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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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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PCT/KR2014/008963
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French (fr)
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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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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201480050614.9A priority Critical patent/CN105531349A/zh
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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    • 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
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    • 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 C07D451/00ย -ย 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 C07D451/00ย -ย 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
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    • 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-(2โ€™-benzothienyl)-pyridinato-N,C3โ€™)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.
  • 4,4โ€™-N,Nโ€™-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 โ€œsubstituted or unsubstitutedโ€ 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 โ‡ X โ‡ 2), AlO X (1 โ‡ X โ‡ 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 120ยฐC 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 โ‡ /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 1โ€™ -([1,1โ€™-biphenyl]-4,4โ€™-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,Nโ€™-di(4-biphenyl)-N,Nโ€™-di(4-biphenyl)-4,4โ€™-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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  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2014/008963 2013-09-26 2014-09-25 A combination of a host compound and a dopant compound WO2015046916A1 (en)

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TW201605841A (zh) 2016-02-16
CN105531349A (zh) 2016-04-27
KR20150034333A (ko) 2015-04-03
KR102158000B1 (ko) 2020-09-22

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