WO2016076629A1 - A plurality of host materials and an organic electroluminescence device comprising the same - Google Patents

A plurality of host materials and an organic electroluminescence device comprising the same Download PDF

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Publication number
WO2016076629A1
WO2016076629A1 PCT/KR2015/012119 KR2015012119W WO2016076629A1 WO 2016076629 A1 WO2016076629 A1 WO 2016076629A1 KR 2015012119 W KR2015012119 W KR 2015012119W WO 2016076629 A1 WO2016076629 A1 WO 2016076629A1
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Prior art keywords
substituted
unsubstituted
independently represent
arylsilyl
aryl
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PCT/KR2015/012119
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French (fr)
Inventor
Jae-Hoon Shim
Kyoung-Jin Park
Yoo-Jin DOH
Bitnari Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150157677A external-priority patent/KR102593644B1/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN201580058272.XA priority Critical patent/CN107075363A/en
Priority to CN202210769424.9A priority patent/CN115132952A/en
Priority to US15/525,077 priority patent/US11130747B2/en
Publication of WO2016076629A1 publication Critical patent/WO2016076629A1/en

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Definitions

  • the present invention relates to a plurality of host materials 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.
  • the first organic EL device was 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 electrical 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, and 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 a long lifespan, ease of forming an 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 comprises plural host compounds, at least a first host compound of the plural 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
  • n an integer of 0 or 1;
  • n 1, a 5-membered ring including Z 1 is fused with the phenyl ring of carbazole;
  • a 5-membered ring including Z 2 is fused with the phenyl ring of carbazole;
  • L 1 and La each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;
  • Z 1 and Z 2 each independently represent CR 1 R 2 , NR 3 , O, or S;
  • X 1 to X 6 , and R 1 to R 3 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
  • Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl
  • 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 substituted or unsub
  • a and d each independently represent an integer of 1 to 2
  • b and e each independently represent an integer of 1 to 3
  • c and f each independently represent an integer of 1 to 4, where a, b, c, d, e, or f is an integer of 2 or more, each of X 1 , each of X 2 , each of X 3 , each of X 4 , each of X 5 , and each of X 6 may be the same or different;
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having high efficiency and long lifespan is provided, and a display device or a lighting device using the organic electroluminescent device can be manufactured.
  • the compound represented by formula 1 can be represented by one of the following formulas 3 to 6:
  • a 1 , A 2 , Z 1 , Z 2 , L 1 , X 1 to X 6 , and a to f 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, naphthylphenyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
  • X 1 to X 6 , and R 1 to R 3 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)ary
  • the compound represented by formula 1 can be preferably represented by one of the following formulas 7 to 36:
  • a 1 , A 2 , Z 1 , L 1 , X 1 to X 6 , and a to f are as defined in formula 1.
  • L 1 and La each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene; preferably each independently represent a single bond or a substituted or unsubstituted (C6-C12)arylene; and more preferably each independently represent a single bond, or a (C6-C12)arylene unsubstituted or substituted with a tri(C6-C10)arylsilyl or a (C6-C12)aryl.
  • L 1 and La may each independently represent a single bond, or one of the following formulas 37 to 49:
  • 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 unsub
  • Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl; preferably represents a substituted or unsubstituted 6- to 15-membered nitrogen-containing heteroaryl; and more preferably represents a 6- to 15-membered nitrogen-containing heteroaryl substituted with a substituent selected from the group consisting of 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, an unsubstituted 6- to 15-membered heteroaryl, and a 6- to 15-membered heteroaryl substituted with a (C6-C12)aryl.
  • a substituent selected from the group consisting of an unsubstituted (C6-C18)
  • Ma may represent a monocyclic ring-type heteroaryl such as a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, etc., or a fused ring-type heteroaryl such as a substituted or unsubstituted benzimidazolyl, a substituted or
  • Ma may represent a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted quinoxalinyl.
  • 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 substituted or unsub
  • Xa to Xh each independently represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with a 10- to 20-membered heteroaryl or 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 adjacent substituents may be linked to each other 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.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, 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 constituting the chain, 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
  • 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 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 material comprises plural host compounds, at least a first host compound of the plural 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 formulas 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 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 linked to each other
  • 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 a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 208 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
  • n 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 electrodes; 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.
  • 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 hole injection layer Between the anode and the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, or 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 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 3 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.
  • the two host materials were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host materials, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the hosts and dopant to evaporate and form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • Comparative Example 1-1 Preparation of an OLED device comprising only the first host compound of the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 1-1, except for using only the first host compound as a host of the light-emitting layer.
  • Comparative Example 1-2 Preparation of an OLED device comprising only the second host compound of the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 1-1, except for using only the second host compound as a host of the light-emitting layer.
