Multicomponent host material and organic electroluminescent device containing the same

Abstract

To provide an organic electroluminescent device with high efficiency and long lifespan. [Solution] An organic electroluminescent 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, the host comprising a multicomponent host compound, at least the first host compound of the multicomponent host compound being a specific bicarbazole derivative containing an aryl group, and the second host compound being a specific carbazole derivative containing a nitrogen-containing heteroaryl group.

Description

[Technical Field]

[0001] The present invention relates to a multi-component host material and an organic electroluminescent device containing the same. [Background technology]

[0002] Electroluminescent (EL) devices are self-emissive devices that offer advantages such as a wider visual field, higher contrast ratio, and faster reaction time. Organic EL devices were first developed by Eastman Kodak using aromatic diamine small molecules and aluminum complexes as materials to form the emissive layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] Organic light-emitting diode (OLED) devices convert electrical energy into light by injecting electric charge into an organic light-emitting material, and generally comprise an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of an OLED device may consist of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emissive layer (EML) (containing host and dopant materials), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). The materials used within the organic layers can be classified according to their function into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In an OLED device, holes from the anode and electrons from the cathode are injected into the emissive layer by electric charge injection, and high-energy excitons are generated by the recombination of holes and electrons. This energy moves the organic light-emitting compound to an excited state, and when the organic light-emitting compound returns from the excited state to the ground state, it emits light that changes in energy.

[0004] The most important factor determining the luminous efficiency within an organic EL device is the luminescent material. The luminescent material must possess the following characteristics: high quantum efficiency, high electron and hole mobility, the ability to form uniform layers, and stability. Luminescent materials are classified by emission color into blue, green, and red luminescent materials, further including yellow or orange luminescent materials. Furthermore, luminescent materials are classified into host materials and dopant materials in terms of functionality. In recent years, there has been an urgent need to develop organic EL devices with high effectiveness and long operating life. In particular, considering the EL properties required for medium and large OLED panels, the development of luminescent materials significantly superior to conventional luminescent materials is urgently needed. For this purpose, the host material should preferably have high purity and a suitable molecular weight for deposition under vacuum as a solid-state solvent and energy transfer substance. Furthermore, the host material needs to have high glass transition temperature and thermal decomposition temperature to ensure thermal stability, high electrochemical stability for long life, the ability to easily form amorphous thin films, good adhesion to adjacent layers, and no interlayer migration.

[0005] Mixed systems of dopant / host materials can be used as luminescent materials to improve color purity, luminescence efficiency, and stability. Generally, devices with the best EL properties have a luminescent layer in which the dopant is doped onto the host. Since the host material significantly affects the efficiency and performance of the luminescent device, the selection of the host material is important when a dopant / host material system is used.

[0006] International Publication No. 2013 / 168688 A1, Japanese Patent No. 3139321, Korean Patent No. 10-1170666, Korean Patent Application Publication No. 10-2012-0013173, and International Publication No. 2013 / 112557 A1 disclose organic EL devices including dopant / host material systems. The above documents use one host component having a carbazole-carbazole skeleton, i.e., excluding hosts having a cabazole skeleton from the second and third hosts.

[0007] The inventors have found that an organic EL device using a multi-component host compound having a specific bicarbazole derivative containing an aryl group and a specific carbazole derivative containing a nitrogen-containing heteroaryl group has higher efficiency and longer lifespan compared to a device using a single-component host compound in the light-emitting layer. [Overview of the Initiative]

[0008] The objective of the present invention is to provide an organic EL device with high efficiency and long lifespan. [Means for solving the problem]

[0009] The above objective can be achieved by an organic electroluminescent device comprising at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, the host comprising a multicomponent host compound, the first of which is a specific bicarbazole derivative containing an aryl group and represented by the following formula 1, and the second host compound comprising a specific carbazole derivative containing a nitrogen-containing heteroaryl group and represented by the following formula 2.

