopant material was evaporated at a different rate to form a light emitting layer having a thickness of 40 nm on the hole transport layer by doping the dopant in an amount of 15 wt% with respect to the total amount of the host and the dopant. Then, in another two cells, 2,4-bis (9,9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3,5-triazine ET-1) and lithium quinolate (Compound EI-1) were evaporated at a rate of 4: 6 to deposit an electron transport layer having a thickness of 35 nm on the light emitting layer. Then, lithium quinolate (Compound EI-1) was deposited to a thickness of 2 nm as an electron injecting layer, and an Al cathode was deposited to a thickness of 80 nm using another vacuum vapor deposition apparatus to prepare an OLED device.

[ Comparative Example  RTI ID = 0.0 > 1-1] < / RTI > OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1-1, except that only the first host compound K-1 was used as the host of the light emitting layer.

[ Comparative Example  Lt; RTI ID = 0.0 > 1-2] < / RTI > OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1-1, except that only the second host compound H2-125 was used as the host of the light emitting layer.

The driving voltage, the luminous efficiency, the CIE color coordinates, and the luminance constant based on 1,000 nits of the organic EL device manufactured in the Device Manufacturing Example 1-1 and Comparative Examples 1-1 and 1-2 were 100% to 90% % Is shown in Table 1. < tb >< TABLE >

[Table 1]

[device Manufacturing example  2-1] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 1-1 except that D-25 was used as a dopant.

[ Comparative Example  2-1] < / RTI > OLED  Device Manufacturing

An OLED device was manufactured in the same manner as in the Device Production Example 2-1 except that only the second host compound H2-125 was used as the host of the light emitting layer.

The driving voltage, luminous efficiency, CIE chromaticity coordinates, and lifetime time of the organic electroluminescent device manufactured in the above-described Device Manufacturing Example 2-1 and Comparative Example 2-1 were decreased from 100% to 97% Are shown in Table 2 below.

[Table 2]

[device Manufacturing example  3-1] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

An OLED device was fabricated in the same manner as in Production Example 1-1 except that D-136 was used as a dopant.

[ Comparative Example  3-1] < / RTI > OLED  Device Manufacturing

OLED devices were fabricated in the same manner as in the Device Production Example 3-1 except that only the second host compound H2-125 was used as the host of the light emitting layer.

The driving voltage, the luminous efficiency, the CIE chromaticity coordinates, and the lifetime of the organic electroluminescent device manufactured from the device preparation example 3-1 and the comparative example 3-1 decreased from 100% to 95% Are shown in Table 3 below.

[Table 3]

[device Manufacturing example  4-1 to 4-4] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

OLED devices were prepared using the organic electroluminescent compound of the present invention. First, a transparent electrode ITO thin film (10? /?) Obtained from a glass for OLED (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 was mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI-2 was added to the cell in the vacuum deposition apparatus. After evacuation was performed until the degree of vacuum in the chamber reached 10 ^-6 torr, And evaporated to deposit a hole injection layer having a thickness of 5 nm on the ITO substrate. Next, compound NPB was placed in another cell in the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the first hole transporting layer to deposit a first hole transporting layer having a thickness of 95 nm on the hole injecting layer. Then, a compound HT-2 was added to another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate the second hole transport layer to deposit a second hole transport layer having a thickness of 20 nm. After the hole injecting layer and the hole transporting layer were formed, a light emitting layer was deposited thereon as follows. The first host compound and the second host compound of Production Examples 4-1 to 4-4 shown in Table 4 below were put into two cells in the vacuum deposition equipment, respectively, and the other cell contained Compound D-125 as a dopant Then, the two host materials were evaporated at the same rate of 1: 1, and at the same time, the dopant material was evaporated at a different rate so that dopant was doped in an amount of 12% by weight based on the total amount of host and dopant, A light emitting layer with a thickness of 30 nm was deposited. Then, compound ET-2 was deposited as an electron transport layer with a thickness of 35 nm on the light-emitting layer in two other cells. Subsequently, compound EI-1 was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 80 nm using another vacuum vapor deposition apparatus to produce an OLED device.

[ Comparative Example  4-1 & 4-2] containing only the second host compound as the host OLED  Device Manufacturing

OLED devices were manufactured in the same manner as in the Device Production Examples 4-1 to 4-4 except that the host of Comparative Examples 4-1 and 4-2 described in Table 4 was used as the host of the light emitting layer.

