WO2015046916A1 - A combination of a host compound and a dopant compound - Google Patents

A combination of a host compound and a dopant compound Download PDF

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Publication number
WO2015046916A1
WO2015046916A1 PCT/KR2014/008963 KR2014008963W WO2015046916A1 WO 2015046916 A1 WO2015046916 A1 WO 2015046916A1 KR 2014008963 W KR2014008963 W KR 2014008963W WO 2015046916 A1 WO2015046916 A1 WO 2015046916A1
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substituted
unsubstituted
compound
group
mmol
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Inventor
Kyung-Joo Lee
Seok-Keun Yoon
Chi-Sik Kim
Hyun Kim
Seon-Woo Lee
So-Young Jung
Su-Hyun Lee
Jeong-Eun YANG
Young-Kwang Kim
Young-Jun Cho
Kyoung-Jin Park
Sung-Woo Jang
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Publication of WO2015046916A1 publication Critical patent/WO2015046916A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a combination of specific dopant and host compounds.
  • An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].
  • the organic EL device changes electric energy into light by the injection of a charge into an organic light-emitting material and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing host and dopant materials), an electron transport layer (ETL), a hole blocking layer (HBL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron transport material, a hole blocking material, an electron injection material, etc., depending on functions.
  • the organic EL device In the organic EL device, holes from an anode and electrons from a cathode are injected to a light-emitting layer by the injection of a charge, and an exciton having high energy is produced by the recombination of holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light which is changed from energy when the organic light-emitting compound returns to the ground state from the excited state.
  • the light-emitting material is required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, formability of a uniformlayer, and stability.
  • the light-emitting material is classified into blue light-emitting materials, green light-emitting materials according to the light-emitting color, and red light-emitting materials, and further includes yellow light-emitting materials or orange light-emitting materials.
  • the light-emitting material is classified into a host material and a dopant material in the functional aspect.
  • the light-emitting layer wherein a dopant is doped onto a host
  • a host material should have high purity and suitable molecular weight in order to be deposited under vacuum.
  • a host material is required to have high glass transition temperature and pyrolysis temperature to guarantee thermal stability, high electrochemical stability to provide long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
  • the light-emitting materials are classified into fluorescent materials (singlet excited state) and phosphorescent materials (triplet excited state) according to the excited state.
  • the fluorescent materials were initially used in an organic EL device.
  • phosphorescent materials have efficiency for changing electricity into light (luminous efficiency) by four (4) times over fluorescent materials, reduce consumption power, and improve lifespan. Thus, development of phosphorescent materials are widely being conducted.
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium (Firpic) as red, green and blue materials, respectively.
  • a mixed system of a dopant/host material can be used as a light-emitting material to improve color purity, luminous efficiency, and stability.
  • the device having excellent EL properties comprises the light-emitting layer, wherein a dopant is doped onto a host. If the dopant/host material system is used, the selection of the host material is important since the host material greatly influences the efficiency and performance of a light-emitting device.
  • 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known as a phosphorescent host material.
  • the organic EL device comprising light-emitting materials containing conventional dopant and host compounds does not have good power efficiency, satisfactory operating lifespan and high luminous efficiency.
  • Korean Patent Application Laid-open Nos. 2013-0054205 and 2011-0130475, and US 2013/0026452 A1 disclose heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands as dopant compounds included in light-emitting materials of an organic EL device, but do not mention a combination with specific host compounds suitable for the dopant compounds.
  • the present inventors have found that the light-emitting materials containing a specific combination of dopant compounds and host compounds are more effective in improving power efficiency and luminous efficiency of the organic EL device over conventional light-emitting materials.
  • the object of the present invention is to provide a specific combination of dopant compounds and host compounds which can improve the power efficiency of an organic EL device by reducing the driving voltage of the organic EL device.
  • L 1 to L 3 are each independently selected from the following structures, with the proviso that at least one of L 1 to L 3 represents A-1, A-2 or A-3:
  • X represents O or S
  • R 1 to R 11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; and
  • a to h each independently represent an integer of 0 to 4; where a to h is an integer of 2 or more, each of R 1 to each of R 8 is the same or different.
  • Y 1 represents O, S, NR 31 or CR 32 R 33 ;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
  • R 21 to R 23 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 5- to 30-membered heteroaryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amino group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group containing a nitrogen atom;
  • R 31 to R 33 each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • n and o each independently represent an integer of 0 to 4; where m or o is an integer of 2 or more, each of R 21 or each of R 23 is the same or different;
  • n represents an integer of 0 to 2; where n is 2, each of R 22 is the same or different; and
  • the organic EL device comprising a combination of the dopant and host compounds according to the present invention has excellent light-emitting property and improves the power efficiency of an organic EL device by reducing the driving voltage of the organic EL device.
  • the present invention relates to a combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
  • R 1 to R 11 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C3-C10)cycloalkyl group, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group.
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group
  • R 21 to R 23 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted silyl group
  • Ar 1 represents a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group containing a nitrogen atom.
  • the dopant compound of formula 1 is represented by the following formula 3, 4, or 5:
  • R 1 to R 6 , a to f, X, L 2 and L 3 are as defined in formula 1.
  • the compound of formula 3 can be specifically exemplified as the following compounds:
  • the compound of formula 4 can be specifically exemplified as the following compounds:
  • the compound of formula 5 can be specifically exemplified as the following compounds:
  • the host compound of formula 2 is represented by one of the following formulae 6 to 11:
  • R 21 to R 23 , Y 1 , L 4 , Ar 1 , m, n and o are as defined in formula 2.
  • the compounds of formulae 6 to 11 can be specifically exemplified as the following compounds:
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • 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.