[0010] [ka]

[0011] During the ceremony, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30) aryl group. X1~X 16Each of these independently represents hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C2-C30) alkynyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, substituted or unsubstituted 3-30 membered heteroaryl group, substituted or unsubstituted tri(C1-C30) alkylsilyl group, substituted or unsubstituted Represents a tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or unsubstituted mono or di(C6-C30)arylamino group, or forms a substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, where carbon atoms may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur, linked between adjacent substituents. Ma represents a substituted or unsubstituted nitrogen-containing 5-30 membered heteroaryl group. La represents a single bond or a substituted or unsubstituted (C6-C30) arylene group, and Xa to Xh independently represent hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C2-C30) alkynyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, substituted or unsubstituted 3-30 membered heteroaryl group, substituted or unsubstituted tri(C1-C30) alkylsilyl group, substituted or unsubstituted Representing a substituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or unsubstituted mono or di(C6-C30)arylamino group, or forming a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30)alicyclic or aromatic ring, in which a ring of carbon atoms may be substituted by at least one heteroatom selected from nitrogen, oxygen, and sulfur, linked between adjacent substituents. The condensed aromatic ring or the condensed aromatic heterocyclic ring is selected from the group consisting of benzene, indole, indene, benzofuran, and benzothiophene, and may be further substituted with a (C1-C10) alkyl group or a (C6-C15) aryl group. The heteroaryl group contains at least one heteroatom selected from B, N, O, S, P(=O), Si, and P.

Effects of the Invention

[0012] According to the present invention, an organic EL device having high efficiency and long life is provided, and it is possible to produce a display device or a lighting device by using the organic EL device.

Modes for Carrying Out the Invention

[0013] Hereinafter, the present invention will be described in detail. However, the following description is for the purpose of explaining the present invention and is not intended to limit the scope of the present invention in any way.

[0014] The compound of Formula 1 is represented by the following Formula 3, 4, 5, or 6.

[0015]

Chemical Formula

[0016] In the formula, A1, A2, and X1 to X 16 are as defined in Formula 1. In Formula 1, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group, preferably a substituted or unsubstituted (C6-C18)aryl group, more preferably an unsubstituted (C6-C18)aryl group substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group, or a tri(C6-C12)arylsilyl group, and even more preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, naphthacenyl, or fluoranthenyl.

[0017] In formula 1, X1~X 16 Each of these independently represents hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C2-C30) alkynyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, substituted or unsubstituted 3-30 membered heteroaryl group, substituted or unsubstituted tri(C1-C30)alkylsilyl group, substituted or unsubstituted tri(C6-C30)arylsilyl group, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or substituted or unsubstituted mono or di(C6-C30)aryl The group represents a ruamino group, preferably hydrogen, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted tri(C6-C12)arylsilyl group, or a substituted or unsubstituted 3-15 membered heteroaryl group, more preferably hydrogen, a substituted or unsubstituted (C6-C18)aryl group, an unsubstituted triphenylsilyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, in which a ring of carbon atoms may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur by linking between adjacent substituents.

[0018] The compound of formula 2 is represented by formula 7, 8, or 9 below,

[0019] [ka]

[0020] During the ceremony, V and W are independently single bonds, NR 15 , CR 16 R 17 NR represents S or O, however, both V and W can also represent a single bond. 15 On the condition that it does not represent, A2 represents a substituted or unsubstituted (C6-C30)aryl group, which may be bonded to Xn or Xo. L3 and L4 each independently represent a single bond or a substituted or unsubstituted (C6-C60) arylene group. Xi is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C2-C30) alkynyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, substituted or unsubstituted 3-30 membered heteroaryl group, substituted or unsubstituted tri(C1-C30) alkylsilyl group, substituted or unsubstituted tri( Representing a C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or unsubstituted mono or di(C6-C30)arylamino group, or forming a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30)alicyclic or aromatic ring, in which a ring of carbon atoms may be substituted by at least one heteroatom selected from nitrogen, oxygen, and sulfur, linked between adjacent substituents. Xj to Xz are each independently hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60) aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, -NR5R6, or -SiR7R8R9, or are linked between adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30) alicyclic ring or aromatic ring which may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur and having carbon atom(s), Ma, La, Xa, Xb, and Xe to Xh are as defined in Formula 2, R5 to R9 are each independently hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60) aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group, preferably hydrogen, or a substituted or unsubstituted (C6-C25) aryl group, more preferably hydrogen, or an unsubstituted (C6-C18) aryl group, particularly hydrogen, an unsubstituted phenyl group, a biphenyl group, or a fluorenyl group, or are linked between adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30) alicyclic ring or aromatic ring which may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur and having carbon atom(s), R 16 and R 17Each of these independently represents hydrogen, deuterium, halogen, cyano group, carboxyl group, nitro group, hydroxyl group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C3-C30) cycloalkenyl group, substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, or substituted or unsubstituted 3- to 30-membered heteroaryl group. R 15 This represents hydrogen, deuterium, halogen, cyano group, carboxyl group, nitro group, hydroxyl group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C3-C30) cycloalkenyl group, substituted or unsubstituted 3-7 member heterocycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, or substituted or unsubstituted 3-30 member heteroaryl group, preferably a substituted or unsubstituted (C6-C30) aryl group, more preferably a substituted or unsubstituted phenyl group, unsubstituted biphenyl group, unsubstituted naphthyl group, or substituted fluorenyl group.

