Multi-component host materials and organic electroluminescent devices comprising the same

Abstract

The present invention relates to 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 consists of a multi-component host compound; at least one first host compound of the multi-component host compound is a specific aryl-containing bicarbazole derivative, and a second host compound is a specific nitrogen-containing heteroaryl-containing carbazole derivative. According to the present invention, the organic electroluminescent device using the multi-component host compound has high efficiency and long lifetime compared to conventional devices using a single-component host compound.

Description

[0001] This patent application is a divisional application of the patent application with international application number PCT / KR2015 / 003485, international filing date of April 7, 2015, entered into the Chinese national phase as application number 201580017400.6, and entitled "Multi-component Host Material and Organic Electroluminescent Device Comprising the Same". TECHNICAL FIELD

[0002] The present application relates to a multi-component host material and an organic electroluminescent device comprising the same. BACKGROUND

[0003] An electroluminescent (EL) device is a self-light-emitting device, which has advantages of providing a wider viewing angle, a higher contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].

[0004] An organic EL device converts electrical energy into light by injecting charges into an organic light-emitting material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic EL device can be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing a host and a dopant material), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.; the materials for the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on the function. In an organic EL device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by injecting charges, and an exciton having a high energy is generated by recombination of the holes and the electrons. The organic light-emitting compound moves to an excited state using the energy, and emits light from the energy change when the organic light-emitting compound returns from the excited state to the ground state.

[0005] The most important factor that determines the luminous efficiency in an organic EL device is a light-emitting material. The light-emitting material needs to have the following characteristics: high quantum efficiency, high degree of movement of electrons and holes, formability of a uniform layer, and stability. The light-emitting material is classified into a blue light-emitting material, a green light-emitting material, and a red light-emitting material according to the color of light emission, and further includes a yellow light-emitting material or an orange light-emitting material. In addition, the light-emitting material is classified into a host material and a dopant material in terms of function. Recently, an urgent task is to develop an organic EL device having high power efficiency and long operating life. Specifically, in view of the EL characteristics required in a medium- and large-sized OLED panel, it is urgent to develop a highly superior light-emitting material to conventional light-emitting materials. To this end, preferably, as a solvent in a solid state and an energy emitter, the host material should have high purity and a suitable molecular weight so as to be deposited under vacuum. In addition, the host material needs to have a high glass transition temperature and a pyrolysis temperature to ensure thermal stability, high electrochemical stability to provide long life, easy formability of an amorphous thin film, good adhesion to adjacent layers, and no movement between layers.

[0006] A mixed system of a dopant / host material can be used as a light-emitting material to improve color purity, luminous efficiency, and stability. Generally, a device having the most superior EL characteristics includes a light-emitting layer in which a dopant is doped on a host. If a dopant / host material system is used, it is important to select a host material because the host material greatly influences the efficiency and performance of a light-emitting device.

[0007] WO 2013 / 168688 A1, Japanese Patent No. 3139321, Korean Patent No. 10-1170666, Korean Patent Application Laid-Open No. 10-2012-0013173, and WO 2013 / 112557 A1 disclose an organic EL device including a dopant / host material system. The above documents use a host component having a carbazole-carbazole skeleton, or exclude a host having a carbazole skeleton from the second and third hosts.

[0008] The present inventors have found that an organic EL device using a multi-component host compound having a specific aryl-containing dicarbazole derivative and a specific carbazole derivative including a nitrogen-containing heteroaryl has high efficiency and long life compared to using a single-component host compound in a light-emitting layer. SUMMARY

[0009] Problems to be Solved

[0010] An object of the present invention is to provide an organic EL device having high efficiency and long life.

