WO2016080791A1 - A plurality of host materials and an organic electroluminescent device comprising the same - Google Patents

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

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WO2016080791A1
WO2016080791A1 PCT/KR2015/012494 KR2015012494W WO2016080791A1 WO 2016080791 A1 WO2016080791 A1 WO 2016080791A1 KR 2015012494 W KR2015012494 W KR 2015012494W WO 2016080791 A1 WO2016080791 A1 WO 2016080791A1
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substituted
unsubstituted
group
host
organic electroluminescent
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PCT/KR2015/012494
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French (fr)
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Jae-Hoon Shim
Hee-Ryong Kang
Ji-Song JUN
Kyoung-Jin Park
Bitnari Kim
Yoo-Jin DOH
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150161906A external-priority patent/KR20160060569A/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Publication of WO2016080791A1 publication Critical patent/WO2016080791A1/en

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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Definitions

  • the present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
  • An electroluminescent (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 to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • OLED organic electroluminescent device
  • electricity is applied to an organic light-emitting material which converts electric energy to light.
  • OLED has a structure comprising an anode, a cathode, and an organic layer disposed between the two electrodes.
  • the organic layer of OLED may comprise a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host and dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • a material for preparing the organic layer can be classified according to its function, as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • Holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer by applying electricity to OLED; excitons having high energy are formed by recombinations between the holes and the electrons, which make organic light-emitting compounds be in an excited state, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in OLED is a light-emitting material.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable. According to colors visualized by light-emission, the light-emitting material can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Furthermore, the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of OLED providing high efficiency and long lifespan is urgent.
  • a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under vacuum.
  • a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to have long lifespan; ease of preparation for amorphous thin film; and good adhesion to materials of adjacent layers.
  • a host material should not move to an adjacent layer.
  • the light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability.
  • a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant.
  • the host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
  • Japanese Patent Application Laid-open No. 2014-160813 A2 discloses an organic electroluminescent device comprising a nitrogen-containing heteroaryl compound formed by condensing a pyrrole ring, an aromatic aryl ring, and 7-membered aryl ring as a host/dopant material. Also, an organic electroluminescent device using only a sole host material is disclosed in the Example. However, the above publication does not specifically disclose an organic electroluminescent device using a plurality of host materials comprising specific nitrogen-containing heteroaryl derivatives, and specific carbazole derivatives linked with a nitrogen-containing heteroaryl directly or via an arylene group.
  • the present inventors have tried to find an organic electroluminescent device that can provide superior efficiency and long lifespan, and have found that it could be using a plurality of host materials comprising specific nitrogen-containing heteroaryl derivatives, and specific carbazole derivatives linked with a nitrogen-containing heteroaryl directly or via arylene group compared to using the conventional sole host material.
  • the objective of the present disclosure is to provide an organic electroluminescent device having long lifespan while maintaining high luminous efficiency.
  • an organic electroluminescent device comprising at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host comprises a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
  • a second host compound is represented by the following formula 2:
  • Ar 1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl group
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group
  • R 1 to R 8 and R 11 to R 18 each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group,
  • the heteroaryl group 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.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
  • the organic electroluminescent device comprising the compound of formula 1 and the compound of formula 2 will be described in detail.
  • R 1 to R 8 each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsub
  • R 1 to R 8 in formula 1, each independently, may be selected from the group consisting of:
  • L represents a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (5- to 20-membered)heteroarylene group; preferably, an unsubstituted (C6-C18)arylene group; more preferably, an unsubstituted (C6-C10)arylene group; and for example, phenylene;
  • n represents an integer of 0 to 2; and preferably, 0 or 1;
  • R 21 to R 25 and R 31 each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted
  • the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P, and preferably, at least one hetero atom selected from N, O and S.
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene group; more preferably, a single bond, or (C6-C12)arylene group which is unsubstituted or substituted with tri(C6-C10)arylsilyl group; and for example, a single bond, phenylene unsubstituted or substituted with triphenylsilyl, naphthylene, or biphenylene.
  • L 1 may be represented by any one of the following formulae 7 to 19:
  • Xi to Xp each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30
  • Ar 1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl group; preferably, a substituted or unsubstituted nitrogen-containing (5- to 11- membered)heteroayl group; more preferably, a nitrogen-containing (5- to 11- membered)heteroayl group unsubstituted or substituted with the substituent selected from the group consisting of (C6-C18) aryl group which is unsubstituted or substituted with a cyano group, (C1-C6) alkyl group, or tri(C6-C12)arylsilyl; and a (6- to 15- membered) heteroaryl group.
  • Ar 1 in formula 2 may be a monocyclic ring-type heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, or a fused ring-type heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl and phenanthridinyl; and preferably, triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quina
  • R 11 to R 18 in formula 2 each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a
  • (C1-C30)alkyl 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
  • halogen includes F, Cl, Br, and I.