[0021] In formula 2, La represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond, or a substituted or unsubstituted (C6-C12) arylene group, more preferably a single bond, unsubstituted or (C6-C12) arylene group substituted with a tri(C6-C10) arylsilyl group or a (C6-C12) aryl group.

[0022] Furthermore, La represents a single bond, or is represented by one of the following equations 10-19:

[0023] [ka]

[0024] During the ceremony, Xi~Xp can each independently be hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C2-C30) alkenyl group, substituted or unsubstituted (C2-C30) alkynyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C60) aryl group, substituted or unsubstituted 3-30 membered heteroaryl group, substituted or unsubstituted tri(C1-C30) alkylsilyl group, substituted or unsubstituted tri(C6-C30) arylsilyl group, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or substituted or unsubstituted mono or di(C6-C30) arylamino group, preferably ≤ represents hydrogen, a cyano group, a substituted or unsubstituted (C6-C15)aryl group, a substituted or unsubstituted 10-20 member heteroaryl group, or a substituted or unsubstituted tri(C6-C10)arylsilyl group, more preferably a (C6-C15)aryl group substituted with hydrogen, a cyano group, an unsubstituted or tri(C6-C10)arylsilyl group, or a 10-20 member heteroaryl group substituted with an unsubstituted or (C6-C15)aryl group, or a substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring in which a ring of carbon atoms may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur by linking between adjacent substituents.

[0025] In Formula 2, Ma represents a nitrogen-containing 6-10 member heteroaryl group substituted with a substituent(s) selected from the group consisting of a substituted or unsubstituted nitrogen-containing 5-11 member heteroaryl group, preferably a substituted or unsubstituted nitrogen-containing 6-10 member heteroaryl group, more preferably an unsubstituted (C6-C18) aryl group, a (C6-C12) aryl group substituted with a cyano group, a (C1-C6) alkyl group substituted with a (C6-C12) alkyl group, a (C6-C12) aryl group substituted with a tri(C6-C12) arylsilyl group, and a 6-15 member heteroaryl group.

[0026] Furthermore, Ma represents a monocyclic heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, or a fused ring heteroaryl group selected from the group consisting of benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthilidinyl, quinoxalinyl, carbazolyl, phenantridinyl, or more, preferably triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthilidinyl, or quinoxalinyl.

[0027] In this specification, "(C1-C30) alkyl(ene)" is intended to mean a linear or branched alkyl(ene) having 1 to 30 carbon atoms (where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10), and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like.