  • a driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 97% of the luminance at 15,000 nit and a constant current of OLEDs are shown in Table 1 below.
  • An OLED device was produced in the same manner as in Device Example 1-1, except for evaporating the first hole transport layer of 40 nm thickness, not evaporating the second hole transport layer, using compound D-25 as a dopant of the light-emitting layer, and using the combination of the first host compound and the second host compound used as a host of the light-emitting layer as listed in Table 2 below.
  • Comparative Example 2-1 Preparation of an OLED device comprising only the second host compound of the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 2-1, except for using the second host compound as a host of the light-emitting material as listed in Table 2 below.
  • a driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 90% of the luminance at 15,000 nit and a constant current of OLEDs are shown in Table 2 below.
  • the organic electroluminescent device of the present invention comprises a light-emitting layer comprising a host and a phosphorus dopant.
  • the host consists of plural host compounds. At least a first host compound of the plural host compounds is a specific carbazole-(fused carbazole) derivative comprising an aryl, and a second host compound is a specific carbazole derivative comprising a nitrogen-containing heteroaryl.
  • the organic electroluminescent device of the present invention maintains a high luminous efficiency while having a longer lifespan than conventional devices.

Abstract

The present invention relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising a specific combination of a plurality of host compounds, the organic electroluminescent device according to the present invention provides high efficiency and long lifespan.

Description

A PLURALITY OF HOST MATERIALS AND AN ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE SAME
The present invention relates to a plurality of host materials and an organic electroluminescence device comprising the same.
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. The first organic EL device was 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 electrical 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 light-emitting materials. 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, and 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 a long lifespan, ease of forming an 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 No. WO 2013/168688 A1, Japanese Patent No. 3139321, Korean Patent No. 10-1170666, Korean Patent Application Laying-Open No. 10-2012-0013173, International Publication Nos. WO 2013/112557 A1 and WO 2009/060757 A1, and Japanese Patent Application Laying-Open No. 2013-183036 A disclose an organic electroluminescent device comprising a dopant/host material system, and use a compound of biscarbazole structure as a host. However, the aforementioned references fail to disclose an organic electroluminescent device using plural hosts comprising a biscarbazole compound fused with indene, indole, benzofuran, or benzothiophene, and a carbazole derivative comprising a nitrogen-containing heteroaryl.
The objective of the present invention is to provide an organic electroluminescent device having high efficiency and long lifespan.
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 comprises plural host compounds, at least a first host compound of the plural host compounds is represented by the following formula 1, and a second host compound is represented by the following formula 2:
Figure PCTKR2015012119-appb-I000001
Figure PCTKR2015012119-appb-I000002
wherein
A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl;
n represents an integer of 0 or 1;
where n is 1, a 5-membered ring including Z1 is fused with the phenyl ring of carbazole;
a 5-membered ring including Z2 is fused with the phenyl ring of carbazole;
L1 and La each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;
Z1 and Z2 each independently represent CR1R2, NR3, O, or S;
X1 to X6, and R1 to R3 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, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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;
Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl;
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 substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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;
a and d each independently represent an integer of 1 to 2, b and e each independently represent an integer of 1 to 3, c and f each independently represent an integer of 1 to 4, where a, b, c, d, e, or f is an integer of 2 or more, each of X1, each of X2, each of X3, each of X4, each of X5, and each of X6 may be the same or different; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
According to the present invention, an organic electroluminescent device having high efficiency and long lifespan is provided, and a display device or a lighting device using the organic electroluminescent device can be manufactured.
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.
The compound represented by formula 1 can be represented by one of the following formulas 3 to 6:
Figure PCTKR2015012119-appb-I000003
Figure PCTKR2015012119-appb-I000004
Figure PCTKR2015012119-appb-I000005
Figure PCTKR2015012119-appb-I000006
wherein
A1, A2, Z1, Z2, L1, X1 to X6, and a to f 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, naphthylphenyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
In formula 1 above, X1 to X6, and R1 to R3 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, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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 substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted tri(C6-C12)arylsilyl, or a substituted or unsubstituted 3- to 15-membered heteroaryl; and more preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, an unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran.
The compound represented by formula 1 can be preferably represented by one of the following formulas 7 to 36:
Figure PCTKR2015012119-appb-I000007
Figure PCTKR2015012119-appb-I000008
Figure PCTKR2015012119-appb-I000009
Figure PCTKR2015012119-appb-I000010
Figure PCTKR2015012119-appb-I000011
Figure PCTKR2015012119-appb-I000012
Figure PCTKR2015012119-appb-I000013
Figure PCTKR2015012119-appb-I000014
Figure PCTKR2015012119-appb-I000015
Figure PCTKR2015012119-appb-I000016
Figure PCTKR2015012119-appb-I000017
Figure PCTKR2015012119-appb-I000018
Figure PCTKR2015012119-appb-I000019
Figure PCTKR2015012119-appb-I000020
Figure PCTKR2015012119-appb-I000021
wherein
A1, A2, Z1, L1, X1 to X6, and a to f are as defined in formula 1.
