US20170125699A1 - Multi-component host material and an organic electroluminescence device comprising the same - Google Patents

Multi-component host material and an organic electroluminescence device comprising the same Download PDF

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US20170125699A1
US20170125699A1 US15/301,975 US201515301975A US2017125699A1 US 20170125699 A1 US20170125699 A1 US 20170125699A1 US 201515301975 A US201515301975 A US 201515301975A US 2017125699 A1 US2017125699 A1 US 2017125699A1
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substituted
unsubstituted
arylsilyl
host
alkyl
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Hee-Choon Ahn
Young-kwang Kim
Su-Hyun Lee
Ji-Song Jun
Seon-Woo Lee
Chi-Sik Kim
Kyoung-Jin Park
Nam-Kyun Kim
Kyung-Hoon Choi
Jae-Hoon Shim
Young-jun Cho
Kyung-Joo Lee
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Definitions

  • the present invention relates to a multi-component host material and an organic electroluminescence device comprising the same.
  • An electroluminescence device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater 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 [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device is a device changing electronic energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer of an organic EL device may be comprised of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are categorized by their functions in hole injection material, hole transport material, electron blocking material, light-emitting material, electron buffer material, hole blocking material, electron transport material, electron injection material, etc.
  • the organic EL device due to an application of a voltage, holes are injected from the anode to the light-emitting layer, electrons are injected from the cathode to the light-emitting layer, and excitons of high energies are formed by a recombination of the holes and the electrons.
  • excitons of high energies are formed by a recombination of the holes and the electrons.
  • luminescent organic compounds reach an excited state, and light emission occurs by emitting light from energy due to the excited state of the luminescent organic compounds returning to a ground state.
  • a light-emitting material must have high quantum efficiency, high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable.
  • Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, additionally yellow or orange light-emitting materials.
  • Light-emitting materials can also be categorized into host and dopant materials according to their functions.
  • the host material which acts as a solvent in a solid state and transfers energy needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve long lifespan, ease of forming amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
  • a light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability.
  • an EL device having excellent characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system as a light emitting material, their selection is important.
  • the objective of the present invention is to provide an organic electroluminescent device having high efficiency and long lifespan.
  • 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 multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by the following formula 1, and a second host compound is represented by the following formula 2:
  • a 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl
  • L 1 represents a substituted or unsubstituted (C6-C30)arylene
  • X 1 to X 16 each independently represent hydrogen, deuterium, a halogen, a 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, a substitute
  • Ma represents a substituted or unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • Xa to Xh each independently represent hydrogen, deuterium, a halogen, a 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
  • an organic electroluminescent device having high efficiency and long lifespan is provided, and it is possible to manufacture a display device or a lighting device using the organic electroluminescent device.
  • organic electroluminescent device comprising the organic electroluminescent compounds of formulae 1 and 2 will be described in detail.
  • the compound represented by formula 1 can be represented by formula 3, 4, 5, or 6:
  • a 1 , A 2 , L 1 , and X 1 to X 16 are as defined in formula 1.
  • a 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl, preferably, each independently represent a substituted or unsubstituted (C6-C18)aryl, more preferably, each independently represent a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl, and even more preferably, each independently represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, or fluoranthenyl.
  • X 1 to X 16 each independently represent hydrogen, deuterium, a halogen, a 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, a substitute
  • L 1 represents a substituted or unsubstituted (C6-C30)arylene, preferably, represents a substituted or unsubstituted (C6-C15)arylene, and more preferably, represents a (C6-C15)arylene unsubstituted or substituted with a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
  • L 1 can be represented by one of formulae 7 to 19:
  • Xi to Xp each independently represent hydrogen, deuterium, a halogen, a 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, a substitute
  • Xi to Xp may each independently represent hydrogen, a halogen, a cyano, a (C1-C10)alkyl, a (C3-C20)cycloalkyl, a (C6-C12)aryl, a (C1-C6)alkyldi(C6-C12)arylsilyl, or a tri(C6-C12)arylsilyl, and more preferably, each independently represent hydrogen, a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
  • Ma represents a substituted or unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl, preferably, represents a substituted or unsubstituted nitrogen-containing (6- to 10-membered)heteroaryl, and more preferably, represents a nitrogen-containing (6- to 10-membered)heteroaryl substituted with an unsubstituted (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, or a (6- to 15-membered)heteroaryl.
  • Ma may represent a monocyclic heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, and quinoxalinyl, and preferably may represent triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, or quinoxalinyl.
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably, represents a single bond, or a substituted or unsubstituted (C6-C12)arylene, and more preferably, represents a single bond, or a (C6-C12)arylene unsubstituted or substituted with a tri(C6-C10)arylsilyl.
  • La can represent a single bond, or be represented by one of formulae 7 to 19 as above.
  • Xa to Xh each independently represent hydrogen, deuterium, a halogen, a 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, a substitute
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which 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, etc.;
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which 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-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably
  • 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.
  • a triarylsilyl as X 1 to X 16 is preferably a triphenylsilyl.
  • the first host compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • the second host compound represented by formula 2 includes the following compounds, but is not limited thereto:
  • the organic electroluminescent device comprises an anode; a cathode; and at least one organic layer between the anode and the cathode.
  • the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host and a phosphorescent dopant.
  • the host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by formula 1, and a second host compound is represented by formula 2.
  • the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi layer of which two or more layers are stacked. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound based on the host compound is less than 20 wt %.
  • the organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the dopant is preferably at least one phosphorescent dopant.
  • the dopant materials applied to the organic electroluminescent device according to the present invention are not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopant is preferably selected from compounds represented by the following formulae 101 to 103.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R 101 to R 109 , and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; adjacent substituents of R 106 to R 109 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl; and adjacent substituents of R 120 to R 123 may be
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 124 to R 127 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 205 to R 211 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • r and s each independently represent an integer of 1 to 3; where r or s is an integer of 2 or more, each of R 100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • the phosphorescent dopant materials include the following:
  • the organic electroluminescent device according to the present invention may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • At least one layer is preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiO x (1 ⁇ X ⁇ 2), AlO x (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a layer selected from a hole injection layer, a hole transport layer, or an electron blocking layer, or formed by a combination thereof can be used.
  • Multi layers can be used for the hole injection layer in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds can be simultaneously used in each layer.
  • the hole transport layer and the electron blocking layer can also be formed of multi layers.
  • a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or formed by a combination thereof can be used.
  • Multi layers can be used for the electron buffer layer in order to control the injection of the electrons and enhance the interfacial characteristics between the light-emitting layer and the electron injection layer.
  • Two compounds can be simultaneously used in each layer.
  • the hole blocking layer and the electron transport layer can also be formed of multi layers, and each layer can comprise two or more compounds.
  • 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 is preferably placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • 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.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • each layer of the organic electroluminescent device of the present invention dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
  • the first and second host compounds of the present invention may be co-evaporated or mixture-evaporated.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying an electric current to the cells for each of the materials to be evaporated.
  • a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying an electric current to the cell for the mixture to be evaporated.
  • a display system or a lighting system can be produced.
  • An OLED device was produced using the organic electroluminescent compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4′ -diphenyl-N 4 ,N 4′ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]-4,4′-diamine (compound HI-1) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 ⁇ 6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine (compound HT-1) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • N,N-di([1,1′-biphenyl]-4-yl)-4′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine (compound HT-2) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a first host compound and a second host compound were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • a dopant compound D-96 was introduced into another cell.
  • the two host materials were evaporated at 1:1 rate, while the dopant was evaporated at a different rate from the host materials, so that the dopant was deposited in a doping amount of 3 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for using only the second host compound as a host of the light-emitting layer.
  • the driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 5,000 nit to be reduced from 100% to 80% at a constant current of the OLEDs produced as above were measured.
  • Table 1 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-25 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-1 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-136 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for forming the first hole injection layer of 10 nm; forming the second hole transport layer of 30 nm using compound HT-3; using compound D-136 as the dopant of the light-emitting layer; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for forming the first hole injection layer of 10 nm; forming the second hole transport layer of 30 nm using compound HT-3; using compound D-168 as the dopant of the light-emitting layer; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for using only the first host compound as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for using only the second host compound as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 2-8 to 2-9, except for using only the second host compound as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-3, except for using only the second host compound as a host of the light-emitting layer.