[0028] "(C2-C30) alkenyl" is intended to be a linear or branched alkenyl having 2 to 30 carbon atoms (where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10), and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbuta-2-enyl, etc. "(C2-C30) alkynyl" is a linear or branched alkynyl having 2 to 30 carbon atoms (where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10), and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpenta-2-inyl, etc. "(C3-C30) cycloalkyl" refers to monocyclic or polycyclic hydrocarbons having 3 to 30 carbon atoms (where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7), and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "3-7 membered heterocycloalkyl" refers to cycloalkyls having at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si, and P, preferably O, S, and N, and 3 to 7, preferably 5 to 7 cyclic skeleton atoms, and includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. "(C6-C30)aryl(ene)" is a monocyclic or fused ring derived from aromatic hydrocarbons having 6 to 30 carbon atoms (where the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15), and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, and the like.A "3-30 membered heteroaryl(ene)" is an aryl group having at least one, preferably 1-4, heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si, and P, and 3-30 ring skeleton atoms, and is a monocyclic ring or a fused ring fused with at least one benzene ring, preferably having 3-20, more preferably 3-15 ring skeleton atoms, and may be partially saturated, and may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via single bonds (multiple single bonds are possible), such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxy This includes monocyclic heteroaryl groups such as sazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridadinyl, and condensed heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, sinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenantridinyl, and benzodioxolyl. A "nitrogen-containing 5-30 membered heteroaryl(ene) group" is an aryl(ene) group having at least one heteroatom N and 5-30 ring skeleton atoms. 5 to 20 ring skeleton atoms and 1 to 4 heteroatoms are preferred, and 5 to 15 ring skeleton atoms are more preferred.This includes monocyclic rings or fused rings formed by condensing at least one benzene ring, which may be partially saturated and may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via single bonds (or multiple single bonds), and includes monocyclic heteroaryls such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridadinyl, and fused heteroaryls such as benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, sinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, and phenantridinyl. "Halogen" includes F, Cl, Br, and I.

[0029] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is substituted with another atom or group, i.e., a substituent. A substituted alkyl(ene) group, substituted alkenyl group, substituted alkynyl group, substituted cycloalkyl group, substituted aryl(ene) group, substituted heteroaryl(ene) group, substituted trialkylsilyl group, substituted triarylsilyl group, substituted dialkylarylsilyl group, substituted mono or diarylamino group, or a substituted monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring substituent is independently a deuterium, halogen, cyano group, carboxyl group, nitro group, hydroxyl group, (C 1-C30) alkyl groups, halo(C1-C30) alkyl groups, (C2-C30) alkenyl groups, (C2-C30) alkynyl groups, (C1-C30) alkoxy groups, (C1-C30) alkylthio groups, (C3-C30) cycloalkyl groups, (C3-C30) cycloalkenyl groups, 3-7 member heterocycloalkyl groups, (C6-C30) aryloxy groups, (C6-C30) arylthio groups, unsubstituted or substituted 3-30 member heteroaryl groups, unsubstituted or shea (C6-C30)aryl groups substituted with a no group, a 3-30 member heteroaryl group, or a tri(C6-C30)arylsilyl group, tri(C1-C30)alkylsilyl group, tri(C6-C30)arylsilyl group, di(C1-C30)alkyl(C6-C30)arylsilyl group, (C1-C30)alkyldi(C6-C30)arylsilyl group, amino group, mono or di(C1-C30)alkylamino group, mono or di(C6-C30)arylamino group, (C1-C30) It is at least one selected from the group consisting of aryl(C6-C30)arylamino group, (C1-C30)alkylcarbonyl group, (C1-C30)alkoxycarbonyl group, (C6-C30)arylcarbonyl group, di(C6-C30)arylboronyl group, di(C1-C30)alkylboronyl group, (C1-C30)alkyl(C6-C30)arylboronyl group, (C6-C30)aryl(C1-C30)alkyl group, and (C1-C30)alkyl(C6-C30)aryl group.Preferably, each substituent is independently selected from the group consisting of (C1-C6)alkyl groups, 5-15 member heteroaryl groups, unsubstituted (C6-C18)aryl groups substituted with a cyano group or a tri(C6-C12)arylsilyl group, tri(C6-C12)arylsilyl groups, and (C1-C6)alkyl(C6-C12)aryl groups.

[0030] The compound of formula 1 as the first host compound may be selected from, but is not limited to, the group consisting of the following compounds.

[0031] [ka]

[0032] [ka]

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] The compound of formula 2, as the second host compound, may be selected from, but is not limited to, the group consisting of the following compounds.

[0037] [ka]

[0038] [ka]

[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049] The organic EL device according to the present invention may comprise an anode, a cathode, and at least one organic layer between the two electrodes, the organic layer comprising an emissive layer, the emissive layer comprising a host and a phosphorescent dopant, the host comprising a multicomponent host compound, at least one of the multicomponent host compounds being represented by formula 1, which is a specific bicarbazole derivative containing an aryl group, and the second host compound being represented by formula 2, which is a specific carbazole derivative containing a nitrogen-containing heteroaryl group.