[0011] Solution to Problem

[0012] The above object can be achieved by 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 consists of a multi-component host compound; at least one first host compound of the multi-component host compound is represented by the following Formula 1 as a specific aryl-containing biscarbazole derivative, and a second host compound is represented by the following Formula 2 as a specific nitrogen-containing heteroaryl-including carbazole derivative:

[0013]

[0014] wherein

[0015] A1and A2each independently represent a substituted or unsubstituted (C6-C30)aryl;

[0016] X1to X 16 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylaminyl; or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0017] Ma represents a substituted or unsubstituted nitrogen-containing 5- to 30-membered heteroaryl;

[0018] La represents a single bond or a substituted or unsubstituted (C6-C30)arylene;

[0019] Xa to Xh each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted 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 are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0020] the fused aromatic or heteroaromatic ring is selected from the group consisting of benzene, indole, indene, benzofuran, and benzothiophene, which can be further substituted with (C1-C10)alkyl or (C6-C15)aryl; and

[0021] the heteroaryl group contains at least one hetero atom selected from B, N, O, S, P(=O), Si, and P.

[0022] Effects of the Invention

[0023] According to the present invention, an organic EL device having high efficiency and long lifespan is provided, and a display device or a lighting device using the same can be manufactured. DETAILED DESCRIPTION

[0024] Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not intended to limit the scope of the invention in any manner.

[0025] The compound of Formula 1 is represented by Formula 3, 4, 5, or 6 below:

[0026]

[0027] wherein

[0028] A1, A2, and X1to X 16 as defined in Formula 1.

[0029] In Formula 1, A1and A2each independently represent a substituted or unsubstituted (C6-C30)aryl; preferably, a substituted or unsubstituted (C6-C18)aryl; more preferably, a (C6-C18)aryl, which is unsubstituted or substituted with a (C1-C6)alkyl, (C6-C12)aryl, or tri(C6-C12)arylsilyl; and even more preferably, a phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, rylene, tetracenyl, or fluoranthenyl.

[0030] In Formula 1, X1to X 16 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably, hydrogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted tri(C6-C12)arylsilyl, or a substituted or unsubstituted 3- to 15-membered heteroaryl; and more preferably, hydrogen, a substituted or unsubstituted (C6-C18)aryl, unsubstituted triphenylsilyl, a substituted or unsubstituted dithiophenyl, or a substituted or unsubstituted dibenzofuranyl.

[0031] The compound of Formula 2 is represented by Formula 7, 8, or 9 below:

[0032]

[0033]

[0034] wherein

[0035] V and W each independently represent a single bond, NR 15 , CR 16 R 17 , S, or O, with the proviso that both V and W do not represent a single bond and NR 15 , respectively.

[0036] A2represents a substituted or unsubstituted (C6-C30)aryl and can be bound to Xnor Xo;

[0037] L3and L4each independently represent a single bond or a substituted or unsubstituted (C6-C60)arylene;

[0038] Xi represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or is linked between adjacent substituents to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0039] Xjto Xzeach independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, -NR5R6, or -SiR7R8R9; or are linked between adjacent substituents to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

[0040] Ma, La, Xa, Xb, and Xe to Xh are as defined in Formula 2;

[0041] R5to R9each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; or are linked between adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C30)alicyclic ring or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably, hydrogen, or a substituted or unsubstituted (C6-C25)aryl; more preferably, hydrogen or an unsubstituted (C6-C18)aryl; and specifically, hydrogen, an unsubstituted phenyl, biphenyl, or fluorenyl;

[0042] R 16 and R 17 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; and

[0043] R 15 represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; preferably, a substituted or unsubstituted (C6-C30)aryl; and more preferably, a substituted or unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted naphthyl, or a substituted fluorenyl.

[0044] In Formula 2, La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene; and more preferably, a single bond, a (C6-C12)arylene, which is unsubstituted or substituted with tri(C6-C10)arylsilyl or (C6-C12)aryl.

[0045] Further, La represents a single bond, or is represented by one selected from the following Formulas 10 to 19:

[0046]

[0047]

[0048] wherein

[0049] Xi to Xp each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted 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)arylaminyl group; or are linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom ring can be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably, hydrogen, cyano, a substituted or unsubstituted (C6-C15)aryl group, a substituted or unsubstituted 10- to 20-membered heteroaryl group, or a substituted or unsubstituted tri(C6-C10)arylsilyl group; more preferably, hydrogen, cyano, a (C6-C15)aryl group, which is unsubstituted or substituted with a tri(C6-C10)arylsilyl group, or a 10- to 20-membered heteroaryl group, which is unsubstituted or substituted with a (C6-C15)aryl group.