  • Substituents of the substituted (C1-C30)alkyl group, the substituted (C3-C30)cycloalkyl group, the substituted (C6-C30)aryl group, and the substituted 5- to 30-membered heteroaryl group in the formulae of the present invention each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group which is unsubstituted or substituted with halogen(s); a (C2-C30)alkenyl group; (C2-C30)alkynyl group; a (C1-C30)alkoxy
  • the organic electroluminescent device comprising a combination of the dopant and host compounds according to the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises a light-emitting layer which contains at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
  • the light-emitting layer emitting light may be a single layer or a multiple layer having two or more layers.
  • the doping concentration of dopant compounds to host compounds in the light-emitting layer is preferably less than 20 wt%.
  • the present invention provides a host/dopant combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2. Furthermore, the present invention provides an organic electroluminescent device comprising the host/dopant combination.
  • the present invention provides the organic layer containing at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
  • the organic layer comprises multiple layers, and the dopant and host compounds may be included in one layer or separate layers.
  • the present invention provides an organic electroluminescent device comprising the organic layer.
  • the organic electroluminescent device of the present invention may further include 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 the metal.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • the surface layer provides operating 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 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 a light-emitting 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 a light-emitting 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
  • a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
  • 2-Bromo-9,9-dimethyl-9H-fluorene (80.0 g, 291.0 mmol), 2-chlorobenzenamine (45.0 mL, 437.0 mmol), palladium(II) acetate [Pd(OAc) 2 ] (2.6 g, 12.0 mmol), tri-tert-butylphosphine [P(t-Bu) 3 ] (12.0 mL, 24.0 mmol), sodium tert-butoxide (NaOt-Bu) (70.0 g, 728.0 mmol), and toluene (800.0 mL) were mixed in a flask, heated to 120°C and stirred for 9 hrs.
  • An organic light-emitting diode (OLED) device comprising the light-emitting material of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • ITO indium tin oxide
  • N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalene-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) 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 the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • Compound H-60 was introduced as a host into one cell of the vacuum vapor depositing apparatus, and compound D-3 as a dopant was introduced into another cell.
  • the two materials were evaporated at different rates and the dopant was deposited in a doping amount of 15 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidiazole was introduced into one cell, and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rates and were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
  • the produced OLED device showed green emission having power efficiency of 44.01 m/W and a luminance of 1620 cd/m 2 at 3.6 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-135 was used as a host and compound D-3 was used as a dopant in a light-emitting material.
  • the produced OLED device showed green emission having power efficiency of 56.61 m/W and a luminance of 2190 cd/m 2 at 2.6 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-176 was used as a host and compound D-3 was used as a dopant in a light-emitting material.
  • the produced OLED device showed green emission having power efficiency of 51.91 m/W and a luminance of 2510 cd/m 2 at 2.6 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-135 was used as a host and compound D-96 was used as a dopant in a light-emitting material.
  • the produced OLED device showed green emission having power efficiency of 47.71 m/W and a luminance of 3140 cd/m 2 at 2.6 V.
  • Comparative Example 1 Production of an OLED device by using
  • An OLED device was produced in the same manner as in Device Example 1, except that comparative compound 1 was used as a hostand compound D-2 was used as a dopant in a light-emitting material; a light-emitting layer having a thickness of 30 nm is formed on the hole transport layer; and 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene having a thickness of 10 nm as a hole blocking layer is formed.
  • the produced OLED device showed green emission having power efficiency of 16.81 m/W and a luminance of 3000 cd/m 2 at 6.9 V.
  • the organic electroluminescent compound of the present invention provides higher luminance efficiency and power efficiency at lower driving voltage than the device comprising conventional light-emitting materials by comprising a combination of specific dopant and host compounds in a light-emitting layer, and thus improves consumption power.

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Abstract

The present invention relates to a specific combination of dopant compounds and host compounds. By using a combination of the dopant and host compounds according to the present invention, an organic electroluminescent device has improved current efficiency compared with conventional light-emitting material, and thus has improved power efficiency at a low driving voltage.

Description

A COMBINATION OF A HOST COMPOUND AND A DOPANT COMPOUND
The present invention relates to a combination of specific dopant and host compounds.
An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].
The organic EL device changes electric energy into light by the injection of a charge into an organic light-emitting material and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing host and dopant materials), an electron transport layer (ETL), a hole blocking layer (HBL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron transport material, a hole blocking material, an electron injection material, etc., depending on functions. In the organic EL device, holes from an anode and electrons from a cathode are injected to a light-emitting layer by the injection of a charge, and an exciton having high energy is produced by the recombination of holes and electrons. The organic light-emitting compound moves into an excited state by the energy and emits light which is changed from energy when the organic light-emitting compound returns to the ground state from the excited state.
The most important factor determining properties, such as luminous efficiency, etc., in an organic EL device is the light-emitting material. The light-emitting material is required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, formability of a uniformlayer, and stability. The light-emitting material is classified into blue light-emitting materials, green light-emitting materials according to the light-emitting color, and red light-emitting materials, and further includes yellow light-emitting materials or orange light-emitting materials. Furthermore, the light-emitting material is classified into a host material and a dopant material in the functional aspect. Generally, as a structure of the device having the most excellent EL properties, the light-emitting layer, wherein a dopant is doped onto a host, was known. Recently, an urgent task is the development of an organic EL device having high efficacy and a long operating lifespan. In particular, the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels. For this, preferably, as a solvent in a solid state and energy transmitter, a host material should have high purity and suitable molecular weight in order to be deposited under vacuum. Furthermore, a host material is required to have high glass transition temperature and pyrolysis temperature to guarantee thermal stability, high electrochemical stability to provide long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
The light-emitting materials are classified into fluorescent materials (singlet excited state) and phosphorescent materials (triplet excited state) according to the excited state. The fluorescent materials were initially used in an organic EL device. However, phosphorescent materials have efficiency for changing electricity into light (luminous efficiency) by four (4) times over fluorescent materials, reduce consumption power, and improve lifespan. Thus, development of phosphorescent materials are widely being conducted.