[0050] The light-emitting layer refers to a layer that emits light, and may be a single layer or a multilayer consisting of two or more layers. The doping concentration of the dopant compound to the host compound in the light-emitting layer is preferably less than 20% by weight.

[0051] The dopant contained in the organic EL device of the present invention is preferably one or more phosphorescent dopants. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but can be preferably selected from a complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably from an orthometalated complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably from an orthometalated iridium complex compound.

[0052] The phosphorescent dopant may be selected from the group consisting of compounds represented by the following formulas 101-103.

[0053] [ka]

[0054] L is selected from the following structures:

[0055] [ka]

[0056] R 100R represents hydrogen or a substituted or unsubstituted (C1-C30) alkyl group. 101 ~R 109 and R 111 ~R 123 Each of these independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (multiple) (C1-C30) alkyl group, cyano group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted (C6-C30) aryl group, or substituted or unsubstituted (C3-C30) cycloalkyl group, R 120 ~R 123 It links with adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30) alicyclic or aromatic ring, such as quinoline, R 124 ~R 127 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, or substituted or unsubstituted (C6-C30) aryl group, R 124 ~R 127 When is an aryl group, they link with adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30) alicyclic or aromatic ring, or heteroatomic ring, such as fluorene, dibenzothiophene, or dibenzofuran, R 201 ~R 211 Each of these independently represents hydrogen, deuterium, halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group, R 208 ~R 211 R may be linked with adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic, (C3-C30) alicyclic or aromatic ring, or heteroatomic ring, such as fluorene, dibenzothiophene, or dibenzofuran, where r and s each independently represent an integer from 1 to 3, and when r or s is an integer of 2 or more, R 100 Each of these can be the same or different, and e represents an integer from 1 to 3.

[0057] Phosphorescent dopant materials include the following:

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] The organic EL device of the present invention may further contain in the organic layer at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds.

[0062] In the organic EL device of the present invention, the organic layer may further include at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic d transition elements, or at least one complex compound containing such metal.

[0063] Preferably, 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 the "surface layer") may be disposed on the inner surface(s) of one or both electrodes(s). Specifically, it is preferable that a silicon or aluminum chalcogenide (including oxide) layer is disposed on the anode surface of the light-emitting medium layer, and a metal halide layer or metal oxide layer is disposed on the cathode surface of the electroluminescent medium layer. This surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X(1≦X≦1.5), includes SiON, SiAlON, etc., metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0064] A hole injection layer, hole transport layer, electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, each of which uses two compounds simultaneously. The hole transport layer or electron blocking layer may also be multilayered.

[0065] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, with each of these layers simultaneously using two compounds. The hole blocking layer or electron transport layer may also be multilayered, with each of these layers potentially using a multicomponent compound.

[0066] Preferably, in the organic electroluminescent device of the present invention, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant, can be arranged on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and therefore it becomes easier to inject electrons and transport them from the mixed region to the light-emitting medium. Furthermore, the hole transport compound is oxidized to cations, and therefore it becomes easier to inject holes and transport them from the mixed region to the light-emitting medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. To prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light, a reductive dopant layer can be used as a charge-generating layer.

[0067] To form each layer constituting the organic electroluminescent device of the present invention, dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, or wet film formation methods such as spin coating, dip coating, and flow coating may be used. When forming layers using the first and second hosts according to the present invention, co-deposition or mixed deposition may be used.

[0068] When using the wet film formation method, thin films are formed by dissolving or dispersing the materials constituting each layer in a suitable solvent, such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent is not particularly limited, as long as the materials constituting each layer are soluble or dispersible in the solvent and do not cause problems during layer formation.

[0069] Furthermore, by using the organic EL device of the present invention, display devices or optical devices can be produced.

[0070] Hereafter, the method for preparing devices using the host compound and dopant compound of the present invention will be described in detail with reference to the following examples.

[0071] Device Example 1-1: Generation of an OLED device by simultaneously depositing a first host compound and a second host compound according to the present invention as a host.