  • 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 of formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
  • the second host compound of formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto:
  • the organic electroluminescent device of the present disclosure comprises an anode; a cathode; and at least one organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; the light-emitting layer comprises a host and a phosphorescent dopant; the host comprises a plurality of host compounds; and at least a first host compound of a plurality of host compounds is represented by formula 1, and a second host compound is represented by formula 2.
  • the light-emitting layer indicates a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopant may be selected from the group consisting of compounds represented by the following formulae 101 to 103.
  • La is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
  • R 101 to R 109 and R 111 to R1 23 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
  • R 106 to R 109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • R 120 to R 123
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R 124 to R 127 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R 208 to R 211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • r and s each independently represent an integer of 1 to 3; when 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 material includes the following:
  • the organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds at 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • a surface layer may be 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 (includes 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.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer.
  • the hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds.
  • the hole transport layer or electron blocking layer may be composed of two or more layers.
  • An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode.
  • the electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer.
  • Each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may 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 may be 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
  • 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 light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • 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.
  • the first host compound and the second host compound may be film-formed by co-evaporaton or mixture-evaporaton.
  • 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 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 electric current to the cell for the mixture to be evaporated.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
  • An OLED device was produced using the light-emitting material of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then 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 the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-1 , 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 then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying 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 introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • a compound D-1 was introduced into another cell as a dopant.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 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.
  • first host compound as a sole host
  • An OLED device was produced in the same manner as in Device Example 1-1, except that only a first host compound of K-1 was used as a host for a light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 1-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
  • the driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 90% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 1-1, and Comparative Examples 1-1 and 1-2 are shown in Table 1 below.
  • An OLED device was produced in the same manner as in Device Example 1-1, except that compound D-25 was used as a dopant.
  • An OLED device was produced in the same manner as in Device Example 2-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
  • the driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 97% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 2-1 and Comparative Example 2-1 are shown in Table 2 below.
  • An OLED device was produced in the same manner as in Device Example 1-1, except that compound D-136 was used as a dopant.
  • An OLED device was produced in the same manner as in Device Example 3-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
  • the driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 95% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 3-1 and Comparative Example 3-1 are shown in Table 3 below.
  • An OLED device was produced using the light-emitting material of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-2 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • a first host compound and a second host compound of Device Examples 4-1 to 4-4 shown in Table 4 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • Compound D-125 was introduced into another cell as a dopant.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 12 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • compound ET-2 was deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED device was produced.
  • OLED device was produced in the same manner as in Device Examples 4-1 to 4-4, except that only a host compound of Comparative Examples 4-1 and 4-2 shown in Table 4 was used as a sole host for a light-emitting layer.
  • the driving voltage, a luminous efficiency and a CIE color coordinate based on 10 mA/cm 2 of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 97% based on a luminance of 10,000 nits of the organic electroluminescent devices produced in Device Examples 4-1 to 4-4 and Comparative Examples 4-1 and 4-2 are shown in Table 4 below.
  • An OLED device was produced in the same manner as in Device Example 1-1, except that the second hole injection layer was deposited as a thickness of 5 nm, compound HT-3 was deposited as the second hole transport layer having a thickness of 60 nm, a first host compound and a second host compound of Device Examples 5-1 and 5-2 shown in Table 5 were used, compound D-96 was deposited in a doping amount of 3 wt% as a dopant, and the electron transport layer was deposited as a thickness of 30 nm at the rate of 1:1.
  • An OLED device was produced in the same manner as in Device Example 5-1, except that only a second host compound of H2-41 was used as a host for a light-emitting layer.
  • the driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 98% based on a luminance of 5,000 nits of the organic electroluminescent devices produced in Device Examples 5-1 and 5-2, and Comparative Example 5-1 are shown in Table 5 below.
  • the present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
  • a plurality of host materials of the present disclosure it is possible to produce an organic electroluminescent device having excellent current efficiency and power efficiency and improved driving lifespan compared to conventional devices using only a sole host.

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Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By using a specific combination of a plurality of host materials of the present disclosure, it is possible to produce an organic electroluminescent device having improved driving lifespan and excellent current efficiency and power efficiency compared to the organic electroluminescent device using the conventional sole host material.