Until now, Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium (Firpic) as red, green and blue materials, respectively.
A mixed system of a dopant/host material can be used as a light-emitting material to improve color purity, luminous efficiency, and stability. Generally, the device having excellent EL properties comprises the light-emitting layer, wherein a dopant is doped onto a host. If the dopant/host material system is used, the selection of the host material is important since the host material greatly influences the efficiency and performance of a light-emitting device. In conventional technique, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known as a phosphorescent host material. Pioneer (Japan) et al., currently developed a high performance organic EL device by employing bathocuproine (BCP), aluminum(III) bis(2-methyl-8-quinolinato)(4-phenylphenolate) (BAlq), etc., which were used in a hole blocking layer, as host materials.
Although these phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperatures and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of an organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to voltage. An organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) and has a higher driving voltage than one comprising fluorescent host materials. Thus, the organic EL device using conventional phosphorescent materials has no advantage in terms of power efficiency (lm/W). (3) Furthermore, the operating lifespan, and luminous efficiency of the organic EL device are not satisfactory.
Thus, the organic EL device comprising light-emitting materials containing conventional dopant and host compounds does not have good power efficiency, satisfactory operating lifespan and high luminous efficiency.
Korean Patent Application Laid-open Nos. 2013-0054205 and 2011-0130475, and US 2013/0026452 A1 disclose heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands as dopant compounds included in light-emitting materials of an organic EL device, but do not mention a combination with specific host compounds suitable for the dopant compounds.
The present inventors have found that the light-emitting materials containing a specific combination of dopant compounds and host compounds are more effective in improving power efficiency and luminous efficiency of the organic EL device over conventional light-emitting materials.
The object of the present invention is to provide a specific combination of dopant compounds and host compounds which can improve the power efficiency of an organic EL device by reducing the driving voltage of the organic EL device.
The above objective can be achieved by a combination of at least one dopant compound represented by the following formula 1 and at least one host compound represented by the following formula 2:
Figure PCTKR2014008963-appb-I000001
wherein
L1 to L3 are each independently selected from the following structures, with the proviso that at least one of L1 to L3 represents A-1, A-2 or A-3:
Figure PCTKR2014008963-appb-I000002
X represents O or S;
R1 to R11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; and
a to h each independently represent an integer of 0 to 4; where a to h is an integer of 2 or more, each of R1 to each of R8 is the same or different.
Figure PCTKR2014008963-appb-I000003
wherein
Y1 represents O, S, NR31 or CR32R33;
L4 represents a single bond, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
R21 to R23 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 5- to 30-membered heteroaryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amino group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group containing a nitrogen atom;
R31 to R33 each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
m and o each independently represent an integer of 0 to 4; where m or o is an integer of 2 or more, each of R21 or each of R23 is the same or different;
n represents an integer of 0 to 2; where n is 2, each of R22 is the same or different; and
the heteroaryl group contains at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
The organic EL device comprising a combination of the dopant and host compounds according to the present invention has excellent light-emitting property and improves the power efficiency of an organic EL device by reducing the driving voltage of the organic EL device.
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 present invention relates to a combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
In the compound of formula 1, preferably, R1 to R11 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C3-C10)cycloalkyl group, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group. In the compound of formula 2, preferably, L4 represents a single bond, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group, R21 to R23 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted silyl group, and Ar1 represents a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group containing a nitrogen atom.
The dopant compound of formula 1 is represented by the following formula 3, 4, or 5:
Figure PCTKR2014008963-appb-I000004
Figure PCTKR2014008963-appb-I000005
Figure PCTKR2014008963-appb-I000006
wherein
R1 to R6, a to f, X, L2 and L3 are as defined in formula 1.
The compound of formula 3 can be specifically exemplified as the following compounds:
Figure PCTKR2014008963-appb-I000007
Figure PCTKR2014008963-appb-I000008
Figure PCTKR2014008963-appb-I000009
Figure PCTKR2014008963-appb-I000010
Figure PCTKR2014008963-appb-I000011
Figure PCTKR2014008963-appb-I000012
Figure PCTKR2014008963-appb-I000013
Figure PCTKR2014008963-appb-I000014
Figure PCTKR2014008963-appb-I000015
Figure PCTKR2014008963-appb-I000016
Figure PCTKR2014008963-appb-I000017
Figure PCTKR2014008963-appb-I000018
Figure PCTKR2014008963-appb-I000019
Figure PCTKR2014008963-appb-I000020
Figure PCTKR2014008963-appb-I000021
Figure PCTKR2014008963-appb-I000022
Figure PCTKR2014008963-appb-I000023
Figure PCTKR2014008963-appb-I000024
Figure PCTKR2014008963-appb-I000025
Figure PCTKR2014008963-appb-I000026
The compound of formula 4 can be specifically exemplified as the following compounds:
Figure PCTKR2014008963-appb-I000027
Figure PCTKR2014008963-appb-I000028
Figure PCTKR2014008963-appb-I000029
Figure PCTKR2014008963-appb-I000030
Figure PCTKR2014008963-appb-I000031
Figure PCTKR2014008963-appb-I000032
Figure PCTKR2014008963-appb-I000033
Figure PCTKR2014008963-appb-I000034
The compound of formula 5 can be specifically exemplified as the following compounds:
Figure PCTKR2014008963-appb-I000035
Figure PCTKR2014008963-appb-I000036
Figure PCTKR2014008963-appb-I000037
Figure PCTKR2014008963-appb-I000038
Figure PCTKR2014008963-appb-I000039
Figure PCTKR2014008963-appb-I000040
The host compound of formula 2 is represented by one of the following formulae 6 to 11:
Figure PCTKR2014008963-appb-I000041
Figure PCTKR2014008963-appb-I000042
Figure PCTKR2014008963-appb-I000043
Figure PCTKR2014008963-appb-I000044
Figure PCTKR2014008963-appb-I000045
Figure PCTKR2014008963-appb-I000046
wherein
R21 to R23, Y1, L4, Ar1, m, n and o are as defined in formula 2.