[0072] An OLED device containing the organic electroluminescent compound of the present invention was produced as follows: A thin film (10 Ω / sq) of transparent electrode indium tin oxide (ITO) on a glass substrate for OLED devices (Samsung Corning, South Korea) was successively ultrasonically cleaned with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Next, the ITO substrate was placed on a substrate holder of a vacuum deposition apparatus. N as HI-1 4 ,N 4 '-diphenyl-N 4 ,N 4'-Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine is introduced into the cell of the vacuum deposition apparatus, and then the pressure in the chamber of the apparatus is set to 10 -6The current was controlled. Then, an electric current was applied to this cell to evaporate the introduced material, thereby forming a hole injection layer 1 with a thickness of 80 nm on the ITO substrate. Next, 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitride as HI-2 was introduced into another cell of the vacuum deposition apparatus, and then an electric current was applied to this cell to evaporate the introduced material, thereby forming a hole injection layer 2 with a thickness of 5 nm on the hole injection layer 1. N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine as HT-1 was introduced into one cell of the vacuum deposition apparatus. Then, an electric current was applied to this cell to evaporate the introduced material, thereby forming a hole transport layer 1 with a thickness of 10 nm on the hole injection layer 2. Next, N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine was introduced as HT-2 into another cell of the vacuum deposition apparatus. An electric current was applied to this cell to evaporate the introduced material, thereby forming a hole transport layer 2 with a thickness of 60 nm on the hole transport layer 1. Subsequently, compounds H1-1 and H2-2 were introduced as hosts into the two cells of the vacuum deposition apparatus, respectively, and compound D-96 was introduced as a dopant into another cell. These two host materials were evaporated at the same rate in a 1:1 ratio, and the dopant was evaporated at different rates. A doping amount of 3 wt% based on the total weight of the host and dopant was deposited to form a light-emitting layer with a thickness of 40 nm on the hole transport layer. Next, 2,4-bis(9,9-dimethyl-9H-fluoren-2yl)-6-(naphthalene-2yl)-1,3,5-triazine as ET-1 and lithium quinolate as EI-1 were evaporated at the same rate in a 1:1 ratio on two separate cells to form an electron transport layer with a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate EI-1 with a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using a separate vacuum deposition apparatus. As a result, an OLED device was produced.

[0073] The generated OLED devices exhibited the drive voltage, luminous efficiency, CIE color coordinates at a brightness of 1,000 nits, and the lifetime required for the constant current to decrease from 100% to 90% at a brightness of 5,000 nits, as provided in Table 1 below.

[0074] [ka]

[0075] Comparative Example 1-1: Generation of an OLED device using only the second host compound according to the present invention as the host.

[0076] An OLED device was manufactured in the same manner as in Device Example 1-1, except that only the second host compound was used as the host in the light-emitting layer.

[0077] The luminescence characteristics of the OLED devices produced in Device Example 1-1 and Comparative Example 1-1 are shown in Table 1 below.

[0078] [Table 1]

[0079] Device Examples 2-1 to 2-13: Generation of OLED devices by simultaneously depositing a first host compound and a second host compound according to the present invention as hosts.

[0080] An OLED device was fabricated in the same manner as in Device Example 1-1, except that the hole injection layer 2 had a thickness of 3 nm, the hole transport layer 1 had a thickness of 40 nm, the hole transport layer 2 was absent, D-25 was deposited in the emissive layer as a dopant at a doping amount of 15 wt%, and an electron transport layer with a thickness of 35 nm was deposited at an evaporation rate of 4:6. The combination of the first and second host compounds used as hosts in the emissive layer was based on Device Examples 2-1 to 2-13, as provided in Table 2 below, except that the lifetime provided in Table 2 below was required for the constant current to be reduced from 100% to 90% at a brightness of 15,000 nits.

[0081] Device Examples 2-14 to 2-18: Generation of OLED devices by co-depositing a first host compound and a second host compound according to the present invention as hosts.

[0082] OLED devices were fabricated in the same manner as in Device Examples 2-1 to 2-13, except that the hole injection layer 2 had a thickness of 3 nm, the hole transport layer 1 had a thickness of 40 nm, the hole transport layer 2 was absent, D-1 was used as a dopant in the light-emitting layer, an electron transport layer with a thickness of 35 nm was deposited at an evaporation rate of 4:6, and the combination of the first and second host compounds used as hosts in the light-emitting layer was based on Device Examples 2-14 to 2-18, as provided in Table 2 below, except that the constant current was reduced from 100% to 90% at a brightness of 15,000 nits, and the lifetime provided in Table 2 below was required.