  • the driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 15,000 nit to be reduced from 100% to 80% at a constant current of the OLEDs produced as above were measured.
  • Table 2 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for using compound HT-4 for the second hole transport layer, and using the compounds as listed in Table 3 below for the first host compound and the second host compound used in the host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 4-1, except for using only the second host compound of Table 3 as a host of the light-emitting layer.
  • the driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 5,000 nit to be reduced from 100% to 90% at a constant current of the OLEDs produced as above were measured.
  • Table 3 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • the organic electroluminescent device of the present invention comprises a light-emitting layer comprising a host and a phosphorus dopant, and the host consists of a specific combination of multi-component host compounds.
  • the device of the present invention provides superior lifespan characteristics to conventional devices.

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Abstract

The present invention relates to a multi-component host material and an organic electroluminescent device comprising the same. By comprising a specific combination of the multi-component host compounds, the organic electroluminescent device according to the present invention can provide high luminous efficiency and excellent lifespan characteristics.

Description

    TECHNICAL FIELD
  • The present invention relates to a multi-component host material and an organic electroluminescence device comprising the same.
    • BACKGROUND ART
  • An electroluminescence device (EL device) is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater 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 [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device (OLED) is a device changing electronic energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of an organic EL device may be comprised of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are categorized by their functions in hole injection material, hole transport material, electron blocking material, light-emitting material, electron buffer material, hole blocking material, electron transport material, electron injection material, etc. In the organic EL device, due to an application of a voltage, holes are injected from the anode to the light-emitting layer, electrons are injected from the cathode to the light-emitting layer, and excitons of high energies are formed by a recombination of the holes and the electrons. By this energy, luminescent organic compounds reach an excited state, and light emission occurs by emitting light from energy due to the excited state of the luminescent organic compounds returning to a ground state.
  • The most important factor determining luminous efficiency in an organic EL device is the light-emitting material. A light-emitting material must have high quantum efficiency, high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable. Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, additionally yellow or orange light-emitting materials. In addition, Light-emitting materials can also be categorized into host and dopant materials according to their functions. Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, materials showing better characteristics than conventional ones must be urgently developed. The host material which acts as a solvent in a solid state and transfers energy needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve long lifespan, ease of forming amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
  • A light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability. Generally, an EL device having excellent characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system as a light emitting material, their selection is important.
  • International Publication Nos. WO 2013/168688 A1 and WO 2009/060757 A1, and Japanese Patent Appln. Laying-Open No. 2013-183036 A1, etc. disclose organic electroluminescent devices using a biscarbazole derivative as a host material. However, the references fail to disclose an organic electroluminescent device using a multi-component host comprising a biscarbazole derivative and a carbazole derivative including a nitrogen-containing heteroaryl.
    • DISCLOSURE OF THE INVENTION Problems to be Solved
  • The objective of the present invention is to provide an organic electroluminescent device having high efficiency and long lifespan.
    • Solution to Problems
  • The present inventors found that the above objective 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 multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by the following formula 1, and a second host compound is represented by the following formula 2:
  • Figure US20170125699A1-20170504-C00001
  • wherein
  • A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl;
  • L1 represents a substituted or unsubstituted (C6-C30)arylene;
  • X1 to X16 each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • Figure US20170125699A1-20170504-C00002
  • wherein
  • Ma represents a substituted or unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl;
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
  • Xa to Xh each independently represent hydrogen, deuterium, a halogen, a 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 an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and the heteroaryl contains at least one hetero atom selected from B, N, O, S, P(═O), Si, and P.
    • Effects of the Invention
  • According to the present invention, an organic electroluminescent device having high efficiency and long lifespan is provided, and it is possible to manufacture a display device or a lighting device using the organic electroluminescent device.
    • EMBODIMENTS OF THE INVENTION
  • Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
  • Hereinafter, the organic electroluminescent device comprising the organic electroluminescent compounds of formulae 1 and 2 will be described in detail.
  • The compound represented by formula 1 can be represented by formula 3, 4, 5, or 6:
  • Figure US20170125699A1-20170504-C00003
  • wherein
  • A1, A2, L1, and X1 to X16 are as defined in formula 1.
  • In formula 1 above, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl, preferably, each independently represent a substituted or unsubstituted (C6-C18)aryl, more preferably, each independently represent a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl, and even more preferably, each independently represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, or fluoranthenyl.
  • In formula 1 above, X1 to X16 each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably, each independently represent hydrogen, a cyano, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C12)arylsilyl, and more preferably, each independently represent hydrogen, a cyano, a (C6-C20)aryl unsubstituted or substituted with a cyano, an unsubstituted (5- to 20-membered)heteroaryl, or an unsubstituted tri(C6-C12)arylsilyl.
  • In formula 1 above, L1 represents a substituted or unsubstituted (C6-C30)arylene, preferably, represents a substituted or unsubstituted (C6-C15)arylene, and more preferably, represents a (C6-C15)arylene unsubstituted or substituted with a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
  • In addition, L1 can be represented by one of formulae 7 to 19:
  • Figure US20170125699A1-20170504-C00004
    Figure US20170125699A1-20170504-C00005
    Figure US20170125699A1-20170504-C00006
  • wherein
  • Xi to Xp each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
  • Preferably, Xi to Xp may each independently represent hydrogen, a halogen, a cyano, a (C1-C10)alkyl, a (C3-C20)cycloalkyl, a (C6-C12)aryl, a (C1-C6)alkyldi(C6-C12)arylsilyl, or a tri(C6-C12)arylsilyl, and more preferably, each independently represent hydrogen, a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
  • In formula 2 above, Ma represents a substituted or unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl, preferably, represents a substituted or unsubstituted nitrogen-containing (6- to 10-membered)heteroaryl, and more preferably, represents a nitrogen-containing (6- to 10-membered)heteroaryl substituted with an unsubstituted (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, or a (6- to 15-membered)heteroaryl.
  • In addition, Ma may represent a monocyclic heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, and quinoxalinyl, and preferably may represent triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, or quinoxalinyl.
  • In formula 2 above, La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, preferably, represents a single bond, or a substituted or unsubstituted (C6-C12)arylene, and more preferably, represents a single bond, or a (C6-C12)arylene unsubstituted or substituted with a tri(C6-C10)arylsilyl.
  • In addition, La can represent a single bond, or be represented by one of formulae 7 to 19 as above.
  • In formula 2 above, Xa to Xh each independently represent hydrogen, deuterium, a halogen, a 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 an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably, each independently represent hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (10- to 20-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C10)arylsilyl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C6-C20) aromatic ring, and more preferably, each independently represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsilyl; a (10- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl or a cyano(C6-C12)aryl; or an unsubstituted tri(C6-C10)arylsilyl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzoindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
  • Herein, “(C1-C30)alkyl” is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which 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, etc.; “(C2-C30)alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which 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-methylbut-2-enyl, etc.; “(C2-C30)alkynyl” is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms, in which 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, etc.; “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “(3- to 7-membered)heterocycloalkyl” is a cycloalkyl having 3 to 7 ring backbone atoms, preferably 5 to 7, including at least one heteroatom selected from B, N, O, S, P(═O), Si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.; “(3- to 30-membered)heteroaryl” is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, P(═O), Si and P; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc.; “nitrogen-containing (5- to 30-membered)heteroaryl” is an aryl having 5 to 30 ring backbone atoms, preferably 5 to 20, and more preferably 5 to 15, including at least one heteroatom, N; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc. Further, “halogen” includes F, Cl, Br, and I.
  • Herein, “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 the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di-arylamino, and the substituted nitrogen-containing heteroaryl in A1, A2, L1, X1 to X16, Ma, La, and Xa to Xh in formulae 1 and 2 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a (3- to 7-membered)heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a cyano, a (3- to 30-membered)heteroaryl, or a tri(C6-C30)arylsilyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl, and preferably are at least one selected from the group consisting of a cyano, a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, a (C6-C18)aryl unsubstituted or substituted with a cyano or a tri(C6-C12)arylsilyl, a tri(C6-C12)arylsilyl, and a (C1-C6)alkyl(C6-C12)aryl.
  • In formula 1, a triarylsilyl as X1 to X16 is preferably a triphenylsilyl.