In formulas 1 and 2 above, L1 and La each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene; preferably each independently represent a single bond or a substituted or unsubstituted (C6-C12)arylene; and more preferably each independently represent a single bond, or a (C6-C12)arylene unsubstituted or substituted with a tri(C6-C10)arylsilyl or a (C6-C12)aryl.
In addition, L1 and La may each independently represent a single bond, or one of the following formulas 37 to 49:
Figure PCTKR2015012119-appb-I000022
Figure PCTKR2015012119-appb-I000023
Figure PCTKR2015012119-appb-I000024
Figure PCTKR2015012119-appb-I000025
Figure PCTKR2015012119-appb-I000026
Figure PCTKR2015012119-appb-I000027
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, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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; and more preferably each independently represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsilyl, or a 10- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C15)aryl.
In formula 2 above, Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl; preferably represents a substituted or unsubstituted 6- to 15-membered nitrogen-containing heteroaryl; and more preferably represents a 6- to 15-membered nitrogen-containing heteroaryl substituted with a substituent selected from the group consisting of 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, an unsubstituted 6- to 15-membered heteroaryl, and a 6- to 15-membered heteroaryl substituted with a (C6-C12)aryl.
In addition, Ma may represent a monocyclic ring-type heteroaryl such as a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, etc., or a fused ring-type heteroaryl such as a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted phenanthridinyl, etc. Preferably, Ma may represent a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted quinoxalinyl.
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, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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 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 adjacent substituents may be linked to each other to form a substituted or unsubstituted mono- or polycyclic, (C6-C20) aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. More preferably, Xa to Xh each independently represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with a 10- to 20-membered heteroaryl or 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 adjacent substituents may be linked to each other 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(ene)” is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, 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 constituting the chain, 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 constituting the chain, 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 ring backbone 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, 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 ring backbone 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(ene)” is an aryl having 3 to 30 ring backbone atoms, preferably 3 to 20 ring backbone atoms, and more preferably 3 to 15 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, 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, benzimidazolyl, 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(ene)” 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 benzimidazolyl, 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(ene), 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- alkylamino, the substituted mono- or di- arylamino, or the substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring in the formulas 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.
The first host compound represented by formula 1 includes the following compounds, but is not limited thereto:
Figure PCTKR2015012119-appb-I000028
Figure PCTKR2015012119-appb-I000029
Figure PCTKR2015012119-appb-I000030
Figure PCTKR2015012119-appb-I000031
Figure PCTKR2015012119-appb-I000032
Figure PCTKR2015012119-appb-I000033
Figure PCTKR2015012119-appb-I000034
Figure PCTKR2015012119-appb-I000035
Figure PCTKR2015012119-appb-I000036
Figure PCTKR2015012119-appb-I000037
Figure PCTKR2015012119-appb-I000038
Figure PCTKR2015012119-appb-I000039
Figure PCTKR2015012119-appb-I000040
Figure PCTKR2015012119-appb-I000041
Figure PCTKR2015012119-appb-I000042
Figure PCTKR2015012119-appb-I000043
Figure PCTKR2015012119-appb-I000044
Figure PCTKR2015012119-appb-I000045
Figure PCTKR2015012119-appb-I000046
Figure PCTKR2015012119-appb-I000047