The compounds of formulae 6 to 11 can be specifically exemplified as the following compounds:
Figure PCTKR2014008963-appb-I000047
Figure PCTKR2014008963-appb-I000048
Figure PCTKR2014008963-appb-I000049
Figure PCTKR2014008963-appb-I000050
Figure PCTKR2014008963-appb-I000051
Figure PCTKR2014008963-appb-I000052
Figure PCTKR2014008963-appb-I000053
Figure PCTKR2014008963-appb-I000054
Figure PCTKR2014008963-appb-I000055
Figure PCTKR2014008963-appb-I000056
Figure PCTKR2014008963-appb-I000057
Figure PCTKR2014008963-appb-I000058
Figure PCTKR2014008963-appb-I000059
Figure PCTKR2014008963-appb-I000060
Figure PCTKR2014008963-appb-I000061
Figure PCTKR2014008963-appb-I000062
Figure PCTKR2014008963-appb-I000063
Figure PCTKR2014008963-appb-I000064
Figure PCTKR2014008963-appb-I000065
Figure PCTKR2014008963-appb-I000066
Figure PCTKR2014008963-appb-I000067
Figure PCTKR2014008963-appb-I000068
Figure PCTKR2014008963-appb-I000069
Herein, “(C1-C30)alkyl(ene)” is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C2-C30)alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; has preferably 3 to 20, more preferably 3 to 15 ring backbone atoms; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “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. Substituents of the substituted (C1-C30)alkyl group, the substituted (C3-C30)cycloalkyl group, the substituted (C6-C30)aryl group, and the substituted 5- to 30-membered heteroaryl group in the formulae of the present invention each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group which is unsubstituted or substituted with halogen(s); a (C2-C30)alkenyl group; (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 3- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a (C6-C30)aryl group which is unsubstituted or substituted with a 3- to 30-membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di(C1-C30)alkylamino group; a mono- or di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group.
The organic electroluminescent device comprising a combination of the dopant and host compounds according to the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises a light-emitting layer which contains at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2.
The light-emitting layer emitting light may be a single layer or a multiple layer having two or more layers. The doping concentration of dopant compounds to host compounds in the light-emitting layer is preferably less than 20 wt%.
According to another embodiment, the present invention provides a host/dopant combination of at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2. Furthermore, the present invention provides an organic electroluminescent device comprising the host/dopant combination.
According to another embodiment, the present invention provides the organic layer containing at least one dopant compound represented by formula 1 and at least one host compound represented by formula 2. The organic layer comprises multiple layers, and the dopant and host compounds may be included in one layer or separate layers. Furthermore, the present invention provides an organic electroluminescent device comprising the organic layer.
The organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In the organic electroluminescent device of 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 the metal.
Preferably, in the organic electroluminescent device of the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. The surface layer provides operating 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.
Preferably, in the organic electroluminescent device of the present invention, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant 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 a light-emitting 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 a light-emitting medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device of the present invention, dry film-forming methods, such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
Hereinafter, the representative dopant and host compounds of the present invention, the preparation methods of the compounds, and the properties of the light-emitting device comprising their combinations will be explained in detail with reference to the following examples:
Example 1: Preparation of compound D-2
Figure PCTKR2014008963-appb-I000070
Figure PCTKR2014008963-appb-I000071
Preparation of compound 1-1
2-Phenylpyridine (10.0 g, 32.0 mmol), iridium(III) chloride hydrate (IrCl3·xH2O) (8.1 g, 29.0 mmol), 2-ethoxyethanol (220.0 mL), and H2O (74.0 mL) in a flask were stirred at 140°C for 24 hrs. After completing the reaction, the mixture was cooled to room temperature, washed with H2O and methanol (MeOH), and then dried to obtain compound 1-1 (11.0 g, 71 %).
Preparation of compound 1-2
Compound 1-1 (10.0 g, 9.0 mmol) was dissolved in methylene chloride (MC) (4.0 L) in a flask. Silver trifluoromethanesulfonate (AgOTf) (5.0 g, 19.0 mmol) dissolved in MeOH (400.0 mL) was slowly added thereto and the mixture was stirred at room temperature for 12 hrs. After completing the reaction, the reaction mixture was filtered and the filtrate was dried to obtain compound 1-2 (12.0 g, 94 %).
Preparation of compound 1-3
2-Bromopyridine (10.0 g, 63.0 mmol), dibenzo[b,d]furan-4-yl boronic acid (16.0 g, 76.0 mmol), tetrakis(triphenylphosphine)palladium(O) [Pd(PPh3)4] (2.2 g, 2.0 mmol), Na2CO3 (20.0 g, 19.0 mmol), toluene (300.0 mL), ethanol (EtOH) (150.0 mL), and H2O (10.0 mL) in a flask were stirred at 100°C for 2 hrs. After completing the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (EA). The remaining moisture was removed by using MgSO4 and the mixture was distilled under reduced pressure. By column chromatography with MC/hexane (Hx) = 1/3, compound 1-3 (10.0 g, 63 %) was obtained as white solid.
Preparation of compound D-2
MeOH (200.0 mL) and EtOH (100.0 mL) were added to compound 1-3 (7.0 g, 28.0 mmol) and compound 1-2 (10.0 g, 14.0 mmol) in a flask and the mixture was stirred under reflux for 12 hrs. After completing the reaction, the mixture was cooled to room temperature and filtered. By column chromatography with chloroform (CHCl3), compound D-2 (2.0 g, 17 %) was obtained.