  • The first host compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • Figure US20170125699A1-20170504-C00007
    Figure US20170125699A1-20170504-C00008
    Figure US20170125699A1-20170504-C00009
    Figure US20170125699A1-20170504-C00010
    Figure US20170125699A1-20170504-C00011
    Figure US20170125699A1-20170504-C00012
    Figure US20170125699A1-20170504-C00013
    Figure US20170125699A1-20170504-C00014
    Figure US20170125699A1-20170504-C00015
    Figure US20170125699A1-20170504-C00016
    Figure US20170125699A1-20170504-C00017
    Figure US20170125699A1-20170504-C00018
    Figure US20170125699A1-20170504-C00019
    Figure US20170125699A1-20170504-C00020
    Figure US20170125699A1-20170504-C00021
    Figure US20170125699A1-20170504-C00022
    Figure US20170125699A1-20170504-C00023
    Figure US20170125699A1-20170504-C00024
    Figure US20170125699A1-20170504-C00025
    Figure US20170125699A1-20170504-C00026
    Figure US20170125699A1-20170504-C00027
    Figure US20170125699A1-20170504-C00028
    Figure US20170125699A1-20170504-C00029
    Figure US20170125699A1-20170504-C00030
    Figure US20170125699A1-20170504-C00031
    Figure US20170125699A1-20170504-C00032
    Figure US20170125699A1-20170504-C00033
    Figure US20170125699A1-20170504-C00034
    Figure US20170125699A1-20170504-C00035
    Figure US20170125699A1-20170504-C00036
    Figure US20170125699A1-20170504-C00037
    Figure US20170125699A1-20170504-C00038
    Figure US20170125699A1-20170504-C00039
    Figure US20170125699A1-20170504-C00040
    Figure US20170125699A1-20170504-C00041
    Figure US20170125699A1-20170504-C00042
    Figure US20170125699A1-20170504-C00043
    Figure US20170125699A1-20170504-C00044
    Figure US20170125699A1-20170504-C00045
    Figure US20170125699A1-20170504-C00046
    Figure US20170125699A1-20170504-C00047
    Figure US20170125699A1-20170504-C00048
    Figure US20170125699A1-20170504-C00049
    Figure US20170125699A1-20170504-C00050
    Figure US20170125699A1-20170504-C00051
    Figure US20170125699A1-20170504-C00052
    Figure US20170125699A1-20170504-C00053
    Figure US20170125699A1-20170504-C00054
    Figure US20170125699A1-20170504-C00055
    Figure US20170125699A1-20170504-C00056
    Figure US20170125699A1-20170504-C00057
    Figure US20170125699A1-20170504-C00058
    Figure US20170125699A1-20170504-C00059
    Figure US20170125699A1-20170504-C00060
    Figure US20170125699A1-20170504-C00061
    Figure US20170125699A1-20170504-C00062
  • The second host compound represented by formula 2 includes the following compounds, but is not limited thereto:
  • Figure US20170125699A1-20170504-C00063
    Figure US20170125699A1-20170504-C00064
    Figure US20170125699A1-20170504-C00065
    Figure US20170125699A1-20170504-C00066
    Figure US20170125699A1-20170504-C00067
    Figure US20170125699A1-20170504-C00068
    Figure US20170125699A1-20170504-C00069
    Figure US20170125699A1-20170504-C00070
    Figure US20170125699A1-20170504-C00071
    Figure US20170125699A1-20170504-C00072
    Figure US20170125699A1-20170504-C00073
    Figure US20170125699A1-20170504-C00074
    Figure US20170125699A1-20170504-C00075
    Figure US20170125699A1-20170504-C00076
    Figure US20170125699A1-20170504-C00077
    Figure US20170125699A1-20170504-C00078
    Figure US20170125699A1-20170504-C00079
    Figure US20170125699A1-20170504-C00080
    Figure US20170125699A1-20170504-C00081
    Figure US20170125699A1-20170504-C00082
    Figure US20170125699A1-20170504-C00083
    Figure US20170125699A1-20170504-C00084
    Figure US20170125699A1-20170504-C00085
    Figure US20170125699A1-20170504-C00086
    Figure US20170125699A1-20170504-C00087
    Figure US20170125699A1-20170504-C00088
    Figure US20170125699A1-20170504-C00089
    Figure US20170125699A1-20170504-C00090
    Figure US20170125699A1-20170504-C00091
    Figure US20170125699A1-20170504-C00092
    Figure US20170125699A1-20170504-C00093
    Figure US20170125699A1-20170504-C00094
    Figure US20170125699A1-20170504-C00095
    Figure US20170125699A1-20170504-C00096
    Figure US20170125699A1-20170504-C00097
    Figure US20170125699A1-20170504-C00098
    Figure US20170125699A1-20170504-C00099
    Figure US20170125699A1-20170504-C00100
    Figure US20170125699A1-20170504-C00101
    Figure US20170125699A1-20170504-C00102
    Figure US20170125699A1-20170504-C00103
    Figure US20170125699A1-20170504-C00104
    Figure US20170125699A1-20170504-C00105
    Figure US20170125699A1-20170504-C00106
    Figure US20170125699A1-20170504-C00107
    Figure US20170125699A1-20170504-C00108
    Figure US20170125699A1-20170504-C00109
    Figure US20170125699A1-20170504-C00110
    Figure US20170125699A1-20170504-C00111
    Figure US20170125699A1-20170504-C00112
    Figure US20170125699A1-20170504-C00113
    Figure US20170125699A1-20170504-C00114
    Figure US20170125699A1-20170504-C00115
    Figure US20170125699A1-20170504-C00116
    Figure US20170125699A1-20170504-C00117
    Figure US20170125699A1-20170504-C00118
    Figure US20170125699A1-20170504-C00119
    Figure US20170125699A1-20170504-C00120
    Figure US20170125699A1-20170504-C00121
    Figure US20170125699A1-20170504-C00122
    Figure US20170125699A1-20170504-C00123
    Figure US20170125699A1-20170504-C00124
    Figure US20170125699A1-20170504-C00125
    Figure US20170125699A1-20170504-C00126
    Figure US20170125699A1-20170504-C00127
    Figure US20170125699A1-20170504-C00128
    Figure US20170125699A1-20170504-C00129
    Figure US20170125699A1-20170504-C00130
    Figure US20170125699A1-20170504-C00131
    Figure US20170125699A1-20170504-C00132
    Figure US20170125699A1-20170504-C00133
    Figure US20170125699A1-20170504-C00134
    Figure US20170125699A1-20170504-C00135
    Figure US20170125699A1-20170504-C00136
    Figure US20170125699A1-20170504-C00137
    Figure US20170125699A1-20170504-C00138
    Figure US20170125699A1-20170504-C00139
    Figure US20170125699A1-20170504-C00140
    Figure US20170125699A1-20170504-C00141
    Figure US20170125699A1-20170504-C00142
    Figure US20170125699A1-20170504-C00143
    Figure US20170125699A1-20170504-C00144
    Figure US20170125699A1-20170504-C00145
    Figure US20170125699A1-20170504-C00146
    Figure US20170125699A1-20170504-C00147
    Figure US20170125699A1-20170504-C00148
    Figure US20170125699A1-20170504-C00149
    Figure US20170125699A1-20170504-C00150
    Figure US20170125699A1-20170504-C00151
    Figure US20170125699A1-20170504-C00152
    Figure US20170125699A1-20170504-C00153
    Figure US20170125699A1-20170504-C00154
    Figure US20170125699A1-20170504-C00155
    Figure US20170125699A1-20170504-C00156
    Figure US20170125699A1-20170504-C00157
    Figure US20170125699A1-20170504-C00158
  • Figure US20170125699A1-20170504-C00159
    Figure US20170125699A1-20170504-C00160
    Figure US20170125699A1-20170504-C00161
    Figure US20170125699A1-20170504-C00162
    Figure US20170125699A1-20170504-C00163
    Figure US20170125699A1-20170504-C00164
    Figure US20170125699A1-20170504-C00165
    Figure US20170125699A1-20170504-C00166
    Figure US20170125699A1-20170504-C00167
    Figure US20170125699A1-20170504-C00168
    Figure US20170125699A1-20170504-C00169
    Figure US20170125699A1-20170504-C00170
    Figure US20170125699A1-20170504-C00171
    Figure US20170125699A1-20170504-C00172
    Figure US20170125699A1-20170504-C00173
    Figure US20170125699A1-20170504-C00174
    Figure US20170125699A1-20170504-C00175
    Figure US20170125699A1-20170504-C00176
    Figure US20170125699A1-20170504-C00177
    Figure US20170125699A1-20170504-C00178
    Figure US20170125699A1-20170504-C00179
    Figure US20170125699A1-20170504-C00180
    Figure US20170125699A1-20170504-C00181
    Figure US20170125699A1-20170504-C00182
    Figure US20170125699A1-20170504-C00183
    Figure US20170125699A1-20170504-C00184
    Figure US20170125699A1-20170504-C00185
    Figure US20170125699A1-20170504-C00186
    Figure US20170125699A1-20170504-C00187
    Figure US20170125699A1-20170504-C00188
    Figure US20170125699A1-20170504-C00189
    Figure US20170125699A1-20170504-C00190
    Figure US20170125699A1-20170504-C00191
    Figure US20170125699A1-20170504-C00192
    Figure US20170125699A1-20170504-C00193
    Figure US20170125699A1-20170504-C00194
    Figure US20170125699A1-20170504-C00195
    Figure US20170125699A1-20170504-C00196
    Figure US20170125699A1-20170504-C00197
    Figure US20170125699A1-20170504-C00198
    Figure US20170125699A1-20170504-C00199
    Figure US20170125699A1-20170504-C00200
    Figure US20170125699A1-20170504-C00201
    Figure US20170125699A1-20170504-C00202
    Figure US20170125699A1-20170504-C00203
    Figure US20170125699A1-20170504-C00204
    Figure US20170125699A1-20170504-C00205
    Figure US20170125699A1-20170504-C00206
    Figure US20170125699A1-20170504-C00207
    Figure US20170125699A1-20170504-C00208
    Figure US20170125699A1-20170504-C00209
    Figure US20170125699A1-20170504-C00210
    Figure US20170125699A1-20170504-C00211
    Figure US20170125699A1-20170504-C00212