[0050] In Formula 2, Ma represents a substituted or unsubstituted 5- to 11-membered nitrogen-containing heteroaryl group; preferably, a substituted or unsubstituted 6- to 10-membered nitrogen-containing heteroaryl group; and more preferably, a 6- to 10-membered nitrogen-containing heteroaryl group, which is substituted with a substituent selected from the group consisting of an unsubstituted (C6-C18)aryl group, a (C6-C12)aryl group substituted with cyano, a (C6-C12)aryl group substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group substituted with a tri(C6-C12)arylsilyl group, and a 6- to 15-membered heteroaryl group.

[0051] Further, Ma represents a monocyclic-based heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, or a fused ring-based heteroaryl group selected from the group consisting of benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthrydinyl, quinoxalinyl, carbazolyl, phenanthrolinyl, and the like; preferably, triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthrydinyl, or quinoxalinyl.

[0052] In this context, "(C1-C30)(alkyl)ene" means a straight-chain or branched (alkyl)ene group having 1 to 30 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and the like. "(C2-C30)Alkenyl" means a straight-chain or branched alkenyl group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethenyl, 1 -propenyl, 2-propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. "(C2-C30)Alkynyl" is a straight-chain or branched alkynyl group having 2 to 30 carbon atoms, wherein 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 -methylpent-2-ynyl, and the like. "(C3-C30)Cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "3- to 7-membered heterocycloalkyl" is a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, P(=0), Si, and P, preferably O, S, and N, and 3 to 7, preferably 5 to 7, ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. "(C6-C30)(Aryl)ene" is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, rylene, fluoranthenyl, and the like."3- to 30-membered (hetero)aryl" is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si, and P, and 3 to 30 ring main chain atoms; is a monocyclic ring or a fused ring condensed with at least one benzene ring; has preferably 3 to 20, more preferably 3 to 15 ring main chain atoms; can be partially saturated; can be a group formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond; and includes monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring condensed heteroaryl groups including benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoaxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenoxathiinyl, benzodioxolyl, and the like. "Nitrogen-containing 5- to 30-membered (hetero)aryl" is a (hetero)aryl group having at least one heteroatom N and 5 to 30 ring main chain atoms. 5 to 20 ring main chain atoms and 1 to 4 heteroatoms are preferred, and 5 to 15 ring main chain atoms are more preferred. It is a monocyclic ring or a fused ring condensed with at least one benzene ring; can be partially saturated; can be a group formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond; and includes monocyclic heteroaryl groups including pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring condensed heteroaryl groups including benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthrolinyl, and the like. "Halogen" includes F, Cl, Br, and I.

[0053] In the present document, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. The substituents of a substituted (alkylene), a substituted alkenyl group, a substituted alkynyl group, a substituted cycloalkyl group, a substituted (arylene), a substituted (heteroarylene), a substituted trialkylsilyl group, a substituted triarylsilyl group, a substituted dialkylarylsilyl group, a substituted mono- or di- arylamino group, or a substituted mono- or polycyclic (C3-C30) alicyclic ring or aromatic ring are each independently at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group, a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 3- to 30-membered heteroaryl group, which is unsubstituted or substituted with a (C6-C30)aryl group; a (C6-C30)aryl group, which is unsubstituted or substituted with a cyano group, a 3- to 30-membered heteroaryl group, or a tri(C6-C30)arylsilyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di- (C1-C30)alkylamino group; a mono- or di- (C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group. Preferably, the substituents are each independently at least one selected from the group consisting of a (C1-C6)alkyl group; a 5- to 15-membered heteroaryl group; a (C6-C18)aryl group, which is unsubstituted or substituted with a cyano group or a tri(C6-C12)arylsilyl group; a tri(C6-C12)arylsilyl group; and a (C1-C6)alkyl(C6-C12)aryl group.

[0054] The compound of Formula 1 as the first host compound can be selected from the group consisting of, but not limited to, the following compounds:

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] The compound of Formula 2 as the second host compound can be selected from the group consisting of, but not limited to, the following compounds:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] The organic EL device according to the present application can comprise an anode, a cathode, and at least one organic layer between the two electrodes, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprising a host and a phosphorescent dopant; the host consisting of a multi-component host compound; at least one first host compound of the multi-component host compound being represented by Formula 1 as a specific aryl-containing biscarbazole derivative, and a second host compound being represented by Formula 2 as a specific nitrogen-containing heteroaryl-comprising carbazole derivative.