Figure PCTKR2015012119-appb-I000048
Figure PCTKR2015012119-appb-I000049
Figure PCTKR2015012119-appb-I000050
Figure PCTKR2015012119-appb-I000051
Figure PCTKR2015012119-appb-I000052
Figure PCTKR2015012119-appb-I000053
Figure PCTKR2015012119-appb-I000054
Figure PCTKR2015012119-appb-I000055
Figure PCTKR2015012119-appb-I000056
Figure PCTKR2015012119-appb-I000057
Figure PCTKR2015012119-appb-I000058
Figure PCTKR2015012119-appb-I000059
Figure PCTKR2015012119-appb-I000060
Figure PCTKR2015012119-appb-I000061
Figure PCTKR2015012119-appb-I000062
Figure PCTKR2015012119-appb-I000063
Figure PCTKR2015012119-appb-I000064
Figure PCTKR2015012119-appb-I000065
Figure PCTKR2015012119-appb-I000066
Figure PCTKR2015012119-appb-I000067
Figure PCTKR2015012119-appb-I000068
Figure PCTKR2015012119-appb-I000069
Figure PCTKR2015012119-appb-I000070
Figure PCTKR2015012119-appb-I000071
Figure PCTKR2015012119-appb-I000072
Figure PCTKR2015012119-appb-I000073
Figure PCTKR2015012119-appb-I000074
Figure PCTKR2015012119-appb-I000075
Figure PCTKR2015012119-appb-I000076
Figure PCTKR2015012119-appb-I000077
Figure PCTKR2015012119-appb-I000078
Figure PCTKR2015012119-appb-I000079
Figure PCTKR2015012119-appb-I000080
Figure PCTKR2015012119-appb-I000081
Figure PCTKR2015012119-appb-I000082
Figure PCTKR2015012119-appb-I000083
Figure PCTKR2015012119-appb-I000084
Figure PCTKR2015012119-appb-I000085
Figure PCTKR2015012119-appb-I000086
Figure PCTKR2015012119-appb-I000087
Figure PCTKR2015012119-appb-I000088
Figure PCTKR2015012119-appb-I000089
Figure PCTKR2015012119-appb-I000090
Figure PCTKR2015012119-appb-I000091
Figure PCTKR2015012119-appb-I000092
Figure PCTKR2015012119-appb-I000093
Figure PCTKR2015012119-appb-I000094
Figure PCTKR2015012119-appb-I000095
Figure PCTKR2015012119-appb-I000096
Figure PCTKR2015012119-appb-I000097
Figure PCTKR2015012119-appb-I000098
Figure PCTKR2015012119-appb-I000099
Figure PCTKR2015012119-appb-I000100
Figure PCTKR2015012119-appb-I000101
Figure PCTKR2015012119-appb-I000102
Figure PCTKR2015012119-appb-I000103
Figure PCTKR2015012119-appb-I000104
Figure PCTKR2015012119-appb-I000105
Figure PCTKR2015012119-appb-I000106
Figure PCTKR2015012119-appb-I000107
Figure PCTKR2015012119-appb-I000108
Figure PCTKR2015012119-appb-I000109
Figure PCTKR2015012119-appb-I000110
Figure PCTKR2015012119-appb-I000111
Figure PCTKR2015012119-appb-I000112
Figure PCTKR2015012119-appb-I000113
Figure PCTKR2015012119-appb-I000114
Figure PCTKR2015012119-appb-I000115
Figure PCTKR2015012119-appb-I000116
Figure PCTKR2015012119-appb-I000117
Figure PCTKR2015012119-appb-I000118
Figure PCTKR2015012119-appb-I000119
Figure PCTKR2015012119-appb-I000120
Figure PCTKR2015012119-appb-I000121
Figure PCTKR2015012119-appb-I000122
Figure PCTKR2015012119-appb-I000123
Figure PCTKR2015012119-appb-I000124
Figure PCTKR2015012119-appb-I000125
Figure PCTKR2015012119-appb-I000126
Figure PCTKR2015012119-appb-I000127
Figure PCTKR2015012119-appb-I000128
Figure PCTKR2015012119-appb-I000129
Figure PCTKR2015012119-appb-I000130
The second host compound represented by formula 2 includes the following compounds, but is not limited thereto:
Figure PCTKR2015012119-appb-I000131
Figure PCTKR2015012119-appb-I000132
Figure PCTKR2015012119-appb-I000133
Figure PCTKR2015012119-appb-I000134
Figure PCTKR2015012119-appb-I000135
Figure PCTKR2015012119-appb-I000136
Figure PCTKR2015012119-appb-I000137
Figure PCTKR2015012119-appb-I000138
Figure PCTKR2015012119-appb-I000139
Figure PCTKR2015012119-appb-I000140
Figure PCTKR2015012119-appb-I000141
Figure PCTKR2015012119-appb-I000142
Figure PCTKR2015012119-appb-I000143
Figure PCTKR2015012119-appb-I000144
Figure PCTKR2015012119-appb-I000145
Figure PCTKR2015012119-appb-I000146
Figure PCTKR2015012119-appb-I000147
Figure PCTKR2015012119-appb-I000148
Figure PCTKR2015012119-appb-I000149
Figure PCTKR2015012119-appb-I000150
Figure PCTKR2015012119-appb-I000151
Figure PCTKR2015012119-appb-I000152
Figure PCTKR2015012119-appb-I000153
Figure PCTKR2015012119-appb-I000154
Figure PCTKR2015012119-appb-I000155
Figure PCTKR2015012119-appb-I000156
Figure PCTKR2015012119-appb-I000157
Figure PCTKR2015012119-appb-I000158
Figure PCTKR2015012119-appb-I000159
Figure PCTKR2015012119-appb-I000160
Figure PCTKR2015012119-appb-I000161
Figure PCTKR2015012119-appb-I000162
Figure PCTKR2015012119-appb-I000163
Figure PCTKR2015012119-appb-I000164
Figure PCTKR2015012119-appb-I000165
Figure PCTKR2015012119-appb-I000166
Figure PCTKR2015012119-appb-I000167
Figure PCTKR2015012119-appb-I000168
Figure PCTKR2015012119-appb-I000169
Figure PCTKR2015012119-appb-I000170