    Figure US20170125699A1-20170504-C00213
    Figure US20170125699A1-20170504-C00214
    Figure US20170125699A1-20170504-C00215
    Figure US20170125699A1-20170504-C00216
    Figure US20170125699A1-20170504-C00217
    Figure US20170125699A1-20170504-C00218
    Figure US20170125699A1-20170504-C00219
    Figure US20170125699A1-20170504-C00220
    Figure US20170125699A1-20170504-C00221
    Figure US20170125699A1-20170504-C00222
    Figure US20170125699A1-20170504-C00223
    Figure US20170125699A1-20170504-C00224
    Figure US20170125699A1-20170504-C00225
    Figure US20170125699A1-20170504-C00226
  • The organic electroluminescent device according to the present invention comprises an anode; a cathode; and at least one organic layer between the anode and the cathode. The organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host and a phosphorescent dopant. The host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by formula 1, and a second host compound is represented by formula 2.
  • The light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi layer of which two or more layers are stacked. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound based on the host compound is less than 20 wt %.
  • The organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • According to the organic electroluminescent device of the present invention, the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1. The dopant is preferably at least one phosphorescent dopant. The dopant materials applied to the organic electroluminescent device according to the present invention are not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • The phosphorescent dopant is preferably selected from compounds represented by the following formulae 101 to 103.
  • Figure US20170125699A1-20170504-C00227
  • wherein L is selected from the following structures:
  • Figure US20170125699A1-20170504-C00228
  • R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R101 to R109, and R111 to R123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; adjacent substituents of R106 to R109 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl; and adjacent substituents of R120 to R123 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., quinoline unsubstituted or substituted with halogen, alkyl, or aryl;
  • R124 to R127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R124 to R127 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R205 to R211 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • r and s each independently represent an integer of 1 to 3; where r or s is an integer of 2 or more, each of R100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • Specifically, the phosphorescent dopant materials include the following:
  • Figure US20170125699A1-20170504-C00229
    Figure US20170125699A1-20170504-C00230
    Figure US20170125699A1-20170504-C00231
    Figure US20170125699A1-20170504-C00232
    Figure US20170125699A1-20170504-C00233
    Figure US20170125699A1-20170504-C00234
    Figure US20170125699A1-20170504-C00235
    Figure US20170125699A1-20170504-C00236
    Figure US20170125699A1-20170504-C00237
    Figure US20170125699A1-20170504-C00238
    Figure US20170125699A1-20170504-C00239
    Figure US20170125699A1-20170504-C00240
    Figure US20170125699A1-20170504-C00241
    Figure US20170125699A1-20170504-C00242
    Figure US20170125699A1-20170504-C00243
    Figure US20170125699A1-20170504-C00244
    Figure US20170125699A1-20170504-C00245
    Figure US20170125699A1-20170504-C00246
    Figure US20170125699A1-20170504-C00247
    Figure US20170125699A1-20170504-C00248
    Figure US20170125699A1-20170504-C00249
    Figure US20170125699A1-20170504-C00250
    Figure US20170125699A1-20170504-C00251
    Figure US20170125699A1-20170504-C00252
    Figure US20170125699A1-20170504-C00253
    Figure US20170125699A1-20170504-C00254
    Figure US20170125699A1-20170504-C00255
    Figure US20170125699A1-20170504-C00256
    Figure US20170125699A1-20170504-C00257
    Figure US20170125699A1-20170504-C00258
    Figure US20170125699A1-20170504-C00259
    Figure US20170125699A1-20170504-C00260
    Figure US20170125699A1-20170504-C00261
    Figure US20170125699A1-20170504-C00262
    Figure US20170125699A1-20170504-C00263
    Figure US20170125699A1-20170504-C00264
    Figure US20170125699A1-20170504-C00265
    Figure US20170125699A1-20170504-C00266
    Figure US20170125699A1-20170504-C00267
    Figure US20170125699A1-20170504-C00268
    Figure US20170125699A1-20170504-C00269
    Figure US20170125699A1-20170504-C00270
    Figure US20170125699A1-20170504-C00271
    Figure US20170125699A1-20170504-C00272
    Figure US20170125699A1-20170504-C00273
    Figure US20170125699A1-20170504-C00274
    Figure US20170125699A1-20170504-C00275
    Figure US20170125699A1-20170504-C00276
  • The organic electroluminescent device according to the present invention may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • In addition, in the organic electroluminescent device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • According to the present invention, at least one layer (hereinafter, “a surface layer”) is preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. Specifically, a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOx(1≦X≦2), AlOx(1≦X≦1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
  • Between the anode and the light-emitting layer, a layer selected from a hole injection layer, a hole transport layer, or an electron blocking layer, or formed by a combination thereof can be used. Multi layers can be used for the hole injection layer in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds can be simultaneously used in each layer. The hole transport layer and the electron blocking layer can also be formed of multi layers.
  • Between the light-emitting layer and the cathode, a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or formed by a combination thereof can be used. Multi layers can be used for the electron buffer layer in order to control the injection of the electrons and enhance the interfacial characteristics between the light-emitting layer and the electron injection layer. Two compounds can be simultaneously used in each layer. The hole blocking layer and the electron transport layer can also be formed of multi layers, and each layer can comprise two or more compounds.
  • In the organic electroluminescent device according to 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 is preferably 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 it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent 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. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • In order to form each layer of the organic electroluminescent device of the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used. The first and second host compounds of the present invention may be co-evaporated or mixture-evaporated.
  • When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • Herein, a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying an electric current to the cells for each of the materials to be evaporated. Herein, a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying an electric current to the cell for the mixture to be evaporated.
  • By using the organic electroluminescent device of the present invention, a display system or a lighting system can be produced.
  • Hereinafter, the luminescent properties of the device comprising the host compound of the present invention will be explained in detail with reference to the following examples.
    • Device Examples 1-1 to 1-6: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced using the organic electroluminescent compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. N4,N4′-diphenyl-N4,N4′-bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]-4,4′-diamine (compound HI-1) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10−6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine (compound HT-1) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Afterwards, N,N-di([1,1′-biphenyl]-4-yl)-4′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine (compound HT-2) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. As a host material, a first host compound and a second host compound were introduced into two cells of the vacuum vapor depositing apparatus, respectively. A dopant compound D-96 was introduced into another cell. The two host materials were evaporated at 1:1 rate, while the dopant was evaporated at a different rate from the host materials, so that the dopant was deposited in a doping amount of 3 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer. 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (compound ET-1) and lithium quinolate (compound EI-1) were then introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at 1:1 rate to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate (compound EI-1) as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. Thus, an OLED device was produced.