[0076] The light-emitting layer means a layer that emits light, and can be a single layer or a multi-layer consisting of two or more layers. The concentration of the dopant compound doped into the host compound in the light-emitting layer is preferably less than 20 wt%.

[0077] The dopant included in the organic EL device of the present application is preferably one or more phosphorescent dopants. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but can be preferably selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho-metalated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metalated iridium complex compounds.

[0078] The phosphorescent dopant can be selected from the group consisting of compounds represented by the following formulae 101 to 103:

[0079]

[0080] wherein

[0081] L is selected from the following structures:

[0082]

[0083] R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl; R 101 to R 109 and R 111 to R 123 each independently represent hydrogen, deuterium, halogen; (C1-C30)alkyl which is unsubstituted or substituted with halogen; cyano, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)cycloalkyl; R 120 to R 123 are linked to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic (C3-C30)alicyclic ring or aromatic ring, for example quinoline; R 124 to R 127 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30)aryl; when R 124 to R 127 are aryl, they are linked to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic (C3-C30)alicyclic ring or aromatic ring, or a heteroaromatic ring (for example fluorene, dibenzothiophene or dibenzofuran); R 201 to R 211 each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl which is unsubstituted or substituted with halogen, or substituted or unsubstituted (C6-C30)aryl; R 208 to R 211may be attached to adjacent substituents to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic ring or aromatic ring, or heteroaromatic ring (e.g., fluorene, dibenzothiophene, or dibenzofuran); r and s each independently represent an integer of 1 to 3; each of R 100 may be the same or different; and e represents an integer of 1 to 3.

[0084] The phosphorescent dopant material includes the following:

[0085]

[0086]

[0087]

[0088]

[0089] The organic EL device of the present application can further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.

[0090] In the organic EL device of the present application, the organic layer can further include at least one metal selected from the group consisting of Group 1 metals, Group 2 metals, transition metals of Period 4, transition metals of Period 5, lanthanide series elements, and organometallics of d-transition elements, or at least one complex compound including the metal.

[0091] Preferably, in the organic electroluminescent device of the present application, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") can be disposed on the inner surface of one or both electrodes. In particular, it is preferable to dispose a chalcogenide (including oxide) layer having silicon or aluminum on the anode surface of the light-emitting intermediate layer, and to dispose a metal halide layer or a metal oxide layer on the cathode surface of the electroluminescent intermediate layer. The surface layer provides operational stability of the organic electroluminescent device. Preferably, the chalcogenide includes SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0092] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be a multi-layer to lower a hole injection barrier (or a hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, where each of the multi-layer uses two compounds at the same time. The hole transport layer or the electron blocking layer can also be a multi-layer.

[0093] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be a multi-layer to control the injection of electrons and to improve the interface properties between the light-emitting layer and the electron injection layer, where each of the multi-layer uses two compounds at the same time. The hole blocking layer or the electron transport layer can also be a multi-layer, where each of the multi-layer can use a multi-component of compounds.

[0094] Preferably, in the organic electroluminescent device of the present application, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus becomes easier to inject and transport electrons from the mixed region to the light-emitting medium. In addition, the hole transport compound is oxidized to a cation, and thus becomes easier to inject and transport holes from the mixed region to the light-emitting medium. Preferably, the oxidizing dopant includes a variety of Lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge generation layer to produce an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0095] To form each layer constituting the organic electroluminescent device of the present application, a dry film-forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as spin coating, dip coating, flow coating method, etc., can be used. When forming a layer by using the first host and the second host according to the present application, co-deposition or mixed deposition can be used.

[0096] When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvent, does not cause any problem in forming a layer.

[0097] Further, a display device or a light device can be produced by using the organic EL device of the present application.