Description

A PLURALITY OF HOST MATERIALS AND AN ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
An electroluminescent (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 to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
In an organic electroluminescent device (OLED), electricity is applied to an organic light-emitting material which converts electric energy to light. Generally, OLED has a structure comprising an anode, a cathode, and an organic layer disposed between the two electrodes. The organic layer of OLED may comprise a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host and dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. A material for preparing the organic layer can be classified according to its function, as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc. Holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer by applying electricity to OLED; excitons having high energy are formed by recombinations between the holes and the electrons, which make organic light-emitting compounds be in an excited state, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in OLED is a light-emitting material. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. According to colors visualized by light-emission, the light-emitting material can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Furthermore, the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of OLED providing high efficiency and long lifespan is urgent. In particular, considering EL requirements for a middle or large-sized OLED panel, materials showing better performances than conventional ones must be urgently developed. In order to achieve the development, a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under vacuum. In addition, a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to have long lifespan; ease of preparation for amorphous thin film; and good adhesion to materials of adjacent layers. Furthermore, a host material should not move to an adjacent layer.
The light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability. Generally, a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant. The host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
Japanese Patent Application Laid-open No. 2014-160813 A2 discloses an organic electroluminescent device comprising a nitrogen-containing heteroaryl compound formed by condensing a pyrrole ring, an aromatic aryl ring, and 7-membered aryl ring as a host/dopant material. Also, an organic electroluminescent device using only a sole host material is disclosed in the Example. However, the above publication does not specifically disclose an organic electroluminescent device using a plurality of host materials comprising specific nitrogen-containing heteroaryl derivatives, and specific carbazole derivatives linked with a nitrogen-containing heteroaryl directly or via an arylene group.
In this regard, the present inventors have tried to find an organic electroluminescent device that can provide superior efficiency and long lifespan, and have found that it could be using a plurality of host materials comprising specific nitrogen-containing heteroaryl derivatives, and specific carbazole derivatives linked with a nitrogen-containing heteroaryl directly or via arylene group compared to using the conventional sole host material.
The objective of the present disclosure is to provide an organic electroluminescent device having long lifespan while maintaining high luminous efficiency.
The present inventors found that the above objective can be achieved by an organic electroluminescent device comprising at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host comprises a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
Figure PCTKR2015012494-appb-I000001
and
a second host compound is represented by the following formula 2:
Figure PCTKR2015012494-appb-I000002
wherein
Ar1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl group;
L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
R1 to R8 and R11 to R18, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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 group contains at least one hetero atom selected from B, N, O, S, Si, and P.
According to the present disclosure, an organic electroluminescent device having high efficiency and long lifespan is provided. In addition, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure, and is not meant in any way to restrict the scope of the present disclosure.
The organic electroluminescent device comprising the compound of formula 1 and the compound of formula 2 will be described in detail.
In formula 1, R1 to R8, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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, hydrogen, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted (10- to 30-membered)heteroaryl group, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C6-C12) aromatic ring; more preferably, hydrogen; a (C6-C15)aryl group unsubstituted or substituted with (C1-C6) alkyl group or tri(C6-C12)arylsilyl group; a (10- to 25-membered)heteroaryl group substituted with a substituted or unsubstituted (C6-C20)aryl group; or unsubstituted (20- to 30-membered)heteroaryl group; or may be linked to an adjacent substituent(s) to form an unsubstituted monocyclic (C6-C12) aromatic ring; and for example, hydrogen; phenyl unsubstituted or substituted with triphenylsilyl; fluorenyl substituted with methyl; carbazole unsubstituted or substituted with (C6-C20) aryl group which is unsubstituted or substituted with the substituent selected from the group consisting of cyano group, (C1-C6) alkyl group, (C6-C18) aryl group, and triphenylsilyl group; benzocarbazole substituted with phenyl; dibenzocarbazole substituted with phenyl; or nitrogen-containing (20-30 membered) heteroaryl group, or may be linked to an adjacent substituent(s) to form benzene.
R1 to R8 in formula 1, each independently, may be selected from the group consisting of:
Figure PCTKR2015012494-appb-I000003
Figure PCTKR2015012494-appb-I000004
Figure PCTKR2015012494-appb-I000005
Figure PCTKR2015012494-appb-I000006
Figure PCTKR2015012494-appb-I000007
wherein
L represents a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (5- to 20-membered)heteroarylene group; preferably, an unsubstituted (C6-C18)arylene group; more preferably, an unsubstituted (C6-C10)arylene group; and for example, phenylene;
n represents an integer of 0 to 2; and preferably, 0 or 1;
R21 to R25 and R31, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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, hydrogen, or a substituted or unsubstituted (C6-C20)aryl group; more preferably, hydrogen, or (C6-C20)aryl group which is unsubstituted or substituted with cyano group, (C1-C6) alkyl group, (C6-C18)aryl group or tri(C6-C12)arylsilyl group; and for example, hydrogen; phenyl unsubstituted or substituted with cyano group, naphthyl or triphenylsilyl; naphthyl unsubstituted or substituted with phenyl; biphenyl unsubstituted or substituted with naphthyl; terphenyl; phenanthrenyl; fluorenyl substituted with methyl or phenyl; fluoranthenyl; or perylenyl; and
the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P, and preferably, at least one hetero atom selected from N, O and S.