Figure PCTKR2015012119-appb-I000171
Figure PCTKR2015012119-appb-I000172
Figure PCTKR2015012119-appb-I000173
Figure PCTKR2015012119-appb-I000174
Figure PCTKR2015012119-appb-I000175
Figure PCTKR2015012119-appb-I000176
Figure PCTKR2015012119-appb-I000177
Figure PCTKR2015012119-appb-I000178
Figure PCTKR2015012119-appb-I000179
Figure PCTKR2015012119-appb-I000180
Figure PCTKR2015012119-appb-I000181
Figure PCTKR2015012119-appb-I000183
Figure PCTKR2015012119-appb-I000184
Figure PCTKR2015012119-appb-I000185
Figure PCTKR2015012119-appb-I000186
Figure PCTKR2015012119-appb-I000187
Figure PCTKR2015012119-appb-I000188
Figure PCTKR2015012119-appb-I000189
Figure PCTKR2015012119-appb-I000190
Figure PCTKR2015012119-appb-I000191
Figure PCTKR2015012119-appb-I000192
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 material comprises plural host compounds, at least a first host compound of the plural 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 formulas 101 to 103.
Figure PCTKR2015012119-appb-I000193
Figure PCTKR2015012119-appb-I000194
Figure PCTKR2015012119-appb-I000195
wherein L is selected from the following structures:
Figure PCTKR2015012119-appb-I000196
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 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 a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R208 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
m represents an integer of 1 to 3.
Specifically, the phosphorescent dopant materials include the following:
Figure PCTKR2015012119-appb-I000197
Figure PCTKR2015012119-appb-I000198
Figure PCTKR2015012119-appb-I000199
Figure PCTKR2015012119-appb-I000200
Figure PCTKR2015012119-appb-I000201
Figure PCTKR2015012119-appb-I000202
Figure PCTKR2015012119-appb-I000203
Figure PCTKR2015012119-appb-I000204
Figure PCTKR2015012119-appb-I000205
Figure PCTKR2015012119-appb-I000206
Figure PCTKR2015012119-appb-I000207
Figure PCTKR2015012119-appb-I000208
Figure PCTKR2015012119-appb-I000209
Figure PCTKR2015012119-appb-I000210
Figure PCTKR2015012119-appb-I000211
Figure PCTKR2015012119-appb-I000212
Figure PCTKR2015012119-appb-I000213
Figure PCTKR2015012119-appb-I000214
Figure PCTKR2015012119-appb-I000215
Figure PCTKR2015012119-appb-I000216
Figure PCTKR2015012119-appb-I000217
Figure PCTKR2015012119-appb-I000218
Figure PCTKR2015012119-appb-I000219
Figure PCTKR2015012119-appb-I000220
Figure PCTKR2015012119-appb-I000221
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 electrodes; 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 hole injection layer, a hole transport layer, an electron blocking layer, or 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 1-2: Preparation of an OLED device wherein the first host compound and the second host compound of the present invention are
co-evaporated
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 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 3 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-([1,1'-biphenyl]-4-yl)-N-(4-(9-(dibenzo[b,d]furan-4-yl)-9H-fluoren-9-yl)phenyl)-[1,1'-bilhenyl]-4-amine (compound HT-2) 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 second hole transport layer having a thickness of 30 nm on the first hole transport layer. Compound F-13 or F-31 and compound H2-125 were introduced into two cells of said vacuum vapor depositing apparatus as hosts, and compound D-136 was introduced into another cell as a dopant. The two host materials were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host materials, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the hosts and dopant to evaporate and form a light-emitting layer having a thickness of 40 nm on the second 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 a rate of 4:6 to form an electron transport layer having a thickness of 35 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. All the materials used for producing the OLED device were those purified by vacuum sublimation at 10-6 torr.
Figure PCTKR2015012119-appb-I000222
Comparative Example 1-1: Preparation of an OLED device comprising only the first host compound of the present invention as a host
An OLED device was produced in the same manner as in Device Example 1-1, except for using only the first host compound as a host of the light-emitting layer.
Comparative Example 1-2: Preparation of an OLED device comprising only the second host compound of the present invention as a host
An OLED device was produced in the same manner as in Device Example 1-1, except for using only the second host compound as a host of the light-emitting layer.
A driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 97% of the luminance at 15,000 nit and a constant current of OLEDs are shown in Table 1 below.
Figure PCTKR2015012119-appb-I000223
Device Examples 2-1 to 2-3: Preparation of an OLED device wherein the first host compound and the second host compound of the present invention are
co-evaporated
An OLED device was produced in the same manner as in Device Example 1-1, except for evaporating the first hole transport layer of 40 nm thickness, not evaporating the second hole transport layer, using compound D-25 as a dopant of the light-emitting layer, and using the combination of the first host compound and the second host compound used as a host of the light-emitting layer as listed in Table 2 below.
Comparative Example 2-1: Preparation of an OLED device comprising only the second host compound of the present invention as a host
An OLED device was produced in the same manner as in Device Example 2-1, except for using the second host compound as a host of the light-emitting material as listed in Table 2 below.
A driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 90% of the luminance at 15,000 nit and a constant current of OLEDs are shown in Table 2 below.
Figure PCTKR2015012119-appb-I000224
The organic electroluminescent device of the present invention comprises a light-emitting layer comprising a host and a phosphorus dopant. The host consists of plural host compounds. At least a first host compound of the plural host compounds is a specific carbazole-(fused carbazole) derivative comprising an aryl, and a second host compound is a specific carbazole derivative comprising a nitrogen-containing heteroaryl. The organic electroluminescent device of the present invention maintains a high luminous efficiency while having a longer lifespan than conventional devices.

Claims (10)

  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 comprises plural host compounds; at least a first host compound of the plural host compounds is represented by the following formula 1; and a second host compound is represented by the following formula 2.
    Figure PCTKR2015012119-appb-I000225
    Figure PCTKR2015012119-appb-I000226
    wherein
    A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl;
    n represents an integer of 0 or 1;
    where n is 1, a 5-membered ring including Z1 is fused with the phenyl ring of carbazole;
    a 5-membered ring including Z2 is fused with the phenyl ring of carbazole;
    L1 and La each independently represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;
    Z1 and Z2 each independently represent CR1R2, NR3, O, or S;
    X1 to X6, and R1 to R3 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, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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;
    Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl;
    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 substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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;
    a and d each independently represent an integer of 1 to 2, b and e each independently represent an integer of 1 to 3, c and f each independently represent an integer of 1 to 4, where a, b, c, d, e, or f is an integer of 2 or more, each of X1, each of X2, each of X3, each of X4, each of X5, and each of X6 may be the same or different; and
    the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  2. The organic electroluminescent device according to claim 1, wherein formula 1 is represented by one of the following formulas 3 to 6:
    Figure PCTKR2015012119-appb-I000227
    Figure PCTKR2015012119-appb-I000228
    Figure PCTKR2015012119-appb-I000229
    Figure PCTKR2015012119-appb-I000230
    wherein
    A1, A2, Z1, Z2, L1, X1 to X6, and a to f are as defined in claim 1.
  3. The organic electroluminescent device according to claim 1, wherein formula 1 is represented by one of the following formulas 7 to 36:
    Figure PCTKR2015012119-appb-I000231
    Figure PCTKR2015012119-appb-I000232
    Figure PCTKR2015012119-appb-I000233
    Figure PCTKR2015012119-appb-I000234
    Figure PCTKR2015012119-appb-I000235
    Figure PCTKR2015012119-appb-I000236
    Figure PCTKR2015012119-appb-I000237
    Figure PCTKR2015012119-appb-I000238
    Figure PCTKR2015012119-appb-I000239
    Figure PCTKR2015012119-appb-I000240
    Figure PCTKR2015012119-appb-I000241
    Figure PCTKR2015012119-appb-I000242
    Figure PCTKR2015012119-appb-I000243
    Figure PCTKR2015012119-appb-I000244
    Figure PCTKR2015012119-appb-I000245
    wherein
    A1, A2, Z1, L1, X1 to X6, and a to f are as defined in claim 1.
  4. The organic electroluminescent device according to claim 1, wherein in formulas 1 and 2,
    L1 and La each independently represent a single bond, or one of the following formulas 37 to 49:
    Figure PCTKR2015012119-appb-I000246
    Figure PCTKR2015012119-appb-I000247
    Figure PCTKR2015012119-appb-I000248
    Figure PCTKR2015012119-appb-I000249
    Figure PCTKR2015012119-appb-I000250
    Figure PCTKR2015012119-appb-I000251
    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, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or adjacent substituents may be linked to each other 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.