[0098] Hereinafter, a method of producing a device by using the host compound and the dopant compound of the present application will be explained in detail with reference to the following examples:

[0099] Device Example 1-1: An OLED device was produced by co-depositing a first host compound and a second host compound according to the present application as a host Device Example 1-1: An OLED device was produced by co-depositing a first host compound and a second host compound according to the present application as a host

[0100] An OLED device comprising the organic electroluminescent compound of the present application was manufactured as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate of an OLED device (Samsung Corning, Republic of Korea) was subjected to ultrasonic washing using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine was introduced into a cell of a vacuum vapor deposition apparatus as HI-1, and then the pressure in the chamber of the apparatus was controlled to 10 -6Afterwards, current was applied to the cell to vaporize the introduced material, thereby forming a hole injection layer 1 on the ITO substrate with a thickness of 80 nm. Next, 1,4,5,8,9,12-hexaazatriphenylhexamethylcine was introduced as HI-2 into another cell of the vacuum vapor deposition apparatus, and current was applied to the cell to vaporize the introduced material, thereby forming a hole injection layer 2 on the hole injection layer 1 with a thickness of 5 nm. N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine was introduced as HT-1 into one cell of the vacuum vapor deposition apparatus. Thereafter, current was applied to the cell to vaporize the introduced material, thereby forming a hole transport layer 1 on the hole injection layer 2 with a thickness of 10 nm. Next, N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine was introduced as HT-2 into another cell of the vacuum vapor deposition apparatus, and current was applied to the cell to vaporize the introduced material, thereby forming a hole transport layer 2 on the hole transport layer 1 with a thickness of 60 nm. Thereafter, compounds H1-1 and H2-2 were introduced as hosts into two cells of the vacuum vapor deposition apparatus, respectively, and compound D-96 was introduced as a dopant into another cell. The two host materials were vaporized at the same rate of 1:1, and the dopant was vaporized at a different rate and deposited at a doping amount of 3 wt% based on the total weight of the host and dopant to form a light-emitting layer on the hole transport layer with a thickness of 40 nm. Next, 2,4-bis(9,9-dimethyl-9H-fluoren-2yl)-6-(naphthalen-2-yl)-1,3,5-triazine was vaporized as ET-1 and lithium quinolate was vaporized as EI-1 at the same rate of 1:1 on two other cells to form an electron transport layer on the light-emitting layer with a thickness of 30 nm. After depositing lithium quinolate of EI-1 as an electron injection layer on the electron transport layer with a thickness of 2 nm, a thickness of 80 nm of an Al cathode was then deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED device was manufactured.

[0101] The manufactured OLED device exhibited a driving voltage, luminous efficiency, CIE color coordinates at a luminance of 1,000 nit, and a lifetime required to reduce a constant current from 100% to 90% at a luminance of 5,000 nit as provided in Table 1 below.

[0102]

[0103] Comparative Example 1-1: An OLED device was produced by using only a second host compound according to the present application as a host Table 1

[0104] The OLED device is manufactured in the same manner as in device example 1-1, except that only the second host compound is used as the host in the light-emitting layer.

[0105] The luminescence characteristics of the OLED devices manufactured in Device Example 1-1 and Comparative Example 1-1 are provided in Table 1 below.

[0106] Device Examples 2-1 to 2-13: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host

[0107]

[0108] Device Examples 2-14 to 2-18: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host Device Examples 3-1 to 3-8: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host

[0109] The OLED device is manufactured in the same manner as in Device Example 1-1, except that the hole injection layer 2 has a thickness of 3 nm, the hole transport layer 1 has a thickness of 40 nm, the hole transport layer 2 is absent, D-25 is deposited as a dopant in the emissive layer at a doping amount of 15 wt%, and an electron transport layer with a thickness of 35 nm is deposited via an evaporation rate of 4:6. The combination of the first host compound and the second host compound used as the host in the emissive layer is based on Device Examples 2-1 to 2-13, as provided in Table 2 below, and the lifetime required for the constant current to decrease from 100% to 90% at a brightness of 15,000 nits is provided in Table 2 below.