  • Figure US20170125699A1-20170504-C00277
    Figure US20170125699A1-20170504-C00278
    Figure US20170125699A1-20170504-C00279
    • Comparative Examples 1-1 to 1-3: Preparation of an OLED Device Using Only the Second Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for using only the second host compound as a host of the light-emitting layer.
  • The driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 5,000 nit to be reduced from 100% to 80% at a constant current of the OLEDs produced as above were measured.
  • Table 1 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • TABLE 1
    Voltage Efficiency Color Lifespan
    Device No. HTL Host Dopant [V] [cd/A] Coordinate (x, y) [hr]
    Example HT-1/HT-2 H1-1:H2-2 D-96 4.4 27.5 0.664, 0.335 1,280
    1-1
    Example HT-1/HT-2 H1-7:H2-29 D-96 3.9 27.7 0.665, 0.332 550
    1-2
    Example HT-1/HT-2 H1-19:H2-29 D-96 4.1 24.6 0.664, 0.332 470
    1-3
    Example HT-1/HT-2 H1-36:H2-154 D-96 4.6 27.8 0.663, 0.335 1,530
    1-4
    Example HT-1/HT-2 H1-36:H2-29 D-96 3.7 28.2 0.666, 0.331 780
    1-5
    Example HT-1/HT-2 H1-36:H2-155 D-96 4.6 26.9 0.664, 0.335 970
    1-6
    Comp. Ex. HT-1/HT-2 H2-2 D-96 4.1 28.2 0.662, 0.337 300
    1-1
    Comp. Ex. HT-1/HT-2 H2-154 D-96 4.5 27.1 0.662, 0.337 420
    1-2
    Comp. Ex. HT-1/HT-2 H2-29 D-96 3.6 27.5 0.668, 0.331 310
    1-3
    • Device Examples 2-1 to 2-7: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-25 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Device Examples 2-8 to 2-9: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-1 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Device Example 2-10: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for forming the second hole injection layer of 3 nm; forming the first hole transport layer of 40 nm; not forming the second hole transport layer; doping compound D-136 as the dopant of the light-emitting layer in a doping amount of 15 wt % based on the total amount of the host and dopant; forming the electron transport layer of 35 nm by evaporating 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine and lithium quinolate at a rate of 4:6; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Device Examples 3-1 to 3-3: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for forming the first hole injection layer of 10 nm; forming the second hole transport layer of 30 nm using compound HT-3; using compound D-136 as the dopant of the light-emitting layer; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Device Example 3-4: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for forming the first hole injection layer of 10 nm; forming the second hole transport layer of 30 nm using compound HT-3; using compound D-168 as the dopant of the light-emitting layer; and using other combinations for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Comparative Examples 2-1 to 2-3: Preparation of an OLED Device Using Only the First Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for using only the first host compound as a host of the light-emitting layer.
    • Comparative Examples 3-1 to 3-3: Preparation of an OLED Device Using Only the Second Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-7, except for using only the second host compound as a host of the light-emitting layer.
    • Comparative Examples 3-4 to 3-6: Preparation of an OLED Device Using Only the Second Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Examples 2-8 to 2-9, except for using only the second host compound as a host of the light-emitting layer.
    • Comparative Examples 4-1 to 4-3: Preparation of an OLED Device Using Only the Second Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-3, except for using only the second host compound as a host of the light-emitting layer.
  • The driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 15,000 nit to be reduced from 100% to 80% at a constant current of the OLEDs produced as above were measured.
  • Table 2 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • TABLE 2
    Color
    Voltage Efficiency Coordinate Lifespan
    Device No. HTL Host Dopant [V] [cd/A] (x, y) [hr]
    Example HT-1 H1-1:H2-25 D-25 3.2 49.8 0.301, 0.658 350
    2-1
    Example HT-1 H1-1:H2-31 D-25 3 57.1 0.308, 0.655 380
    2-2
    Example HT-1 H1-1:H2-48 D-25 2.9 56.8 0.305, 0.656 400
    2-3
    Example HT-1 H1-1:H2-101 D-25 3 55.5 0.303, 0.657 230
    2-4
    Example HT-1 H1-1:H2-34 D-25 3.1 58.1 0.306, 0.655 440
    2-5
    Example HT-1 H1-4:H2-31 D-25 3 53.3 0.304, 0.656 120
    2-6
    Example HT-1 H1-37:H2-31 D-25 3 53.7 0.306, 0.655 300
    2-7
    Example HT-1 H1-1:H2-31 D-1 2.9 53 0.321, 0.656 560
    2-8
    Example HT-1 H1-1:H2-48 D-1 2.8 55.3 0.319, 0.657 550
    2-9
    Example HT-1 H1-113:H2-31 D-136 2.8 59.4 0.331, 0.655 600
    2-10
    Example HT-1/HT-3 H1-1:H2-48 D-136 3.1 67.5 0.326, 0.658 590
    3-1
    Example HT-1/HT-3 H1-1:H2-273 D-136 3.1 66.2 0.328, 0.657 700
    3-2
    Example HT-1/HT-3 H1-113:H2-125 D-136 3.1 65.8 0.329, 0.657 700
    3-3
    Example HT-1/HT-3 H1-1:H2-273 D-168 3.0 57.2 0.288, 0.665 450
    3-4
    Comp. Ex. HT-1 H1-1 D-25 6.8 3.1 0.301, 0.653 x
    2-1
    Comp. Ex. HT-1 H1-4 D-25 7.2 3.6 0.295, 0.658 x
    2-2
    Comp. Ex. HT-1 H1-37 D-25 7.0 3.0 0.302, 0.653 x
    2-3
    Comp. Ex. HT-1 H2-31 D-25 2.9 42.8 0.314, 0.652 100
    3-1
    Comp. Ex. HT-1 H2-101 D-25 2.8 50.3 0.315, 0.651  60
    3-2
    Comp. Ex. HT-1 H2-34 D-25 2.7 49.2 0.312, 0.652 100
    3-3
    Comp. Ex. HT-1 H2-31 D-1 2.9 33.5 0.323, 0.653 390
    3-4
    Comp. Ex. HT-1 H2-48 D-1 2.6 41.2 0.325, 0.653 380
    3-5
    Comp. Ex. HT-1 H2-87 D-1 2.8 37.9 0.323, 0.653 420
    3-6
    Comp. Ex. HT-1/HT-3 H2-48 D-136 2.6 51.9 0.334, 0.652 490
    4-1
    Comp. Ex. HT-1/HT-3 H2-125 D-136 3.0 64.9 0.337, 0.649 360
    4-2
    Comp. Ex. HT-1/HT-3 H2-273 D-136 3.3 68.2 0.332, 0.654 440
    4-3
    • Device Example 4-1: Preparation of an OLED Device by Co-Evaporating the First Host Compound and the Second Host Compound of the Present Invention
  • An OLED device was produced in the same manner as in Device Examples 1-1 to 1-6, except for using compound HT-4 for the second hole transport layer, and using the compounds as listed in Table 3 below for the first host compound and the second host compound used in the host of the light-emitting layer.
    • Comparative Example 5-1: Preparation of an OLED Device Using Only the Second Host Compound as a Host
  • An OLED device was produced in the same manner as in Device Example 4-1, except for using only the second host compound of Table 3 as a host of the light-emitting layer.
  • The driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and the time taken for the luminance at 5,000 nit to be reduced from 100% to 90% at a constant current of the OLEDs produced as above were measured.
  • Table 3 below shows the luminous characteristics of the organic electroluminescent devices produced as in the examples above.
  • TABLE 3
    Voltage Efficiency Color Lifespan
    Device No. HTL Host Dopant [V] [cd/A] Coordinate (x, y) [hr]
    Example HT-1/HT-4 H1-7:H2-41 D-96 3.4 30.7 0.665, 0.333 400
    4-1
    Comp. Ex. HT-1/HT-4 H2-41 D-96 3.1 28.3 0.668, 0.331 300
    5-1
  • The organic electroluminescent device of the present invention comprises a light-emitting layer comprising a host and a phosphorus dopant, and the host consists of a specific combination of multi-component host compounds. The device of the present invention provides superior lifespan characteristics to conventional devices.