In formula 2, L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene group; more preferably, a single bond, or (C6-C12)arylene group which is unsubstituted or substituted with tri(C6-C10)arylsilyl group; and for example, a single bond, phenylene unsubstituted or substituted with triphenylsilyl, naphthylene, or biphenylene.
In formula 2, L1 may be represented by any one of the following formulae 7 to 19:
Figure PCTKR2015012494-appb-I000008
Figure PCTKR2015012494-appb-I000009
Figure PCTKR2015012494-appb-I000010
wherein
Xi to Xp, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be 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, hydrogen, a cyano group, a substituted or unsubstituted (C6-C15)aryl group, a substituted or unsubstituted (10- to 20-membered)heteroaryl group, or a substituted or unsubstituted tri(C6-C20)arylsilyl group; more preferably, hydrogen or an unsubstituted tri(C6-C10)arylsilyl group; and for example, hydrogen or unsubstituted triphenylsilyl.
In formula 2, Ar1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl group; preferably, a substituted or unsubstituted nitrogen-containing (5- to 11- membered)heteroayl group; more preferably, a nitrogen-containing (5- to 11- membered)heteroayl group unsubstituted or substituted with the substituent selected from the group consisting of (C6-C18) aryl group which is unsubstituted or substituted with a cyano group, (C1-C6) alkyl group, or tri(C6-C12)arylsilyl; and a (6- to 15- membered) heteroaryl group.
Also, Ar1 in formula 2 may be a monocyclic ring-type heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, or a fused ring-type heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl and phenanthridinyl; and preferably, triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, or quinoxalinyl.
In formula 2, R11 to R18 in formula 2, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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, hydrogen, a cyano group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted (10- to 20-membered)heteroaryl group, or a substituted or unsubstituted tri(C6-C12)arylsilyl group, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C6-C20) aromatic ring; more preferably, hydrogen; a cyano group; a (C6-C15)aryl group unsubstituted or substituted with a tri(C6-C10)arylsilyl; a (10- to 20-membered)heteroaryl group unsubstituted or substituted with a cyano group or a (C6-C12)aryl group; or an unsubstituted tri(C6-C10)arylsilyl group; or may be 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 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, preferably 5 to 7, ring backbone atoms, 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, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, 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 10 to 30 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, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc.; “nitrogen-containing (5- to 30-membered) heteroaryl(ene)” indicates an aryl group having 5 to 30 ring backbone atoms, preferably 10 to 30 ring backbone atoms, containing at least one, preferably 1 to 4, nitrogen as the hetero atom, may be 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 such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc. Furthermore, “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 alkoxy, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di- arylamino, the substituted mono- or di- alkylamino, or the substituted mono- or polycyclic, 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 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, at least one selected from the group consisting of a (C1-C6)alkyl; a (5- to 15-membered) heteroaryl; a (C6-C20)aryl unsubstituted or substituted with a cyano, (C6-C12)aryl or a tri(C6-C12)arylsilyl; a tri(C6-C12)arylsilyl; and a (C1-C6)alkyl(C6-C12)aryl.
The first host compound of formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
Figure PCTKR2015012494-appb-I000011
Figure PCTKR2015012494-appb-I000012
Figure PCTKR2015012494-appb-I000013
Figure PCTKR2015012494-appb-I000014
Figure PCTKR2015012494-appb-I000015
Figure PCTKR2015012494-appb-I000016
Figure PCTKR2015012494-appb-I000017
Figure PCTKR2015012494-appb-I000018
Figure PCTKR2015012494-appb-I000019