[0110] Device Example 3-9: An OLED device was produced by co-depositing a first host compound and a second host compound according to the present application as a host Device Examples 3-10 to 3-12: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host

[0111] The OLED device is manufactured in the same manner as in Device Examples 2-1 to 2-13, except that the hole injection layer 2 has a thickness of 3 nm, the hole transport layer 1 has a thickness of 40 nm, the hole transport layer 2 is absent, D-1 is used as a dopant for the light-emitting layer, and an electron transport layer with a thickness of 35 nm is deposited via an evaporation rate of 4:6. The combination of the first host compound and the second host compound used as the host in the light-emitting layer is based on Device Examples 2-14 to 2-18, as provided in Table 2 below, and the lifetime required for the constant current to decrease from 100% to 90% at a brightness of 15,000 nits is provided in Table 2 below.

[0112] Device Example 3-13: An OLED device was produced by co-depositing a first host compound and a second host compound according to the present application as a host Comparative Examples 2-1 to 2-3: OLED devices were produced by using only a first host compound according to the present application as a host

[0113] The OLED device is manufactured in the same manner as in device examples 2-1 to 2-13, except that the hole transport layer 1 has a thickness of 10 nm, the hole transport layer 2 of HT-3 has a thickness of 30 nm, D-136 is used as a dopant for the light-emitting layer, and the combination of the first host compound and the second host compound used as the host in the light-emitting layer is based on device examples 3-1 to 3-8, as provided in Table 2 below.

[0114] Comparative Examples 3-1 to 3-9: OLED devices were produced by using only a second host compound according to the present application as a host Comparative Example 4-1: An OLED device was produced by using only a second host compound according to the present application as a host

[0115] An OLED device was manufactured in the same manner as Device Examples 2-1 to 2-13, except that the thickness of the hole transport layer 1 was 10 nm, the thickness of the hole transport layer 2 of HT-3 was 30 nm, D-164 was used as a dopant for the light-emitting layer, and the combination of the first host compound and the second host compound used as a host in the light-emitting layer was based on Device Example 3-9, as provided in Table 2 below.

[0116] Table 2 Device Examples 4-1 to 4-7: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host

[0117] An OLED device was manufactured in the same manner as Device Examples 2-1 to 2-13, except that the thickness of the hole transport layer 1 was 10 nm, the thickness of the hole transport layer 2 of HT-3 was 30 nm, D-168 was used as a dopant for the light-emitting layer, and the combination of the first host compound and the second host compound used as a host in the light-emitting layer was based on Device Examples 3-10 to 3-12, as provided in Table 2 below.

[0118] Comparative Examples 5-1 and 5-2: OLED devices were produced by using only a second host compound according to the present application as a host Table 3

[0119] An OLED device was manufactured in the same manner as Device Examples 2-1 to 2-13, except that the thickness of the hole transport layer 1 was 10 nm, the thickness of the hole transport layer 2 of HT-3 was 30 nm, D-180 was used as a dopant for the light-emitting layer, and the combination of the first host compound and the second host compound used as a host in the light-emitting layer was based on Device Example 3-13, as provided in Table 2 below.

[0120] Device Examples 5-1 and 5-2: OLED devices were produced by co-depositing a first host compound and a second host compound according to the present application as a host Comparative Examples 6-1 and 6-2: OLED devices were produced by using only a first host compound according to the present application as a host

[0121] An OLED device was manufactured in the same manner as 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.

[0122] Comparative Example 7-1: An OLED device was produced by using only a second host compound according to the present application as a host Table 4

[0123] An OLED device was manufactured in the same manner as 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.

[0124] ​ ​

[0125] OLED devices were fabricated in the same manner as 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.

[0126] The light-emitting properties of the OLED devices fabricated in the above-described Device Examples and Comparative Examples are provided in Table 2 below.

[0127] ​

[0128]

[0129]

[0130] ​ ​

[0131] OLED devices were fabricated in the same manner as Device Example 1-1, except that HT-4 was used as the hole-transporting layer 2, the combination of the first host compound and the second host compound used as a host in the light-emitting layer was based on Device Examples 4-1 to 4-7, as provided in Table 3 below, and the lifetime required for a constant current to decrease from 100% to 95% at a luminance of 5,000 nits, as provided in Table 3 below.

[0132]

[0133] ​ ​

[0134] OLED devices were fabricated in the same manner as 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.