[0083] Device Examples 3-1 to 3-8: Generation of OLED devices by co-depositing a first host compound and a second host compound according to the present invention as hosts.

[0084] OLED devices were fabricated in the same manner as in Device Examples 2-1 to 2-13, except that the hole transport layer 1 had a thickness of 10 nm, the HT-3 hole transport layer 2 had a thickness of 30 nm, D-136 was used as a dopant in the light-emitting layer, and the combination of the first and second host compounds used as hosts in the light-emitting layer was based on Device Examples 3-1 to 3-8, as provided in Table 2 below.

[0085] Device Example 3-9: Generation of an OLED device by simultaneously depositing a first host compound and a second host compound according to the present invention as a host.

[0086] An OLED device was fabricated in the same manner as in Device Examples 2-1 to 2-13, except that the hole transport layer 1 had a thickness of 10 nm, the HT-3 hole transport layer 2 had a thickness of 30 nm, D-164 was used as a dopant in the light-emitting layer, and the combination of the first and second host compounds used as hosts in the light-emitting layer was based on Device Example 3-9, as provided in Table 2 below.

[0087] Device Examples 3-10 to 3-12: Generation of OLED devices by co-depositing a first host compound and a second host compound according to the present invention as hosts.

[0088] OLED devices were fabricated in the same manner as in Device Examples 2-1 to 2-13, except that the hole transport layer 1 had a thickness of 10 nm, the HT-3 hole transport layer 2 had a thickness of 30 nm, D-168 was used as a dopant in the light-emitting layer, and the combination of the first and second host compounds used as hosts in the light-emitting layer was based on Device Examples 3-10 to 3-12, as provided in Table 2 below.

[0089] Device Example 3-13: Generation of an OLED device by simultaneously depositing a first host compound and a second host compound according to the present invention as a host.

[0090] OLED devices were fabricated in the same manner as in Device Examples 2-1 to 2-13, except that the hole transport layer 1 had a thickness of 10 nm, the HT-3 hole transport layer 2 had a thickness of 30 nm, D-180 was used as a dopant in the light-emitting layer, and the combination of the first and second host compounds used as hosts in the light-emitting layer was based on Device Example 3-13, as provided in Table 2 below.

[0091] Comparative Examples 2-1 to 2-3: Generation of OLED devices using only the first host compound according to the present invention as a host.

[0092] OLED devices were produced in the same manner as in Device Examples 2-1 to 2-13, except that the first host compound used as a host in the light-emitting layer was based on Comparative Examples 2-1 to 2-3, as provided in Table 2 below.

[0093] Comparative Examples 3-1 to 3-9: Generation of OLED devices using only the second host compound according to the present invention as the host.

[0094] OLED devices were produced in the same manner as in Device Examples 2-1 to 2-13, except that the second host compound used as a host in the light-emitting layer was based on Comparative Examples 3-1 to 3-9, as provided in Table 2 below.

[0095] Comparative Example 4-1: Generation of an OLED device using only the second host compound according to the present invention as the host.

[0096] OLED devices were produced in the same manner as in Device Examples 3-1 to 3-8, except that the second host compound used as a host in the light-emitting layer was based on Comparative Example 4-1, as provided in Table 2 below.

[0097] The luminescence characteristics of the OLED devices produced in the above-described device examples and comparative examples are shown in Table 2 below.

[0098] [Table 2-1]

[0099] [Table 2-2]

[0100] [Table 2-3]

[0101] [Table 2-4]

[0102] Device Examples 4-1 to 4-7: Generation of OLED devices by simultaneously depositing a first host compound and a second host compound according to the present invention as hosts.

[0103] An OLED device was produced in the same manner as in Device Example 1-1, except that HT-4 was used as the hole transport layer 2, and the combination of the first and second host compounds used as hosts in the light-emitting layer required the lifetime provided in Table 3 below to reduce the constant current from 100% to 95% at a brightness of 5,000 nits, based on Device Examples 4-1 to 4-7 as provided in Table 3 below.

[0104] [ka]

[0105] Comparative Examples 5-1 and 5-2: Generation of OLED devices using only the second host compound according to the present invention as a host.