MP 400°C or higher, UV 292nm, PL 525nm, LC 99.06%
Example 2: Preparation of compound D-3
Figure PCTKR2014008963-appb-I000072
Figure PCTKR2014008963-appb-I000073
Preparation of compound 2-1
2-Bromo-5-methylpyridine (15.0 g, 87.0 mmol), phenylboronic acid (14.0 g, 114.0 mmol), Pd(PPh3)4 (3.0 g, 2.6 mmol), K2CO3 (36.0 g, 260.0 mmol), toluene (300.0 mL), EtOH (150.0 mL), and H2O (130.0 mL) in a flask were stirred at 100°C for 3 hrs. After completing the reaction, the mixture was extracted with EA, the remaining moisture was removed by using MgSO4 and the mixture was distilled under reduced pressure. By column chromatography with MC/Hx = 1/2, compound 2-1 (10.0 g, 68 %) was obtained as white solid.
Preparation of compound 2-2
Compound 2-1 (10.0 g, 30.0 mmol), IrCl3·xH2O (8.0 g, 27.0 mmol), 2-ethoxyethanol (200.0 mL), and H2O (70.0 mL) in a flask were stirred at 140°C for 24 hrs. After completing the reaction, the mixture was cooled to room temperature, washed with H2O and MeOH, and dried to obtain compound 2-2 (11.0 g, 75 %).
Preparation of compound 2-3
Compound 2-2 (11.0 g, 10.0 mmol) was dissolved in MC (4.0 L) in a flask. AgOTf (5.0 g, 20.0 mmol) dissolved in MeOH (400.0 mL) was slowly added thereto and the mixture was stirred at room temperature for 12 hrs. After completing the reaction, the reaction mixture was filtered and the filtrate was dried to obtain compound 2-3 (13.0 g, 89 %).
Preparation of compound D-3
MeOH (200.0 mL) and EtOH (100.0 mL) were added to compound 1-3 (7.0 g, 28.0 mmol) and compound 2-3 (10.0 g, 14.0 mmol) in a flask and the mixture was stirred under reflux for 12 hrs. After completing the reaction, the mixture was cooled to room temperature and filtered. By column chromatography with CHCl3, compound D-3 (3.5 g, 33 %) was obtained.
MP 400°C or higher, UV 292nm, PL 527nm, LC 99.19%
Example 3: Preparation of compound D-95
Figure PCTKR2014008963-appb-I000074
Preparation of compound 3-1
2-Bromo-4-methylpyridine (10.0 g, 63.0 mmol), dibenzo[b,d]furan-4-yl boronic acid (15.0 g, 76.0 mmol), Pd(PPh3)4 (2.2 g, 2.0 mmol), Na2CO3 (20.0 g, 19.0 mmol), toluene (300.0 mL), EtOH (150.0 mL), and H2O (10.0 mL) in a flask were stirred at 100°C for 2 hrs. After completing the reaction, the mixture was cooled to room temperature and extracted with EA. The remaining moisture was removed by using MgSO4 and the mixture was distilled under reduced pressure. By column chromatography with MC/Hx = 1/3, compound 3-1 (11.0 g, 67 %) was obtained as white solid.
Preparation of compound D-95
MeOH (200.0 mL) and EtOH (100.0 mL) were added to compound 3-1 (7.0 g, 28.0 mmol) and compound 2-3 (10.0 g, 14.0 mmol) in a flask and the mixture was stirred under reflux for 12 hrs. After completing the reaction, the mixture was cooled to room temperature and filtered. By column chromatography with CHCl3, compound D-95 (1.5 g, 15 %) was obtained.
MP 400°C or higher, UV 292nm, PL 519nm, LC 99.12%
Example 4: Preparation of compound D-96
Figure PCTKR2014008963-appb-I000075
Preparation of compound 4-1
2-Bromo-5-methylpyridine (10.0 g, 63.0 mmol), dibenzo[b,d]furan-4-yl boronic acid (15.0 g, 76.0 mmol), Pd(PPh3)4 (2.2 g, 2.0 mmol), Na2CO3 (20.0 g, 19.0 mmol), toluene (300.0 mL), EtOH (150.0 mL), and H2O (10.0 mL) in a flask were stirred at 100°C for 2 hrs. After completing the reaction, the mixture was cooled to room temperature and extracted with EA. The remaining moisture was removed by using MgSO4 and the mixture was distilled under reduced pressure. By column chromatography with MC/Hx = 1/3, compound 4-1 (13.0 g, 80 %) was obtained as white solid.
Preparation of compound D-96
MeOH (200.0 mL) and EtOH (100.0 mL) were added to compound 4-1 (7.0 g, 28.0 mmol) and compound 2-3 (10.0 g, 14.0 mmol) in a flask and stirred for 12 hrs. After completing the reaction, the mixture was cooled to room temperature and filtered. By column chromatography with CHCl3, compound D-96 (3.0 g, 30 %) was obtained.
MP 390°C, UV 290nm, PL 521nm, LC 96.31%
Example 5: Preparation of compound H-33
Figure PCTKR2014008963-appb-I000076
Preparation of compound 5-1
1-Bromo-2-nitrobenzene (39.0 g, 0.19 mol), dibenzo[b,d]furan-4-yl boronic acid (45.0 g, 0.21 mol), Pd(PPh3)4 (11.1 g, 0.0096 mol), aqueous solution of 2M K2CO3 (290.0 mL), EtOH (290.0 mL), and toluene (580.0 mL) were mixed in a flask, heated to 120°C and stirred for 4 hrs. After completing the reaction, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by using a rotary evaporator. The organic layer was purified by column chromatography to obtain compound 5-1 (47.0 g, 85 %).