Claims (9)

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 multi-component host compounds, at least a first host compound of the multi-component host compounds is represented by the following formula 1, and a second host compound is represented by the following formula 2.
Figure US20170125699A1-20170504-C00280
wherein
A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl;
L1 represents a substituted or unsubstituted (C6-C30)arylene;
X1 to X16 each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
Figure US20170125699A1-20170504-C00281
wherein
Ma represents a substituted or unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl;
La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
Xa to Xh each independently represent hydrogen, deuterium, a halogen, a 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 an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, P(═O), Si, and P.
2. The organic electroluminescent device according to claim 1, wherein in formula 1,
A1 and A2 each independently are selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, and fluoranthenyl.
3. The organic electroluminescent device according to claim 1, wherein in formula 1,
L1 is represented by one of the following formulae 7 to 19:
Figure US20170125699A1-20170504-C00282
Figure US20170125699A1-20170504-C00283
Figure US20170125699A1-20170504-C00284
wherein
Xi to Xp each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
4. The organic electroluminescent device according to claim 1, wherein in formula 2,
Ma represents a monocyclic heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, and quinoxalinyl.
5. The organic electroluminescent device according to claim 1, wherein in formula 2,
La is a single bond, or represented by one of the following formulae 7 to 19:
Figure US20170125699A1-20170504-C00285
Figure US20170125699A1-20170504-C00286
Figure US20170125699A1-20170504-C00287
wherein
Xi to Xp each independently represent hydrogen, deuterium, a halogen, a 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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
6. The organic electroluminescent device according to claim 1, wherein in formula 2,
Xa to Xh each independently represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsilyl; a (10- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl or a cyano(C6-C12)aryl; or an unsubstituted tri(C6-C10)arylsilyl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzoindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
7. The organic electroluminescent device according to claim 1, wherein in formula 1, a triarylsilyl as X1 to X16 is a triphenylsilyl.
8. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
Figure US20170125699A1-20170504-C00288
Figure US20170125699A1-20170504-C00289
Figure US20170125699A1-20170504-C00290
Figure US20170125699A1-20170504-C00291
Figure US20170125699A1-20170504-C00292
Figure US20170125699A1-20170504-C00293
Figure US20170125699A1-20170504-C00294
Figure US20170125699A1-20170504-C00295
Figure US20170125699A1-20170504-C00296
Figure US20170125699A1-20170504-C00297
Figure US20170125699A1-20170504-C00298
Figure US20170125699A1-20170504-C00299
Figure US20170125699A1-20170504-C00300
Figure US20170125699A1-20170504-C00301
Figure US20170125699A1-20170504-C00302
Figure US20170125699A1-20170504-C00303
Figure US20170125699A1-20170504-C00304
Figure US20170125699A1-20170504-C00305
Figure US20170125699A1-20170504-C00306
Figure US20170125699A1-20170504-C00307
Figure US20170125699A1-20170504-C00308
Figure US20170125699A1-20170504-C00309
Figure US20170125699A1-20170504-C00310
Figure US20170125699A1-20170504-C00311
Figure US20170125699A1-20170504-C00312
Figure US20170125699A1-20170504-C00313
Figure US20170125699A1-20170504-C00314
Figure US20170125699A1-20170504-C00315
9. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
Figure US20170125699A1-20170504-C00316
Figure US20170125699A1-20170504-C00317
Figure US20170125699A1-20170504-C00318
Figure US20170125699A1-20170504-C00319
Figure US20170125699A1-20170504-C00320
Figure US20170125699A1-20170504-C00321
Figure US20170125699A1-20170504-C00322
Figure US20170125699A1-20170504-C00323
Figure US20170125699A1-20170504-C00324
Figure US20170125699A1-20170504-C00325
Figure US20170125699A1-20170504-C00326
Figure US20170125699A1-20170504-C00327
Figure US20170125699A1-20170504-C00328
Figure US20170125699A1-20170504-C00329
Figure US20170125699A1-20170504-C00330
Figure US20170125699A1-20170504-C00331
Figure US20170125699A1-20170504-C00332
Figure US20170125699A1-20170504-C00333
Figure US20170125699A1-20170504-C00334
Figure US20170125699A1-20170504-C00335
Figure US20170125699A1-20170504-C00336
Figure US20170125699A1-20170504-C00337
Figure US20170125699A1-20170504-C00338
Figure US20170125699A1-20170504-C00339
Figure US20170125699A1-20170504-C00340
Figure US20170125699A1-20170504-C00341
Figure US20170125699A1-20170504-C00342
Figure US20170125699A1-20170504-C00343
Figure US20170125699A1-20170504-C00344
Figure US20170125699A1-20170504-C00345
Figure US20170125699A1-20170504-C00346
Figure US20170125699A1-20170504-C00347
Figure US20170125699A1-20170504-C00348
Figure US20170125699A1-20170504-C00349
Figure US20170125699A1-20170504-C00350
Figure US20170125699A1-20170504-C00351
Figure US20170125699A1-20170504-C00352
Figure US20170125699A1-20170504-C00353
Figure US20170125699A1-20170504-C00354
Figure US20170125699A1-20170504-C00355
Figure US20170125699A1-20170504-C00356
Figure US20170125699A1-20170504-C00357
Figure US20170125699A1-20170504-C00358
Figure US20170125699A1-20170504-C00359
Figure US20170125699A1-20170504-C00360
Figure US20170125699A1-20170504-C00361
Figure US20170125699A1-20170504-C00362
Figure US20170125699A1-20170504-C00363
Figure US20170125699A1-20170504-C00364
Figure US20170125699A1-20170504-C00365
Figure US20170125699A1-20170504-C00366
Figure US20170125699A1-20170504-C00367
Figure US20170125699A1-20170504-C00368
Figure US20170125699A1-20170504-C00369
Figure US20170125699A1-20170504-C00370
Figure US20170125699A1-20170504-C00371
Figure US20170125699A1-20170504-C00372
Figure US20170125699A1-20170504-C00373
Figure US20170125699A1-20170504-C00374
Figure US20170125699A1-20170504-C00375
Figure US20170125699A1-20170504-C00376
Figure US20170125699A1-20170504-C00377
Figure US20170125699A1-20170504-C00378
Figure US20170125699A1-20170504-C00379
Figure US20170125699A1-20170504-C00380
Figure US20170125699A1-20170504-C00381
Figure US20170125699A1-20170504-C00382
Figure US20170125699A1-20170504-C00383
Figure US20170125699A1-20170504-C00384
Figure US20170125699A1-20170504-C00385
Figure US20170125699A1-20170504-C00386
Figure US20170125699A1-20170504-C00387
Figure US20170125699A1-20170504-C00388
Figure US20170125699A1-20170504-C00389
Figure US20170125699A1-20170504-C00390
Figure US20170125699A1-20170504-C00391
Figure US20170125699A1-20170504-C00392
Figure US20170125699A1-20170504-C00393
Figure US20170125699A1-20170504-C00394
Figure US20170125699A1-20170504-C00395
Figure US20170125699A1-20170504-C00396
Figure US20170125699A1-20170504-C00397
Figure US20170125699A1-20170504-C00398
Figure US20170125699A1-20170504-C00399
Figure US20170125699A1-20170504-C00400
Figure US20170125699A1-20170504-C00401
Figure US20170125699A1-20170504-C00402
Figure US20170125699A1-20170504-C00403
Figure US20170125699A1-20170504-C00404
Figure US20170125699A1-20170504-C00405
Figure US20170125699A1-20170504-C00406
Figure US20170125699A1-20170504-C00407
Figure US20170125699A1-20170504-C00408
Figure US20170125699A1-20170504-C00409
Figure US20170125699A1-20170504-C00410
Figure US20170125699A1-20170504-C00411
Figure US20170125699A1-20170504-C00412
Figure US20170125699A1-20170504-C00413
Figure US20170125699A1-20170504-C00414
Figure US20170125699A1-20170504-C00415
Figure US20170125699A1-20170504-C00416
Figure US20170125699A1-20170504-C00417
Figure US20170125699A1-20170504-C00418
Figure US20170125699A1-20170504-C00419
Figure US20170125699A1-20170504-C00420
Figure US20170125699A1-20170504-C00421
Figure US20170125699A1-20170504-C00422
Figure US20170125699A1-20170504-C00423
Figure US20170125699A1-20170504-C00424
Figure US20170125699A1-20170504-C00425
Figure US20170125699A1-20170504-C00426
Figure US20170125699A1-20170504-C00427
Figure US20170125699A1-20170504-C00428