[0106] OLED devices were produced in the same manner as in Device Examples 4-1 to 4-7, except that the second host compound used as a host in the light-emitting layer was based on Comparative Examples 5-1 and 5-2, as provided in Table 3 below.

[0107] The luminescence characteristics of the OLED devices produced in Device Examples 4-1 to 4-7 and Comparative Examples 5-1 and 5-2 are provided in Table 3 below.

[0108] [Table 3]

[0109] Device Examples 5-1 and 5-2: Generation of OLED devices by co-depositing a first host compound and a second host compound according to the present invention as hosts.

[0110] OLED devices were manufactured in the same manner as in Device Examples 3-1 to 3-11, except that D-134 was used as a dopant in the light-emitting layer, and the combination of the first and second host compounds used as hosts in the light-emitting layer required the lifetime provided in Table 4 below to reduce the constant current from 100% to 97% at a brightness of 15,000 nits, based on Device Examples 5-1 and 5-2 as provided in Table 4 below.

[0111] Comparative Examples 6-1 and 6-2: Generation of OLED devices using only the first host compound according to the present invention as a host.

[0112] OLED devices were produced in the same manner as in Device Examples 5-1 and 5-2, except that the first host compound used as a host in the light-emitting layer was based on Comparative Examples 6-1 and 6-2, as provided in Table 4 below.

[0113] Comparative Example 7-1: Generation of an OLED device using only the second host compound according to the present invention as the host.

[0114] OLED devices were produced in the same manner as in Device Examples 5-1 and 5-2, except that the second host compound used as a host in the light-emitting layer was based on Comparative Example 7-1, as provided in Table 4 below.

[0115] The luminescence characteristics of the OLED devices produced in Device Examples 5-1 and 5-2, Comparative Examples 6-1 and 6-2, and Comparative Example 7-1 are provided in Table 4 below.

[0116] [Table 4]

[0117] The organic electroluminescent device of the present invention provides a longer lifespan compared to conventional devices by comprising an emissive layer containing a host and a phosphorescent dopant, wherein the host consists of a multicomponent host compound, and at least the first host compound of the multicomponent host compound has a specific bicarbazole derivative containing an aryl group, and the second host compound has a specific carbazole derivative containing a nitrogen-containing heteroaryl group.

Claims

1. An organic electroluminescent 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, the host comprising a multicomponent host compound, at least one of the multicomponent host compounds being represented by the following formula 1, which is a bicarbazole derivative containing an aryl group, and the second host compound being represented by the following formula 2, which is a carbazole derivative containing a nitrogen-containing heteroaryl group. 【Chemistry 1】 During the ceremony, A １ and A ２ Each of these independently represents a deuterium-substituted or unsubstituted phenyl, or a deuterium-substituted or unsubstituted biphenyl. X １ ~X １６ Each of these independently represents hydrogen or deuterium. Ma represents a substituted or unsubstituted triazinyl compound. La represents a deuterium-substituted or unsubstituted phenylene group. Xa to Xh each independently represent hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C6-C60)aryl group, or substituted or unsubstituted 3 to 30-membered heteroaryl group. However, at least two adjacent Xa and Xb or Xh and Xg are linked to form benzofuran or benzothiophene. The aforementioned X １ ~X １６ The heteroaryl group of the X １ ~X １６ An organic electroluminescent device wherein the heteroaryl group of the substituent and the heteroaryl groups Xa to Xh each independently contain at least one heteroatom selected from B, N, O, S, P (=O), Si, and P.

2. The compound of formula 1 is represented by the following formulas 3, 4, 5, or 6, 【Chemistry 2】 During the ceremony, A １ and A ２ each independently represents deuterium-substituted or unsubstituted phenyl or deuterium-substituted or unsubstituted biphenyl, X １ ~X １６ The organic electroluminescent device according to claim 1, wherein each of these independently represents hydrogen or deuterium.

3. In equation 2, La is represented by one selected from the following equations 10 to 12: 【Transformation 3】 The organic electroluminescent device according to claim 1, wherein Xi to Xl each independently represent hydrogen or deuterium.

4. The compound represented by formula 1 is selected from the group consisting of the following compounds, in the organic electroluminescent device according to claim 1: 【Chemistry 4】

5. The compound represented by formula 2 is selected from the group consisting of the following compounds, according to claim 1, for the organic electroluminescent device: 【Transformation 5】

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