Figure PCTKR2015012494-appb-I000020
Figure PCTKR2015012494-appb-I000021
Figure PCTKR2015012494-appb-I000022
Figure PCTKR2015012494-appb-I000023
Figure PCTKR2015012494-appb-I000024
Figure PCTKR2015012494-appb-I000025
Figure PCTKR2015012494-appb-I000026
Figure PCTKR2015012494-appb-I000027
Figure PCTKR2015012494-appb-I000028
Figure PCTKR2015012494-appb-I000029
Figure PCTKR2015012494-appb-I000030
Figure PCTKR2015012494-appb-I000031
Figure PCTKR2015012494-appb-I000032
Figure PCTKR2015012494-appb-I000033
Figure PCTKR2015012494-appb-I000034
Figure PCTKR2015012494-appb-I000035
Figure PCTKR2015012494-appb-I000036
Figure PCTKR2015012494-appb-I000037
Figure PCTKR2015012494-appb-I000038
Figure PCTKR2015012494-appb-I000039
Figure PCTKR2015012494-appb-I000040
Figure PCTKR2015012494-appb-I000041
Figure PCTKR2015012494-appb-I000042
Figure PCTKR2015012494-appb-I000043
Figure PCTKR2015012494-appb-I000044
Figure PCTKR2015012494-appb-I000045
Figure PCTKR2015012494-appb-I000046
Figure PCTKR2015012494-appb-I000047
Figure PCTKR2015012494-appb-I000048
The second host compound of formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto:
Figure PCTKR2015012494-appb-I000049
Figure PCTKR2015012494-appb-I000050
Figure PCTKR2015012494-appb-I000051
Figure PCTKR2015012494-appb-I000052
Figure PCTKR2015012494-appb-I000053
Figure PCTKR2015012494-appb-I000054
Figure PCTKR2015012494-appb-I000055
Figure PCTKR2015012494-appb-I000056
Figure PCTKR2015012494-appb-I000057
Figure PCTKR2015012494-appb-I000058
Figure PCTKR2015012494-appb-I000060
Figure PCTKR2015012494-appb-I000061
Figure PCTKR2015012494-appb-I000062
Figure PCTKR2015012494-appb-I000063
Figure PCTKR2015012494-appb-I000064
Figure PCTKR2015012494-appb-I000065
Figure PCTKR2015012494-appb-I000066
Figure PCTKR2015012494-appb-I000067
Figure PCTKR2015012494-appb-I000068
Figure PCTKR2015012494-appb-I000069
Figure PCTKR2015012494-appb-I000070
Figure PCTKR2015012494-appb-I000071
Figure PCTKR2015012494-appb-I000072
Figure PCTKR2015012494-appb-I000073
Figure PCTKR2015012494-appb-I000074
Figure PCTKR2015012494-appb-I000075
Figure PCTKR2015012494-appb-I000076
Figure PCTKR2015012494-appb-I000077
Figure PCTKR2015012494-appb-I000078
Figure PCTKR2015012494-appb-I000079
Figure PCTKR2015012494-appb-I000080
Figure PCTKR2015012494-appb-I000081
Figure PCTKR2015012494-appb-I000082
Figure PCTKR2015012494-appb-I000083
Figure PCTKR2015012494-appb-I000084
Figure PCTKR2015012494-appb-I000085
Figure PCTKR2015012494-appb-I000086
Figure PCTKR2015012494-appb-I000087
Figure PCTKR2015012494-appb-I000088
Figure PCTKR2015012494-appb-I000089
Figure PCTKR2015012494-appb-I000090
Figure PCTKR2015012494-appb-I000091
Figure PCTKR2015012494-appb-I000092
Figure PCTKR2015012494-appb-I000093
Figure PCTKR2015012494-appb-I000094
Figure PCTKR2015012494-appb-I000095
Figure PCTKR2015012494-appb-I000096
Figure PCTKR2015012494-appb-I000097
Figure PCTKR2015012494-appb-I000098
Figure PCTKR2015012494-appb-I000099
Figure PCTKR2015012494-appb-I000100
Figure PCTKR2015012494-appb-I000101
Figure PCTKR2015012494-appb-I000102
Figure PCTKR2015012494-appb-I000103
Figure PCTKR2015012494-appb-I000104
Figure PCTKR2015012494-appb-I000105
Figure PCTKR2015012494-appb-I000106
Figure PCTKR2015012494-appb-I000107
Figure PCTKR2015012494-appb-I000108
Figure PCTKR2015012494-appb-I000109
Figure PCTKR2015012494-appb-I000110
The organic electroluminescent device of the present disclosure comprises an anode; a cathode; and at least one organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; the light-emitting layer comprises a host and a phosphorescent dopant; the host comprises a plurality of host compounds; and at least a first host compound of a plurality of host compounds is represented by formula 1, and a second host compound is represented by formula 2.
The light-emitting layer indicates a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
In the organic electroluminescent device of the present disclosure, the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
The dopant to be comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant. The phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
Preferably, the phosphorescent dopant may be selected from the group consisting of compounds represented by the following formulae 101 to 103.