  5. The organic electroluminescent device according to claim 1, wherein in formula 1,
    A1 and A2 each independently represent phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
  6. The organic electroluminescent device according to claim 1, wherein in formula 1,
    X1 to X6, and R1 to R3 each independently represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, an unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran.
  7. The organic electroluminescent device according to claim 1, wherein in formula 2,
    Ma represents a monocyclic ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, and a substituted or unsubstituted pyridazinyl, or a fused ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted carbazolyl, and a substituted or unsubstituted phenanthridinyl.
  8. 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 10- to 20-membered heteroaryl or 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 adjacent substituents may be linked to each other 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.
  9. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2015012119-appb-I000252
    Figure PCTKR2015012119-appb-I000253
    Figure PCTKR2015012119-appb-I000254
    Figure PCTKR2015012119-appb-I000255
    Figure PCTKR2015012119-appb-I000256
    Figure PCTKR2015012119-appb-I000257
    Figure PCTKR2015012119-appb-I000258
    Figure PCTKR2015012119-appb-I000259
    Figure PCTKR2015012119-appb-I000260
    Figure PCTKR2015012119-appb-I000261
    Figure PCTKR2015012119-appb-I000262
    Figure PCTKR2015012119-appb-I000263
    Figure PCTKR2015012119-appb-I000264
    Figure PCTKR2015012119-appb-I000265
    Figure PCTKR2015012119-appb-I000266
    Figure PCTKR2015012119-appb-I000267
    Figure PCTKR2015012119-appb-I000268
    Figure PCTKR2015012119-appb-I000269
    Figure PCTKR2015012119-appb-I000270
    Figure PCTKR2015012119-appb-I000271
    Figure PCTKR2015012119-appb-I000272
    Figure PCTKR2015012119-appb-I000273
    Figure PCTKR2015012119-appb-I000274
    Figure PCTKR2015012119-appb-I000275
    Figure PCTKR2015012119-appb-I000276
    Figure PCTKR2015012119-appb-I000277
    Figure PCTKR2015012119-appb-I000278
    Figure PCTKR2015012119-appb-I000279
    Figure PCTKR2015012119-appb-I000280
    Figure PCTKR2015012119-appb-I000281
    Figure PCTKR2015012119-appb-I000282
    Figure PCTKR2015012119-appb-I000283
    Figure PCTKR2015012119-appb-I000284
    Figure PCTKR2015012119-appb-I000285
    Figure PCTKR2015012119-appb-I000286
    Figure PCTKR2015012119-appb-I000287
    Figure PCTKR2015012119-appb-I000288
    Figure PCTKR2015012119-appb-I000289
    Figure PCTKR2015012119-appb-I000290
    Figure PCTKR2015012119-appb-I000291
    Figure PCTKR2015012119-appb-I000292
    Figure PCTKR2015012119-appb-I000293
    Figure PCTKR2015012119-appb-I000294
    Figure PCTKR2015012119-appb-I000295
    Figure PCTKR2015012119-appb-I000296
    Figure PCTKR2015012119-appb-I000297
    Figure PCTKR2015012119-appb-I000298
    Figure PCTKR2015012119-appb-I000299
    Figure PCTKR2015012119-appb-I000300
    Figure PCTKR2015012119-appb-I000301
    Figure PCTKR2015012119-appb-I000302
    Figure PCTKR2015012119-appb-I000303
    Figure PCTKR2015012119-appb-I000304
    Figure PCTKR2015012119-appb-I000305
    Figure PCTKR2015012119-appb-I000306
    Figure PCTKR2015012119-appb-I000307
    Figure PCTKR2015012119-appb-I000308
    Figure PCTKR2015012119-appb-I000309
    Figure PCTKR2015012119-appb-I000310
    Figure PCTKR2015012119-appb-I000311
    Figure PCTKR2015012119-appb-I000312
    Figure PCTKR2015012119-appb-I000313
    Figure PCTKR2015012119-appb-I000314
    Figure PCTKR2015012119-appb-I000315
    Figure PCTKR2015012119-appb-I000316
    Figure PCTKR2015012119-appb-I000317
    Figure PCTKR2015012119-appb-I000318
    Figure PCTKR2015012119-appb-I000319
    Figure PCTKR2015012119-appb-I000320
    Figure PCTKR2015012119-appb-I000321
    Figure PCTKR2015012119-appb-I000322
    Figure PCTKR2015012119-appb-I000323
    Figure PCTKR2015012119-appb-I000324
    Figure PCTKR2015012119-appb-I000325