The device produced in Example 4-1 to 4-4, and Comparative Examples 4-1 and 4-2, the driving voltage of 10 mA / cm ² based on the organic electroluminescent device prepared in luminance efficiency, CIE color coordinate and luminance 10,000 nits reference The life time at which the constant current falls from 100% to 97% is shown in Table 4 below.

[Table 4]

[device Manufacturing example  5-1 and 5-2] The first host compound and the second host compound according to the present invention Notarized good OLED  Device Manufacturing

A second hole injection layer was deposited to a thickness of 5 nm and a second hole transport layer was deposited to a thickness of 60 nm to form a compound HT-3, and the first host of Device Production Examples 5-1 and 5-2 And D-96 as a dopant were doped in an amount of 3% by weight, and the electron transport layer was vapor-deposited at a rate of 1: 1 at a thickness of 30 nm. To prepare an OLED device.

[ Comparative Example  RTI ID = 0.0 > 5-1] < / RTI > OLED  Device Manufacturing

OLED devices were manufactured in the same manner as in the Device Production Example 5-1 except that only the second host compound H2-41 was used as the host of the light emitting layer.

The driving voltage, luminous efficiency and CIE color coordinates of the organic EL device manufactured in the above-described Device Production Examples 5-1 and 5-2 and Comparative Example 5-1 were 1,000 to 98 ng at a constant current of 5,000 nits, % Is shown in Table 5. < tb >< TABLE >

[Table 5]

The present invention relates to a plurality of kinds of host materials and an organic electroluminescent device including the same. According to the present invention, it is possible to manufacture an organic electroluminescent device in which the current efficiency and the power efficiency are improved and the driving life is remarkably improved by using a plurality of kinds of hosts as compared with the conventional device using one kind of host.

Claims (7)

And at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes a host and a phosphorescent dopant, wherein the host comprises a plurality of host compounds, and at least a first host compound Is represented by the following formula (1), and the second host compound is represented by the following formula (2).
[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,
Ar < ₁ > is a substituted or unsubstituted (3-30 membered) heteroaryl, provided that the pyrimidine
Occation

, And carbazole are excluded;
L ₁ is a single bond, or a substituted or unsubstituted (C 6 -C 30) arylene;
R ₁ to R ₈ and R ₁₁ to R ₁₈ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) alkoxy, substituted or unsubstituted tri (C1-C30) (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6- C30) alkyl (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring which is connected to each other to form a substituted or unsubstituted monocyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is a Lt; / RTI > or more heteroatoms;
Wherein said heteroaryl comprises one or more heteroatoms selected from B, N, O, S, Si and P; The method according to claim 1,
Wherein R ₁ to R ₈ in Formula 1 are each independently selected from the following structures.

Wherein L is a substituted or unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (5-20 membered) heteroarylene;
n is an integer from 0 to 2;
R ₂₁ to R ₂₅ and R ₃₁ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring which is connected to each other to form a substituted or unsubstituted monocyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is a Lt; / RTI > or more heteroatoms;
Wherein said heteroaryl comprises one or more heteroatoms selected from B, N, O, S, Si and P; The method according to claim 1,
Wherein L < ₁ > in the above formula (2) is represented by any one of the following formulas (7) to (19).

In the above formulas (7) to (19)
Xi to Xp are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2- Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted tri (C6-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted mono- or Di- (C6-C30) arylamino; (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring linked to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and the carbon atom of the alicyclic or aromatic ring formed is selected from nitrogen, oxygen, and sulfur May be replaced by one or more heteroatoms. The method according to claim 1,
Ar ₁ in Formula 2 is a monocyclic heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl Or a group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl and phenanthridinyl Lt; RTI ID = 0.0 > heteroaryl < / RTI > The method according to claim 1,
R ₁₁ to R ₁₈ in Formula 2 are each independently substituted with (C6-C15) aryl, cyano, or (C6-C12) aryl substituted or unsubstituted with hydrogen, cyano, tri Or unsubstituted (10-20 membered) heteroaryl, or unsubstituted tri (C6-C10) arylsilyl; Substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, substituted or unsubstituted benzenes, To form an organic electroluminescent device. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 2 is selected from the following compounds.