Figure PCTKR2015012494-appb-I000111
wherein La is selected from the following structures:
Figure PCTKR2015012494-appb-I000112
R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
R101 to R109 and R111 to R123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; R106 to R109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl group; R120 to R123 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a quinoline unsubstituted or substituted with an alkyl or aryl;
R124 to R127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R124 to R127 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R208 to R211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
r and s each independently represent an integer of 1 to 3; when 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 material includes the following:
Figure PCTKR2015012494-appb-I000113
Figure PCTKR2015012494-appb-I000114
Figure PCTKR2015012494-appb-I000115
Figure PCTKR2015012494-appb-I000116
Figure PCTKR2015012494-appb-I000117
Figure PCTKR2015012494-appb-I000118
Figure PCTKR2015012494-appb-I000119
Figure PCTKR2015012494-appb-I000120
Figure PCTKR2015012494-appb-I000121
Figure PCTKR2015012494-appb-I000122
Figure PCTKR2015012494-appb-I000123
Figure PCTKR2015012494-appb-I000124
Figure PCTKR2015012494-appb-I000125
Figure PCTKR2015012494-appb-I000126
Figure PCTKR2015012494-appb-I000127
Figure PCTKR2015012494-appb-I000128
Figure PCTKR2015012494-appb-I000129
Figure PCTKR2015012494-appb-I000130
Figure PCTKR2015012494-appb-I000131
Figure PCTKR2015012494-appb-I000132
Figure PCTKR2015012494-appb-I000133
Figure PCTKR2015012494-appb-I000134
Figure PCTKR2015012494-appb-I000135
Figure PCTKR2015012494-appb-I000136
Figure PCTKR2015012494-appb-I000137
Figure PCTKR2015012494-appb-I000138
Figure PCTKR2015012494-appb-I000139
The organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds at the organic layer.
Also, in the organic electroluminescent device of the present disclosure, 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
Preferably, in the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "a surface layer”) may be 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 (includes 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, the chalcogenide includes SiOX (1≤X≤2), AlOX (1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer. The hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds. The hole transport layer or electron blocking layer may be composed of two or more layers.
An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode. The electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
In the organic electroluminescent device of the present disclosure, 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 may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, 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 light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used.
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.
In the organic electroluminescent device of the present disclosure, the first host compound and the second host compound may be film-formed by co-evaporaton or mixture-evaporaton.
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 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 electric current to the cell for the mixture to be evaporated.
Also, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
Hereinafter, the luminescent properties of the device comprising the host compound of the present disclosure will be explained in detail with reference to the following examples.
[Device Example 1-1] Production of an OLED device by a co-evaporation
of a first host compound and a second host compound of the present disclosure
An OLED device was produced using the light-emitting material of the present disclosure as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then 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 the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-1, 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 then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying 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 introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying 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)-(4-(9-dibenzo[b,d]furan-4-yl)-9H-fluorene-9-yl)phenyl)-[1,1’-biphenyl]-4-amine (compound HT-2) was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. As a host material, compound K-1 and compound H2-125 were introduced into two cells of the vacuum vapor depositing apparatus, respectively. A compound D-1 was introduced into another cell as a dopant. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 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. Next, 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (compound ET-1) and lithium quinolate (compound EI-1) were evaporated at the rate of 4:6 on another two cells of the vacuum vapor depositing apparatus to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing lithium quinolate (compound EI-1) having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced.
Figure PCTKR2015012494-appb-I000140
[Comparative Example 1-1] Production of an OLED device comprising a
first host compound as a sole host
An OLED device was produced in the same manner as in Device Example 1-1, except that only a first host compound of K-1 was used as a host for a light-emitting layer.
[Comparative Example 1-2] Production of an OLED device comprising a
second host compound as a sole host
An OLED device was produced in the same manner as in Device Example 1-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
The driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 90% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 1-1, and Comparative Examples 1-1 and 1-2 are shown in Table 1 below.
Figure PCTKR2015012494-appb-I000141
[Device Example 2-1] Production of OLED by a co-evaporation of a first
host compound and a second host compound of the present disclosure
An OLED device was produced in the same manner as in Device Example 1-1, except that compound D-25 was used as a dopant.
[Comparative Example 2-1] Production of an OLED device comprising a
second host compound as a sole host
An OLED device was produced in the same manner as in Device Example 2-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
The driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 97% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 2-1 and Comparative Example 2-1 are shown in Table 2 below.
Figure PCTKR2015012494-appb-I000142
[Device Example 3-1] Production of OLED by a co-evaporation of a first
host compound and a second host compound of the present disclosure
An OLED device was produced in the same manner as in Device Example 1-1, except that compound D-136 was used as a dopant.
[Comparative Example 3-1] Production of an OLED device comprising a
second host compound as a sole host
An OLED device was produced in the same manner as in Device Example 3-1, except that only a second host compound of H2-125 was used as a host for a light-emitting layer.
The driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 95% based on a luminance of 15,000 nits of the organic electroluminescent devices produced in Device Example 3-1 and Comparative Example 3-1 are shown in Table 3 below.
Figure PCTKR2015012494-appb-I000143
[Device Examples 4-1 to 4-4] Production of an OLED device by a
co-evaporation of a first host compound and a second host compound of the present disclosure
An OLED device was produced using the light-emitting material of the present disclosure as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. Compound HI-2 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-2, thereby forming a hole injection layer having a thickness of 5 nm on the ITO substrate. Compound NPB was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 95 nm on the hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 20 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, a light-emitting layer was then deposited as follows. As a host material, a first host compound and a second host compound of Device Examples 4-1 to 4-4 shown in Table 4 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively. Compound D-125 was introduced into another cell as a dopant. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 12 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Next, compound ET-2 was deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced.