Preparation of compound 5-2
Compound 5-1 (47.0 g, 0.16 mol), triethylphosphite (600.0 mL), and 1,2-dichlorobenzene (300.0 mL) were mixed in a flask, heated to 150°C and stirred for 12 hrs. After completing the reaction, the unreacted triethylphosphite and 1,2-dichlorobenzene were removed by using a distillation device. The mixture was washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by using a rotary evaporator. The organic layer was purified by column chromatography to obtain compound 5-2 (39.0 g, 81 %).
Preparation of compound H-33
NaH (1.9 mg, 42.1 mmol) was dissolved in dimethylformamide (DMF) in a flask and the mixture was stirred. Compound 5-2 (7.0 g, 27.2 mmol) was dissolved in DMF in a flask and added to the stirred NaH solution, and the mixture was stirred for 1 hr. 2-Chloro-4,6-diphenylpyrimidine (8.7 g, 32.6 mmol) was dissolved in DMF in a flask and stirred. The mixture stirred for 1 hr was added thereto and then stirred at room temperature for 24 hrs. After completing the reaction, the resulting solid was filtered, washed with EA, and purified by column chromatography to obtain compound H-33 (3.5 g, 25 %).
Example 6: Preparation of compound H-45
Figure PCTKR2014008963-appb-I000077
Preparation of compound 6-1
By using dibenzo[b,d]thiophene-4-yl boronic acid (10.0 g, 43.84 mmol) and the same method as Preparation of compound 3-1, compound 6-1 (10.0 g, 32.74 mmol, 74.68 %) was obtained.
Preparation of compound 6-2
By using compound 6-1 (10.0 g, 32.74 mmol) and the same method as Preparation of compound 5-2, compound 6-2 (7.0 g, 25.60 mmol, 78.19 %) was obtained.
Preparation of compound H-45
By using compound 6-2 (7.0 g, 25.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.7 g, 32.6 mmol), and the same method as Preparation of compound H-33, compound H-45 (5.6 g, 40.0 %) was obtained.
Example 7: Preparation of compound H-60
Figure PCTKR2014008963-appb-I000078
By using compound 6-2 (7.0 g, 25.6 mmol) and compound 7-1 (8.2 g, 32.6 mmol), and the same method as Preparation of compound H-33, compound H-60 (5.3 g, 49.0 %) was obtained.
Example 8: Preparation of compound H-110
Figure PCTKR2014008963-appb-I000079
Preparation of compound 8-1
2-Bromo-9,9-dimethyl-9H-fluorene (80.0 g, 291.0 mmol), 2-chlorobenzenamine (45.0 mL, 437.0 mmol), palladium(II) acetate [Pd(OAc)2] (2.6 g, 12.0 mmol), tri-tert-butylphosphine [P(t-Bu)3] (12.0 mL, 24.0 mmol), sodium tert-butoxide (NaOt-Bu) (70.0 g, 728.0 mmol), and toluene (800.0 mL) were mixed in a flask, heated to 120°C and stirred for 9 hrs. After completing the reaction, the mixture was cooled to room temperature, extracted with EA (1.5 L). The obtained organic layer was washed with distilled water (400.0 mL). Then, the solvent was removed under reduced pressure and the obtained solid was washed with hexane, filtered and dried. After the separation via column chromatography on silica gel and recrystallization of the solid, compound 8-1 (70.0 g, 75 %) was obtained.
Preparation of compound 8-2
Compound 8-1 (70.0 g, 218.0 mmol), Pd(OAc)2 (2.4 g, 11.0 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3HBF4) (8.0 g, 22.0 mmol), Na2CO3 (70.0 g, 654.0 mmol), and dimethylacetamide (DMA) (1.2 L) were mixed in a flask and stirred at 190°C for 3 hrs. After completing the reaction, the mixture was extracted with EA (1.0 L), and the obtained organic layer was washed with distilled water (200.0 mL) and dried over anhydrous MgSO4. The organic solvent was removed under reduced pressure. After the separation of the obtained solid via column chromatography on silica gel and recrystallization, compound 8-2 (22.0 g, 36 %) was obtained.
Preparation of compound 8-3
Compound 8-2 (15.0 g, 53.0 mmol), 1,4-dibromobenzene (32.0 mL, 265.0 mmol), Pd(OAc)2 (1.2 g, 5.0 mmol), P(t-Bu)3 (30.0 mL, 64.0 mmol), NaOt-Bu (25.0 g, 265.0 mmol), and toluene (300.0 mL) were mixed in a flask and stirred at 120°C for 24 hrs. After completing the reaction, the mixture was cooled to room temperature and extracted with EA (1.5 L). The obtained organic layer was washed with distilled water (400.0 mL). The solvent was removed under reduced pressure, and the obtained solid was washed with hexane, filtered and dried. After the separation via column chromatography on silica gel and recrystallization, compound 8-3 (7.0 g, 30 %) was obtained.
Preparation of compound 8-4
Compound 8-3 (7.0 g, 16.0 mmol) was dissolved in tetrahydrofuran (THF) (100.0 mL) in a flask and n-butyllithium (n-BuLi) (2.5 M in hexane, 10.0 mL, 24.0 mmol) was added thereto at -78 °C. After stirring the mixture at -78 °C for 1 hr, boron tri-isopropoxide [B(Oi-Pr)3] (6.0 mL, 24.0 mmol) was added thereto. The mixture was stirred for 2 hrs and the reaction was completed by using aqueous ammonium chloride solution (20.0 mL). The mixture was extracted with EA (500.0 mL), and the obtained organic layer was washed with distilled water (200.0 mL) and dried over anhydrous MgSO4. The organic solvent was removed under reduced pressure. After the separation of the obtained solid via recrystallization, compound 8-4 (5.0 g, 75 %) was obtained.