[0135] The light-emitting properties of the OLED devices fabricated in Device Examples 4-1 to 4-7 and Comparative Examples 5-1 and 5-2 are provided in Table 3 below.

[0136] ​

[0137]

[0138] ​ ​

[0139] OLED devices were fabricated in the same manner as Device Examples 3-1 to 3-11, except that D-134 was used as the dopant in the light-emitting layer, the combination of the first host compound and the second host compound used as the host in the light-emitting layer was based on Device Examples 5-1 and 5-2, as provided in Table 4 below, and the lifetime required to decrease the constant current from 100% to 97% at a luminance of 15,000 nits, as provided in Table 4 below.

[0140] ​ ​

[0141] OLED devices were fabricated in the same manner as Device Examples 5-1 and 5-2, except that the first host compound used as the host in the light-emitting layer was based on Comparative Examples 6-1 and 6-2, as provided in Table 4 below.

[0142] ​ ​

[0143] OLED devices were fabricated in the same manner as Device Examples 5-1 and 5-2, except that the second host compound used as the host in the light-emitting layer was based on Comparative Example 7-1, as provided in Table 4 below.

[0144] The light-emitting properties of the OLED devices fabricated 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.

[0145] ​

[0146]

[0147] The organic electroluminescent device of the present application provides a longer lifetime compared to conventional devices by comprising a light-emitting layer containing a host and a phosphorescent dopant, wherein the host consists of a multi-component host compound, at least one first host compound of the multi-component host compound has a specific aryl-containing biscarbazole derivative, and a second host compound has a specific nitrogen-containing heteroaryl-including carbazole derivative.

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 consists of a multi-component host compound; at least one first host compound of the multi-component host compound is represented by the following Formula 1 as a biscarbazole derivative containing aryl, and a second host compound is represented by the following Formula 2 as a carbazole derivative including a nitrogen-containing heteroaryl: wherein A1 represents a deuterium-substituted or unsubstituted phenyl, a deuterium-substituted or unsubstituted biphenyl, or a deuterium-substituted or unsubstituted terphenyl; A2 represents a deuterium-substituted or unsubstituted biphenyl; X1to X 16 each independently represents hydrogen or deuterium; Ma represents a substituted or unsubstituted triazine, wherein, the substituents on the substituted triazine are unsubstituted (C6-C30)aryl; La represents an unsubstituted phenylene or naphthylene; Xa to Xh each independently represent hydrogen, deuterium, unsubstituted (C6-C60)aryl, unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from O and S; or are linked to each other to form a substituted or unsubstituted benzene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene, which can be further substituted with (C1-C10)alkyl or (C6-C15)aryl.

2. The organic electroluminescent device according to claim 1, wherein the compound of Formula 1 is represented by the following Formula 3, 4, 5, or 6: wherein A1 represents a deuterium-substituted or unsubstituted biphenyl; A2 represents a deuterium-substituted biphenyl; and X1to X 16 each independently represents hydrogen or deuterium.

3. The organic electroluminescent device according to claim 1, wherein the compound of Formula 2 is represented by the following Formula 7 or 9: wherein V and W each independently represent a single bond, S, or O, with the proviso that both V and W do not represent a single bond; Xi represents hydrogen, deuterium, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from O and S; Xj to Xm and Xs to Xz each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, or -SiR7R8R9; Ma, La, Xa, Xb, and Xe to Xh are as defined in Formula 2; R7 to R9 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl.

4. The organic electroluminescent device according to claim 1, wherein La in Formula 2 is represented by one selected from the following Formulas 10 to 15: wherein Xi to Xp each independently represent hydrogen or deuterium.

5. The organic electroluminescence device according to claim 1, wherein A1in Formula 1 represents unsubstituted phenyl, unsubstituted biphenyl, or unsubstituted terphenyl, A2in Formula 1 represents unsubstituted biphenyl.

6. The organic electroluminescence device according to claim 1, wherein Xa to Xh in Formula 2 each independently represent hydrogen; (C6-C15) aryl which is unsubstituted, or 10- to 20-membered heteroaryl which is unsubstituted.

7. The organic electroluminescence device according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

8. The organic electroluminescence device according to claim 1, wherein the compound represented by Formula 2 is selected from the group consisting of the following compounds:

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