Figure PCTKR2015012494-appb-I000144
[Comparative Examples 4-1 and 4-2] Production of an OLED device
comprising a second host compound as a sole host
An OLED device was produced in the same manner as in Device Examples 4-1 to 4-4, except that only a host compound of Comparative Examples 4-1 and 4-2 shown in Table 4 was used as a sole host for a light-emitting layer.
The driving voltage, a luminous efficiency and a CIE color coordinate based on 10 mA/cm2 of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 97% based on a luminance of 10,000 nits of the organic electroluminescent devices produced in Device Examples 4-1 to 4-4 and Comparative Examples 4-1 and 4-2 are shown in Table 4 below.
Figure PCTKR2015012494-appb-I000145
[Device Examples 5-1 and 5-2] Production of OLED by a co-evaporation of
a first host compound and a second host compound of the present disclosure
An OLED device was produced in the same manner as in Device Example 1-1, except that the second hole injection layer was deposited as a thickness of 5 nm, compound HT-3 was deposited as the second hole transport layer having a thickness of 60 nm, a first host compound and a second host compound of Device Examples 5-1 and 5-2 shown in Table 5 were used, compound D-96 was deposited in a doping amount of 3 wt% as a dopant, and the electron transport layer was deposited as a thickness of 30 nm at the rate of 1:1.
Figure PCTKR2015012494-appb-I000146
[Comparative Example 5-1] Production of an OLED device comprising a
second host compound as a sole host
An OLED device was produced in the same manner as in Device Example 5-1, except that only a second host compound of H2-41 was used as a host for a light-emitting layer.
The driving voltage, a luminous efficiency and a CIE color coordinate based on a luminance of 1,000 nits of the organic electroluminescent devices, and the minimum time taken for luminance to be reduced from 100% to 98% based on a luminance of 5,000 nits of the organic electroluminescent devices produced in Device Examples 5-1 and 5-2, and Comparative Example 5-1 are shown in Table 5 below.
Figure PCTKR2015012494-appb-I000147
The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By using a plurality of host materials of the present disclosure, it is possible to produce an organic electroluminescent device having excellent current efficiency and power efficiency and improved driving lifespan compared to conventional devices using only a sole host.

Claims (7)

  1. An organic electroluminescent device comprising at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host comprises a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
    Figure PCTKR2015012494-appb-I000148
    and
    a second host compound is represented by the following formula 2:
    Figure PCTKR2015012494-appb-I000149
    wherein
    Ar1 represents a substituted or unsubstituted (3- to 30-membered)heteroaryl group;
    provided that Ar1 is not the structure of
    Figure PCTKR2015012494-appb-I000150
    or a carbazole;
    L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
    R1 to R8 and R11 to R18, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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 group 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 R1 to R8 in formula 1, each independently, are selected from the group consisting of:
    Figure PCTKR2015012494-appb-I000151
    Figure PCTKR2015012494-appb-I000152
    Figure PCTKR2015012494-appb-I000153
    Figure PCTKR2015012494-appb-I000154
    Figure PCTKR2015012494-appb-I000155
    wherein
    L represents a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (5- to 20-membered)heteroarylene group;
    n represents an integer of 0 to 2;
    R21 to R25 and R31, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be 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 group contains at least one hetero atom selected from B, N, O, S, Si, and P.
  3. The organic electroluminescent device according to claim 1, wherein L1 in formula 2 is represented by any one of the following formulae 7 to 19:
    Figure PCTKR2015012494-appb-I000156
    Figure PCTKR2015012494-appb-I000157
    Figure PCTKR2015012494-appb-I000158
    wherein
    Xi to Xp, each independently, represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be 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 Ar1 in formula 2 may be a monocyclic ring-type heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, or a fused ring-type heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl and phenanthridinyl.
  5. The organic electroluminescent device according to claim 1, wherein R11 to R18 in formula 2, each independently, represent hydrogen, a cyano group, a (C6-C15)aryl group unsubstituted or substituted with a tri(C6-C10)arylsilyl, a (10- to 20-membered)heteroaryl group unsubstituted or substituted with a cyano or a (C6-C12)aryl, or an unsubstituted tri(C6-C10)arylsilyl group; or may be 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.