Preparation of compound H-110
2-Chloro-4,6-diphenyl-1,3,5-triazine (6.5 g, 0.03 mol), compound 8-4 (19.2 g, 0.036 mol), Pd(PPh3)4 (1.6 g, 0.001 mol), K2CO3 (11.0 g, 0.08 mol), toluene (140.0 mL), EtOH (35.0 mL), and H2O (40.0 mL) in a flask were stirred at 120°C for 12 hrs. After completing the reaction, the mixture was extracted with EA, and the obtained organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure and the product was separated via column chromatography to obtain compound H-110 (5.7 g, 27 %).
Example 9: Preparation of compound H-135
Figure PCTKR2014008963-appb-I000080
After adding o-xylene (110.0 mL) to 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (3.65 g, 10.9 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.9 g, 12.6 mmol), Pd(OAc)2 (0.12 g, 0.55 mmol), S-phos (2-dicyclophosphino-2’, 6’-dimethoxybiphenyl) (0.45 g, 1.1 mmol), and NaOt-Bu (2.6 g, 27.4 mmol) in a flask, the mixture was stirred under reflux for a day. After completing the reaction, the mixture was cooled to room temperature and extracted with distilled water and EA. The obtained organic layer was distilled under reduced pressure. By column chromatography with MC/Hx, compound H-135 (3.7 g, 52 %) was obtained.
Example 10: Preparation of compound H-176
Figure PCTKR2014008963-appb-I000081
Preparation of compound 10-1
After adding 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (10.0 g, 30.1 mmol), 1-bromo-3-iodobenzene (12.8 g, 45.1 mmol), CuI (2.9 g, 15.05 mmol), ethylenediamine (EDA) (2.0 mL, 30.1 mmol), and K3PO4 (16.0 g, 75.25 mmol) to toluene (150.0 mL) in a flask, the mixture was stirred under reflux for a day. The mixture was extracting with MC and distilled under reduced pressure. By column chromatography with MC/Hx, compound 10-1 (13.2 g, 87 %) was obtained.
Preparation of compound 10-2
Compound 10-1 (13.2 g, 27.1 mmol), bis(triphenylphosphine)palladium(II) dichloride [PdCl2(PPh3)2] (0.95 g, 1.35 mmol), bis(pinacolato)diboron (8.25 g, 32.5 mmol), potassium acetate (KOAc) (5.3 g, 54.2 mmol), and 1,4-dioxane (140.0 mL) in a flask were stirred at 120°C for a day. After completing the reaction, the mixture was washed with distilled and extracted with MC. The obtained organic layer was dried over MgSO4 and distilled under reduced pressure to remove the solvent. By the purification via column chromatography, compound 10-2 (8.5 g, 59 %) was obtained.
Preparation of compound H-176
After adding toluene (48.0 mL), EtOH (6.0 mL), and distilled water (12.0 mL) to compound 10-2 (5.0 g, 9.36 mmol), triazine (3.5 g, 10.3 mmol), Pd(PPh3)4 (0.54 g, 0.5 mmol), and K2CO3 (3.2 g, 23.4 mmol) in a flask, the mixture was stirred under reflux for a day. After completing the reaction, the mixture was cooled to room temperature and extracted with distilled water and EA. The obtained organic layer was distilled under reduced pressure. By column chromatography with MC/Hx, compound H-176 (4.3 g, 64 %) was obtained.
The data of the dopant compounds prepared in Examples 5 to 8 and other dopant compounds which can be easily prepared from said Examples are provided in the Table 1 below:
Table 1
Figure PCTKR2014008963-appb-I000082
Figure PCTKR2014008963-appb-I000083
Device Example 1: Production of an OLED device by using the organic
electroluminescent compound according to the present invention
An organic light-emitting diode (OLED) device comprising the light-emitting material of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1’-([1,1’-biphenyl]-4,4’-diyl)bis(N1-(naphthalene-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) 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 the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Compound H-60 was introduced as a host into one cell of the vacuum vapor depositing apparatus, and compound D-3 as a dopant was introduced into another cell. The two materials were evaporated at different rates and the dopant was deposited in a doping amount of 15 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidiazole was introduced into one cell, and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rates and were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed green emission having power efficiency of 44.01 m/W and a luminance of 1620 cd/m2 at 3.6 V.
Device Example 2: Production of an OLED device by using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except that compound H-135 was used as a host and compound D-3 was used as a dopant in a light-emitting material.
The produced OLED device showed green emission having power efficiency of 56.61 m/W and a luminance of 2190 cd/m2 at 2.6 V.
Device Example 3: Production of an OLED device by using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except that compound H-176 was used as a host and compound D-3 was used as a dopant in a light-emitting material.
The produced OLED device showed green emission having power efficiency of 51.91 m/W and a luminance of 2510 cd/m2 at 2.6 V.
Device Example 4: Production of an OLED device by using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except that compound H-135 was used as a host and compound D-96 was used as a dopant in a light-emitting material.
The produced OLED device showed green emission having power efficiency of 47.71 m/W and a luminance of 3140 cd/m2 at 2.6 V.
Comparative Example 1: Production of an OLED device by using
conventional light-emitting materials
An OLED device was produced in the same manner as in Device Example 1, except that comparative compound 1 was used as a hostand compound D-2 was used as a dopant in a light-emitting material; a light-emitting layer having a thickness of 30 nm is formed on the hole transport layer; and 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene having a thickness of 10 nm as a hole blocking layer is formed.
The produced OLED device showed green emission having power efficiency of 16.81 m/W and a luminance of 3000 cd/m2 at 6.9 V.
Comparative Compound 1
Figure PCTKR2014008963-appb-I000084
The organic electroluminescent compound of the present invention provides higher luminance efficiency and power efficiency at lower driving voltage than the device comprising conventional light-emitting materials by comprising a combination of specific dopant and host compounds in a light-emitting layer, and thus improves consumption power.