    Figure PCTKR2015012119-appb-I000326
    Figure PCTKR2015012119-appb-I000327
    Figure PCTKR2015012119-appb-I000328
    Figure PCTKR2015012119-appb-I000329
    Figure PCTKR2015012119-appb-I000330
    Figure PCTKR2015012119-appb-I000331
    Figure PCTKR2015012119-appb-I000332
    Figure PCTKR2015012119-appb-I000333
    Figure PCTKR2015012119-appb-I000334
    Figure PCTKR2015012119-appb-I000335
    Figure PCTKR2015012119-appb-I000336
    Figure PCTKR2015012119-appb-I000337
    Figure PCTKR2015012119-appb-I000338
    Figure PCTKR2015012119-appb-I000339
    Figure PCTKR2015012119-appb-I000340
    Figure PCTKR2015012119-appb-I000341
    Figure PCTKR2015012119-appb-I000342
    Figure PCTKR2015012119-appb-I000343
    Figure PCTKR2015012119-appb-I000344
    Figure PCTKR2015012119-appb-I000345
    Figure PCTKR2015012119-appb-I000346
    Figure PCTKR2015012119-appb-I000347
    Figure PCTKR2015012119-appb-I000348
    Figure PCTKR2015012119-appb-I000349
    Figure PCTKR2015012119-appb-I000350
    Figure PCTKR2015012119-appb-I000351
    Figure PCTKR2015012119-appb-I000352
    Figure PCTKR2015012119-appb-I000353
    Figure PCTKR2015012119-appb-I000354
  10. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
    Figure PCTKR2015012119-appb-I000355
    Figure PCTKR2015012119-appb-I000356
    Figure PCTKR2015012119-appb-I000357
    Figure PCTKR2015012119-appb-I000358
    Figure PCTKR2015012119-appb-I000359
    Figure PCTKR2015012119-appb-I000360
    Figure PCTKR2015012119-appb-I000361
    Figure PCTKR2015012119-appb-I000362
    Figure PCTKR2015012119-appb-I000363
    Figure PCTKR2015012119-appb-I000364
    Figure PCTKR2015012119-appb-I000365
    Figure PCTKR2015012119-appb-I000366
    Figure PCTKR2015012119-appb-I000367
    Figure PCTKR2015012119-appb-I000368
    Figure PCTKR2015012119-appb-I000369
    Figure PCTKR2015012119-appb-I000370
    Figure PCTKR2015012119-appb-I000371
    Figure PCTKR2015012119-appb-I000372
    Figure PCTKR2015012119-appb-I000373
    Figure PCTKR2015012119-appb-I000374
    Figure PCTKR2015012119-appb-I000375
    Figure PCTKR2015012119-appb-I000376
    Figure PCTKR2015012119-appb-I000377
    Figure PCTKR2015012119-appb-I000378
    Figure PCTKR2015012119-appb-I000379
    Figure PCTKR2015012119-appb-I000380
    Figure PCTKR2015012119-appb-I000381
    Figure PCTKR2015012119-appb-I000382
    Figure PCTKR2015012119-appb-I000383
    Figure PCTKR2015012119-appb-I000384
    Figure PCTKR2015012119-appb-I000385
    Figure PCTKR2015012119-appb-I000386
    Figure PCTKR2015012119-appb-I000387
    Figure PCTKR2015012119-appb-I000388
    Figure PCTKR2015012119-appb-I000389
    Figure PCTKR2015012119-appb-I000390
    Figure PCTKR2015012119-appb-I000391
    Figure PCTKR2015012119-appb-I000392
    Figure PCTKR2015012119-appb-I000393
    Figure PCTKR2015012119-appb-I000394
    Figure PCTKR2015012119-appb-I000395
    Figure PCTKR2015012119-appb-I000396
    Figure PCTKR2015012119-appb-I000397
    Figure PCTKR2015012119-appb-I000398
    Figure PCTKR2015012119-appb-I000399
    Figure PCTKR2015012119-appb-I000400
    Figure PCTKR2015012119-appb-I000401
    Figure PCTKR2015012119-appb-I000402
    Figure PCTKR2015012119-appb-I000403
    Figure PCTKR2015012119-appb-I000404
    Figure PCTKR2015012119-appb-I000405
    Figure PCTKR2015012119-appb-I000406
    Figure PCTKR2015012119-appb-I000407
    Figure PCTKR2015012119-appb-I000408
    Figure PCTKR2015012119-appb-I000409
    Figure PCTKR2015012119-appb-I000410
    Figure PCTKR2015012119-appb-I000411
    Figure PCTKR2015012119-appb-I000412
    Figure PCTKR2015012119-appb-I000413
    Figure PCTKR2015012119-appb-I000414
    Figure PCTKR2015012119-appb-I000415
    Figure PCTKR2015012119-appb-I000416
PCT/KR2015/012119 2014-11-11 2015-11-11 A plurality of host materials and an organic electroluminescence device comprising the same WO2016076629A1 (en)

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US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
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