Figure US20170125699A1-20170504-C00429
Figure US20170125699A1-20170504-C00430
Figure US20170125699A1-20170504-C00431
Figure US20170125699A1-20170504-C00432
Figure US20170125699A1-20170504-C00433
Figure US20170125699A1-20170504-C00434
Figure US20170125699A1-20170504-C00435
Figure US20170125699A1-20170504-C00436
Figure US20170125699A1-20170504-C00437
Figure US20170125699A1-20170504-C00438
Figure US20170125699A1-20170504-C00439
Figure US20170125699A1-20170504-C00440
Figure US20170125699A1-20170504-C00441
Figure US20170125699A1-20170504-C00442
Figure US20170125699A1-20170504-C00443
Figure US20170125699A1-20170504-C00444
Figure US20170125699A1-20170504-C00445
Figure US20170125699A1-20170504-C00446
Figure US20170125699A1-20170504-C00447
Figure US20170125699A1-20170504-C00448
Figure US20170125699A1-20170504-C00449
Figure US20170125699A1-20170504-C00450
Figure US20170125699A1-20170504-C00451
Figure US20170125699A1-20170504-C00452
Figure US20170125699A1-20170504-C00453
Figure US20170125699A1-20170504-C00454
Figure US20170125699A1-20170504-C00455
Figure US20170125699A1-20170504-C00456
Figure US20170125699A1-20170504-C00457
Figure US20170125699A1-20170504-C00458
Figure US20170125699A1-20170504-C00459
Figure US20170125699A1-20170504-C00460
Figure US20170125699A1-20170504-C00461
Figure US20170125699A1-20170504-C00462
Figure US20170125699A1-20170504-C00463
Figure US20170125699A1-20170504-C00464
Figure US20170125699A1-20170504-C00465
Figure US20170125699A1-20170504-C00466
Figure US20170125699A1-20170504-C00467
Figure US20170125699A1-20170504-C00468
Figure US20170125699A1-20170504-C00469
Figure US20170125699A1-20170504-C00470
Figure US20170125699A1-20170504-C00471
Figure US20170125699A1-20170504-C00472
Figure US20170125699A1-20170504-C00473
Figure US20170125699A1-20170504-C00474
Figure US20170125699A1-20170504-C00475
Figure US20170125699A1-20170504-C00476
Figure US20170125699A1-20170504-C00477
Figure US20170125699A1-20170504-C00478
Figure US20170125699A1-20170504-C00479
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170294613A1 (en) * 2016-04-07 2017-10-12 Samsung Display Co., Ltd. Organic light-emitting device
US20170346022A1 (en) * 2016-05-25 2017-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US9947878B2 (en) 2014-08-20 2018-04-17 Lg Chem, Ltd. Organic light-emitting device
US20180312514A1 (en) * 2017-05-01 2018-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US20190013490A1 (en) * 2016-11-16 2019-01-10 Lg Chem, Ltd. Organic light emitting device
EP3643761A1 (en) 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, organic electroluminescence device material, composition film, organic electroluminescence device, and electronic device
US20200190121A1 (en) * 2018-12-14 2020-06-18 Cynora Gmbh Organic electroluminescent devices comprising host compounds
US20200343450A1 (en) * 2018-01-11 2020-10-29 Lg Chem, Ltd. Organic light-emitting diode
US20210028370A1 (en) * 2018-03-29 2021-01-28 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and electronic device therefor
US11205755B2 (en) * 2016-07-29 2021-12-21 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using same, and electronic device thereof
US11271165B2 (en) * 2016-07-14 2022-03-08 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element
US11339132B2 (en) * 2016-01-21 2022-05-24 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
US11424417B2 (en) 2018-11-16 2022-08-23 Samsung Display Co., Ltd. Organic electroluminescence device and compound for organic electroluminescence device
US11462693B2 (en) * 2018-11-23 2022-10-04 Samsung Display Co., Ltd. Organic electroluminescence device
US11482681B2 (en) 2018-07-27 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
US20220367820A1 (en) * 2020-03-31 2022-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US11751473B2 (en) 2016-07-26 2023-09-05 Lg Chem, Ltd. Organic light emitting element
US11985893B2 (en) 2019-11-08 2024-05-14 Samsung Display Co., Ltd. Organic electroluminescence device and aromatic compound for organic electroluminescence device
US12534665B2 (en) 2019-04-15 2026-01-27 Samsung Display Co., Ltd. Organometallic compound, organic light-emitting device including the same, and apparatus including the light-emitting device
US12593606B2 (en) 2021-07-16 2026-03-31 Samsung Display Co., Ltd. Organic light-emitting device
US12598909B2 (en) 2018-11-26 2026-04-07 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101829745B1 (en) 2014-01-24 2018-02-19 삼성에스디아이 주식회사 Organic compound and composition and organic optoelectric device and display device
US9741941B2 (en) * 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
KR20150141147A (en) * 2014-06-09 2015-12-17 롬엔드하스전자재료코리아유한회사 An organic electroluminescent compound and an organic electroluminescent device comprising the same
KR102357467B1 (en) 2014-07-22 2022-02-04 롬엔드하스전자재료코리아유한회사 Organic Electroluminescence Device
KR102502306B1 (en) * 2014-07-22 2023-02-23 롬엔드하스전자재료코리아유한회사 Organic Electroluminescence Device
KR102430648B1 (en) * 2014-09-05 2022-08-09 롬엔드하스전자재료코리아유한회사 A Hole Transport Material and an Organic Electroluminescent Device Comprising the Same
KR102530113B1 (en) 2014-10-23 2023-05-10 롬엔드하스전자재료코리아유한회사 Novel organic electroluminescent compounds and an organic electroluminescent device comprising the same
KR102503311B1 (en) * 2014-12-10 2023-02-28 롬엔드하스전자재료코리아유한회사 Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same
CN107592860B (en) * 2015-04-24 2020-11-03 三星Sdi株式会社 Organic compounds, compositions and organic photodiodes
US20180072945A1 (en) * 2015-04-27 2018-03-15 Konica Minolta, Inc. Material for organic electroluminescent elements, organic electroluminescent element, display device and lighting device
KR102059021B1 (en) 2015-06-19 2019-12-24 삼성에스디아이 주식회사 Composition for organic optoelectronic device, organic optoelectric device and display device
WO2016208873A1 (en) 2015-06-26 2016-12-29 Rohm And Haas Electronic Materials Korea Ltd. Multi-component host material and organic electroluminescent device comprising the same
KR20170001552A (en) 2015-06-26 2017-01-04 롬엔드하스전자재료코리아유한회사 Multi-component host material and organic electroluminescent device comprising the same
KR102837349B1 (en) * 2015-07-20 2025-07-24 듀폰스페셜티머터리얼스코리아 유한회사 Luminescent Material for Delayed Fluorescence and Organic Electroluminescent Device Comprising the Same
KR102024981B1 (en) * 2015-08-21 2019-09-24 주식회사 엘지화학 Compound and organic electronic device comprising the same
US10270041B2 (en) * 2015-08-28 2019-04-23 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
KR102460657B1 (en) 2015-08-31 2022-10-28 삼성전자주식회사 Organic light emitting device including the same
KR101946020B1 (en) * 2015-09-10 2019-02-08 엘티소재주식회사 Hetero-cyclic compound and organic light emitting device using the same
WO2017069442A1 (en) * 2015-10-23 2017-04-27 삼성에스디아이 주식회사 Composition for organic optoelectronic element, organic optoelectronic element, and display device
KR20170075114A (en) 2015-12-22 2017-07-03 삼성디스플레이 주식회사 Organic light emitting device
KR20170075122A (en) 2015-12-22 2017-07-03 삼성디스플레이 주식회사 Organic light emitting device
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GB201523037D0 (en) * 2015-12-29 2016-02-10 Univ St Andrews Light emitting compounds
EP3190164B1 (en) 2016-01-05 2019-07-24 Samsung Electronics Co., Ltd Composition, thin film including the composition, and organic light-emitting device including the composition or the thin film
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WO2017200210A1 (en) * 2016-05-17 2017-11-23 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same
KR102836856B1 (en) * 2016-05-17 2025-07-23 듀폰스페셜티머터리얼스코리아 유한회사 Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same
KR102054276B1 (en) 2016-06-29 2019-12-10 삼성에스디아이 주식회사 Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
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KR102054277B1 (en) * 2016-07-29 2019-12-10 삼성에스디아이 주식회사 Composition for organic optoelectronic device and organic optoelectronic device and display device
KR102715029B1 (en) 2016-08-10 2024-10-10 삼성전자주식회사 Silyl-based compound and organic light-emitting device including the same
CN106432051B (en) * 2016-09-20 2019-02-22 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its preparation method and application