Claims (8)

  1. A combination of at least one dopant compound represented by the following formula 1 and at least one host compound represented by the following formula 2:
    Figure PCTKR2014008963-appb-I000085
    wherein
    L1 to L3 are each independently selected from the following structures, with the proviso that at least one of L1 to L3 represents A-1, A-2 or A-3:
    Figure PCTKR2014008963-appb-I000086
    X represents O or S;
    R1 to R11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; and
    a to h each independently represent an integer of 0 to 4; where a to h is an integer of 2 or more, each of R1 to each of R8 is the same or different.
    wherein
    Y1 represents O, S, NR31 or CR32R33;
    L4 represents a single bond, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
    R21 to R23 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 5- to 30-membered heteroaryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amino group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group containing a nitrogen atom;
    R31 to R33 each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    m and o each independently represent an integer of 0 to 4; where m or o is an integer of 2 or more, each of R21 or each of R23 is the same or different;
    n represents an integer of 0 to 2; where n is 2, each of R22 is the same or different; and
    the heteroaryl group contains at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
  2. The combination according to claim 1, wherein R1 to R11 in the compound of formula 1 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C3-C10)cycloalkyl group, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group, and in the compound of formula 2, L4 represents a single bond, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group, R21 to R23 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted silyl group, and Ar1 represents a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group containing a nitrogen atom.
  3. The combination according to claim 1, wherein the compound of formula 1 is represented by the following formula 3, 4 or 5:
    Figure PCTKR2014008963-appb-I000088
    Figure PCTKR2014008963-appb-I000089
    Figure PCTKR2014008963-appb-I000090
    wherein
    R1 to R6, a to f, X, L2 and L3 are as defined in claim 1.
  4. The combination according to claim 1, wherein the compound of formula 2 is represented by one of the following formulae 6 to 11:
    Figure PCTKR2014008963-appb-I000091
    Figure PCTKR2014008963-appb-I000092
    Figure PCTKR2014008963-appb-I000093
    Figure PCTKR2014008963-appb-I000094
    Figure PCTKR2014008963-appb-I000095
    Figure PCTKR2014008963-appb-I000096
    wherein
    R21 to R23, Y1, L4, Ar1, m, n and o are as defined in claim 1.
  5. The combination according to claim 2, wherein the compound of formula 3 is selected from the group consisting of the following structures:
    Figure PCTKR2014008963-appb-I000097
    Figure PCTKR2014008963-appb-I000098
    Figure PCTKR2014008963-appb-I000099
    Figure PCTKR2014008963-appb-I000100
    Figure PCTKR2014008963-appb-I000101
    Figure PCTKR2014008963-appb-I000102
    Figure PCTKR2014008963-appb-I000103
    Figure PCTKR2014008963-appb-I000104
    Figure PCTKR2014008963-appb-I000105
    Figure PCTKR2014008963-appb-I000106
    Figure PCTKR2014008963-appb-I000107
    Figure PCTKR2014008963-appb-I000108
    Figure PCTKR2014008963-appb-I000109
    Figure PCTKR2014008963-appb-I000110
    Figure PCTKR2014008963-appb-I000111
    Figure PCTKR2014008963-appb-I000112
    Figure PCTKR2014008963-appb-I000113
    Figure PCTKR2014008963-appb-I000114
    Figure PCTKR2014008963-appb-I000115
    Figure PCTKR2014008963-appb-I000116
  6. The combination according to claim 2, wherein the compound of formula 4 is selected from the group consisting of the following structures:
    Figure PCTKR2014008963-appb-I000117
    Figure PCTKR2014008963-appb-I000118
    Figure PCTKR2014008963-appb-I000119
    Figure PCTKR2014008963-appb-I000120
    Figure PCTKR2014008963-appb-I000121
    Figure PCTKR2014008963-appb-I000122
    Figure PCTKR2014008963-appb-I000123
    Figure PCTKR2014008963-appb-I000124
  7. The combination according to claim 2, wherein the compound of formula 5 is selected from the group consisting of the following structures:
    Figure PCTKR2014008963-appb-I000125
    Figure PCTKR2014008963-appb-I000126
    Figure PCTKR2014008963-appb-I000127
    Figure PCTKR2014008963-appb-I000128
    Figure PCTKR2014008963-appb-I000129
    Figure PCTKR2014008963-appb-I000130
  8. The combination according to claim 3, wherein the compounds of formulae 6 to 11 are selected from the group consisting of the following structures:
    Figure PCTKR2014008963-appb-I000131
    Figure PCTKR2014008963-appb-I000132
    Figure PCTKR2014008963-appb-I000133
    Figure PCTKR2014008963-appb-I000134
    Figure PCTKR2014008963-appb-I000135
    Figure PCTKR2014008963-appb-I000136
    Figure PCTKR2014008963-appb-I000137
    Figure PCTKR2014008963-appb-I000138
    Figure PCTKR2014008963-appb-I000139
    Figure PCTKR2014008963-appb-I000140
    Figure PCTKR2014008963-appb-I000141
    Figure PCTKR2014008963-appb-I000142
    Figure PCTKR2014008963-appb-I000143
    Figure PCTKR2014008963-appb-I000144
    Figure PCTKR2014008963-appb-I000145
    Figure PCTKR2014008963-appb-I000146
    Figure PCTKR2014008963-appb-I000147
    Figure PCTKR2014008963-appb-I000148
    Figure PCTKR2014008963-appb-I000149
    Figure PCTKR2014008963-appb-I000150
    Figure PCTKR2014008963-appb-I000151
    Figure PCTKR2014008963-appb-I000152
    Figure PCTKR2014008963-appb-I000153
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