  6. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2015012494-appb-I000159
    Figure PCTKR2015012494-appb-I000160
    Figure PCTKR2015012494-appb-I000161
    Figure PCTKR2015012494-appb-I000162
    Figure PCTKR2015012494-appb-I000163
    Figure PCTKR2015012494-appb-I000164
    Figure PCTKR2015012494-appb-I000165
    Figure PCTKR2015012494-appb-I000166
    Figure PCTKR2015012494-appb-I000167
    Figure PCTKR2015012494-appb-I000168
    Figure PCTKR2015012494-appb-I000169
    Figure PCTKR2015012494-appb-I000170
    Figure PCTKR2015012494-appb-I000171
    Figure PCTKR2015012494-appb-I000172
    Figure PCTKR2015012494-appb-I000173
    Figure PCTKR2015012494-appb-I000174
    Figure PCTKR2015012494-appb-I000175
    Figure PCTKR2015012494-appb-I000176
    Figure PCTKR2015012494-appb-I000177
    Figure PCTKR2015012494-appb-I000178
    Figure PCTKR2015012494-appb-I000179
    Figure PCTKR2015012494-appb-I000180
    Figure PCTKR2015012494-appb-I000181
    Figure PCTKR2015012494-appb-I000182
    Figure PCTKR2015012494-appb-I000183
    Figure PCTKR2015012494-appb-I000184
    Figure PCTKR2015012494-appb-I000185
    Figure PCTKR2015012494-appb-I000186
    Figure PCTKR2015012494-appb-I000187
    Figure PCTKR2015012494-appb-I000188
    Figure PCTKR2015012494-appb-I000189
    Figure PCTKR2015012494-appb-I000190
    Figure PCTKR2015012494-appb-I000191
    Figure PCTKR2015012494-appb-I000192
    Figure PCTKR2015012494-appb-I000193
    Figure PCTKR2015012494-appb-I000194
    Figure PCTKR2015012494-appb-I000195
    Figure PCTKR2015012494-appb-I000196
  7. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
    Figure PCTKR2015012494-appb-I000197
    Figure PCTKR2015012494-appb-I000198
    Figure PCTKR2015012494-appb-I000199
    Figure PCTKR2015012494-appb-I000200
    Figure PCTKR2015012494-appb-I000201
    Figure PCTKR2015012494-appb-I000202
    Figure PCTKR2015012494-appb-I000203
    Figure PCTKR2015012494-appb-I000204
    Figure PCTKR2015012494-appb-I000205
    Figure PCTKR2015012494-appb-I000206
    Figure PCTKR2015012494-appb-I000207
    Figure PCTKR2015012494-appb-I000208
    Figure PCTKR2015012494-appb-I000209
    Figure PCTKR2015012494-appb-I000210
    Figure PCTKR2015012494-appb-I000211
    Figure PCTKR2015012494-appb-I000212
    Figure PCTKR2015012494-appb-I000213
    Figure PCTKR2015012494-appb-I000214
    Figure PCTKR2015012494-appb-I000215
    Figure PCTKR2015012494-appb-I000216
    Figure PCTKR2015012494-appb-I000217
    Figure PCTKR2015012494-appb-I000218
    Figure PCTKR2015012494-appb-I000219
    Figure PCTKR2015012494-appb-I000220
    Figure PCTKR2015012494-appb-I000221
    Figure PCTKR2015012494-appb-I000222
    Figure PCTKR2015012494-appb-I000223
    Figure PCTKR2015012494-appb-I000224
    Figure PCTKR2015012494-appb-I000225
    Figure PCTKR2015012494-appb-I000226
    Figure PCTKR2015012494-appb-I000227
    Figure PCTKR2015012494-appb-I000228
    Figure PCTKR2015012494-appb-I000229
    Figure PCTKR2015012494-appb-I000230
    Figure PCTKR2015012494-appb-I000231
    Figure PCTKR2015012494-appb-I000232
    Figure PCTKR2015012494-appb-I000233
    Figure PCTKR2015012494-appb-I000234
    Figure PCTKR2015012494-appb-I000235
    Figure PCTKR2015012494-appb-I000236
    Figure PCTKR2015012494-appb-I000237
    Figure PCTKR2015012494-appb-I000238
    Figure PCTKR2015012494-appb-I000239
    Figure PCTKR2015012494-appb-I000240
    Figure PCTKR2015012494-appb-I000241
    Figure PCTKR2015012494-appb-I000242
    Figure PCTKR2015012494-appb-I000243
    Figure PCTKR2015012494-appb-I000244
    Figure PCTKR2015012494-appb-I000245
    Figure PCTKR2015012494-appb-I000246
    Figure PCTKR2015012494-appb-I000247
    Figure PCTKR2015012494-appb-I000248
    Figure PCTKR2015012494-appb-I000249
    Figure PCTKR2015012494-appb-I000250
    Figure PCTKR2015012494-appb-I000251
    Figure PCTKR2015012494-appb-I000252
    Figure PCTKR2015012494-appb-I000253
    Figure PCTKR2015012494-appb-I000254
    Figure PCTKR2015012494-appb-I000255
    Figure PCTKR2015012494-appb-I000256
    Figure PCTKR2015012494-appb-I000257
    Figure PCTKR2015012494-appb-I000258
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