KR102639854B1 (en) 2016-10-31 2024-02-22 엘지디스플레이 주식회사 Organic compounds and litht emitting diode and organic light emittig diode display device using the compounds
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WO2018131866A1 (en) * 2017-01-10 2018-07-19 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device
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WO2019235857A1 (en) * 2018-06-08 2019-12-12 삼성에스디아이 주식회사 Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device
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CN119842390B (en) * 2023-10-11 2026-03-20 阜阳欣奕华新材料科技股份有限公司 A composition and an organic electroluminescent device

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004071500A (en) * 2002-08-09 2004-03-04 Konica Minolta Holdings Inc Organic electroluminescence element and display device
JP2009029726A (en) * 2007-07-25 2009-02-12 Toyo Ink Mfg Co Ltd Compound having carbazolyl group and use thereof
JP2009057307A (en) * 2007-08-31 2009-03-19 Toyo Ink Mfg Co Ltd Compound having carbazolyl group and use thereof
US20090091253A1 (en) * 2006-03-17 2009-04-09 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
US20120068170A1 (en) * 2009-05-29 2012-03-22 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2013058343A1 (en) * 2011-10-21 2013-04-25 出光興産株式会社 Organic electroluminescence element and material for organic electroluminescence element
WO2013146942A1 (en) * 2012-03-28 2013-10-03 出光興産株式会社 Novel compound, material for organic electroluminescence element, and organic electroluminescence element
US20140151647A1 (en) * 2011-12-05 2014-06-05 Yumiko Mizuki Material for organic electroluminescence device and organic electroluminescence device

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7485376B2 (en) * 2003-03-26 2009-02-03 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, and display
US8541112B2 (en) 2006-12-13 2013-09-24 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
WO2009060757A1 (en) 2007-11-08 2009-05-14 Konica Minolta Holdings, Inc. Organic electroluminescent device, display device and illuminating device
US8986858B2 (en) * 2010-02-26 2015-03-24 Nippon Steel & Sumikin Chemical Co., Ltd. Organic electroluminescent device
EP2694619A4 (en) * 2011-05-03 2014-10-22 Rohm & Haas Elect Mat NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
KR101993015B1 (en) * 2011-06-24 2019-06-25 이데미쓰 고산 가부시키가이샤 Organic electroluminescent element
US9530969B2 (en) * 2011-12-05 2016-12-27 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device
JP6060095B2 (en) * 2012-02-03 2017-01-11 出光興産株式会社 Carbazole compound, material for organic electroluminescence device, and organic electroluminescence device
JP5765271B2 (en) 2012-03-02 2015-08-19 コニカミノルタ株式会社 Organic electroluminescence element, display device and lighting device
JP2015135836A (en) * 2012-03-29 2015-07-27 出光興産株式会社 Organic electroluminescent element and material for organic electroluminescent element
WO2013145923A1 (en) * 2012-03-30 2013-10-03 出光興産株式会社 Organic electroluminescent element
KR20130112342A (en) * 2012-04-03 2013-10-14 롬엔드하스전자재료코리아유한회사 Novel carbazole compounds and organic electroluminescence device containing the same
WO2013168688A1 (en) * 2012-05-10 2013-11-14 コニカミノルタ株式会社 Organic electroluminescence element, illumination device, and display device
DE102013208844A1 (en) * 2012-06-01 2013-12-05 Semiconductor Energy Laboratory Co., Ltd. Light emitting element, light emitting device, display device, electronic device and lighting device
US9966539B2 (en) * 2012-08-31 2018-05-08 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
JP6381874B2 (en) * 2013-07-18 2018-08-29 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Material for organic electroluminescence device and organic electroluminescence device using the same

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004071500A (en) * 2002-08-09 2004-03-04 Konica Minolta Holdings Inc Organic electroluminescence element and display device
US20090091253A1 (en) * 2006-03-17 2009-04-09 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
JP2009029726A (en) * 2007-07-25 2009-02-12 Toyo Ink Mfg Co Ltd Compound having carbazolyl group and use thereof
JP2009057307A (en) * 2007-08-31 2009-03-19 Toyo Ink Mfg Co Ltd Compound having carbazolyl group and use thereof
US20120068170A1 (en) * 2009-05-29 2012-03-22 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2013058343A1 (en) * 2011-10-21 2013-04-25 出光興産株式会社 Organic electroluminescence element and material for organic electroluminescence element
US20140299865A1 (en) * 2011-10-21 2014-10-09 Idemitsu Kosan Co., Ltd. Organic electroluminescence element and material for organic electroluminescence element
US20140151647A1 (en) * 2011-12-05 2014-06-05 Yumiko Mizuki Material for organic electroluminescence device and organic electroluminescence device
WO2013146942A1 (en) * 2012-03-28 2013-10-03 出光興産株式会社 Novel compound, material for organic electroluminescence element, and organic electroluminescence element

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9947878B2 (en) 2014-08-20 2018-04-17 Lg Chem, Ltd. Organic light-emitting device
US11339132B2 (en) * 2016-01-21 2022-05-24 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
US11678498B2 (en) * 2016-04-07 2023-06-13 Samsung Display Co., Ltd. Organic light-emitting device
US20170294613A1 (en) * 2016-04-07 2017-10-12 Samsung Display Co., Ltd. Organic light-emitting device
US20170346022A1 (en) * 2016-05-25 2017-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US10840458B2 (en) * 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US11271165B2 (en) * 2016-07-14 2022-03-08 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element
US11751473B2 (en) 2016-07-26 2023-09-05 Lg Chem, Ltd. Organic light emitting element
US11205755B2 (en) * 2016-07-29 2021-12-21 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using same, and electronic device thereof
US20190013490A1 (en) * 2016-11-16 2019-01-10 Lg Chem, Ltd. Organic light emitting device
US11800730B2 (en) * 2016-11-16 2023-10-24 Lg Chem, Ltd. Organic light emitting device
US20180312514A1 (en) * 2017-05-01 2018-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) * 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US11702420B2 (en) 2017-05-01 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US20200343450A1 (en) * 2018-01-11 2020-10-29 Lg Chem, Ltd. Organic light-emitting diode
US11856843B2 (en) * 2018-03-29 2023-12-26 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and electronic device therefor
US20210028370A1 (en) * 2018-03-29 2021-01-28 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and electronic device therefor
US11482681B2 (en) 2018-07-27 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
EP3643761A1 (en) 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, organic electroluminescence device material, composition film, organic electroluminescence device, and electronic device
US11424417B2 (en) 2018-11-16 2022-08-23 Samsung Display Co., Ltd. Organic electroluminescence device and compound for organic electroluminescence device
US11462693B2 (en) * 2018-11-23 2022-10-04 Samsung Display Co., Ltd. Organic electroluminescence device
US12598909B2 (en) 2018-11-26 2026-04-07 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US20200190121A1 (en) * 2018-12-14 2020-06-18 Cynora Gmbh Organic electroluminescent devices comprising host compounds
US11512101B2 (en) * 2018-12-14 2022-11-29 Samsung Display Co., Ltd. Organic electroluminescent devices comprising host compounds
US12534665B2 (en) 2019-04-15 2026-01-27 Samsung Display Co., Ltd. Organometallic compound, organic light-emitting device including the same, and apparatus including the light-emitting device
US11985893B2 (en) 2019-11-08 2024-05-14 Samsung Display Co., Ltd. Organic electroluminescence device and aromatic compound for organic electroluminescence device
US20220367820A1 (en) * 2020-03-31 2022-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US12598906B2 (en) * 2020-03-31 2026-04-07 Universal Display Corporation Organic electroluminescent materials and devices
US12593606B2 (en) 2021-07-16 2026-03-31 Samsung Display Co., Ltd. Organic light-emitting device

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