WO2015046916A1 - Combinaison d'un composé hôte et d'un composé dopant - Google Patents

Combinaison d'un composé hôte et d'un composé dopant Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
compound
group
mmol
Prior art date
Application number
PCT/KR2014/008963
Other languages
English (en)
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
Original Assignee
Rohm And Haas Electronic Materials Korea Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN201480050614.9A priority Critical patent/CN105531349A/zh
Publication of WO2015046916A1 publication Critical patent/WO2015046916A1/fr

Links

Classifications

    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • 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.

Abstract

La présente invention concerne une combinaison spécifique de composés dopants et de composés hôtes. En utilisant une combinaison de composés dopants et de composés hôtes selon la présente invention, un dispositif organique électroluminescent présente une meilleure efficacité de courant par rapport à celle d'un matériau d'émission de lumière classique, et donc une meilleure efficacité de puissance au niveau d'une tension de commande faible.
PCT/KR2014/008963 2013-09-26 2014-09-25 Combinaison d'un composé hôte et d'un composé dopant WO2015046916A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480050614.9A CN105531349A (zh) 2013-09-26 2014-09-25 主体化合物和掺杂剂化合物的组合

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2013-0114260 2013-09-26
KR1020130114260A KR102158000B1 (ko) 2013-09-26 2013-09-26 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2015046916A1 true WO2015046916A1 (fr) 2015-04-02

Family

ID=52743944

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/008963 WO2015046916A1 (fr) 2013-09-26 2014-09-25 Combinaison d'un composé hôte et d'un composé dopant

Country Status (4)

Country Link
KR (1) KR102158000B1 (fr)
CN (1) CN105531349A (fr)
TW (2) TW201605841A (fr)
WO (1) WO2015046916A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015190789A1 (fr) * 2014-06-09 2015-12-17 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
US20160155962A1 (en) * 2014-11-28 2016-06-02 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
WO2016186321A1 (fr) * 2015-05-19 2016-11-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant
WO2017025164A1 (fr) * 2015-08-11 2017-02-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
CN106699753A (zh) * 2015-07-14 2017-05-24 上海和辉光电有限公司 一种化合物及其应用
WO2017200210A1 (fr) * 2016-05-17 2017-11-23 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
CN107531716A (zh) * 2015-05-19 2018-01-02 罗门哈斯电子材料韩国有限公司 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置
JP2018520513A (ja) * 2015-06-26 2018-07-26 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 多成分ホスト材料及びそれを含む有機電界発光デバイス
US10199584B2 (en) 2016-08-10 2019-02-05 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
JP2019519096A (ja) * 2016-05-17 2019-07-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物、有機電界発光材料、及びそれを含む有機電界発光デバイス
US10930853B2 (en) 2015-11-26 2021-02-23 Samsung Display Co., Ltd. Organic light-emitting device
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) * 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11427607B2 (en) * 2014-05-02 2022-08-30 Universal Display Corporation Organic electroluminescent materials and devices
US11621397B2 (en) 2018-01-17 2023-04-04 Lg Chem, Ltd. Iridium complexes containing a ligand including a (dibenzo [B,D] furanyl) pyridine skeleton having deuterium substitutions para and meta to the N ring atom and organic light emitting device comprising the same
US11696499B2 (en) 2016-05-10 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
US11910707B2 (en) 2015-12-23 2024-02-20 Samsung Display Co., Ltd. Organic light-emitting device

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102643060B1 (ko) * 2016-03-28 2024-03-04 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102063664B1 (ko) * 2016-05-17 2020-01-08 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
CN107488182B (zh) * 2016-06-09 2020-07-28 株式会社Lg化学 化合物及利用它的有机发光元件
CN106117117B (zh) * 2016-06-24 2018-05-18 中节能万润股份有限公司 一种含有卤素的芴基苯并吲哚衍生物的制备方法
CN106397415A (zh) * 2016-08-31 2017-02-15 江苏三月光电科技有限公司 一种基于氮杂苯的五元环取代化合物及其应用
KR102529341B1 (ko) * 2016-10-05 2023-05-09 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2018123783A1 (fr) * 2016-12-27 2018-07-05 新日鉄住金化学株式会社 Matériau pour élément électroluminescent organique et élément électroluminescent organique
KR20180098809A (ko) 2017-02-27 2018-09-05 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR102129508B1 (ko) * 2017-07-14 2020-07-02 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
CN109326741A (zh) * 2017-08-01 2019-02-12 江苏三月光电科技有限公司 一种含有氮杂苯类化合物的有机发光器件
CN107586299A (zh) * 2017-09-29 2018-01-16 江苏三月光电科技有限公司 一种以氮杂苯为核心的有机化合物及其应用
CN109970623B (zh) * 2017-12-28 2021-01-12 武汉尚赛光电科技有限公司 三芳胺类衍生物及其制备方法、应用和器件
CN108047235B (zh) * 2017-12-29 2019-10-18 西安瑞联新材料股份有限公司 一种芳香族杂环化合物及其应用
KR102184860B1 (ko) * 2018-05-14 2020-12-01 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN111527096B (zh) * 2018-05-14 2023-10-27 株式会社Lg化学 化合物及包含其的有机发光器件
CN109096291B (zh) * 2018-08-22 2022-05-20 宇瑞(上海)化学有限公司 一种含二取代基吲哚并杂环化合物的有机光电器件及其应用
CN109400590A (zh) * 2018-11-21 2019-03-01 苏州大学 一种热活化延迟荧光材料及其在有机发光二极管中的应用
CN110041376B (zh) * 2019-06-06 2021-10-29 江西师范大学 一种环金属铱配合物及其制备方法和应用
KR20210063747A (ko) 2019-11-25 2021-06-02 삼성전자주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물
KR20210143652A (ko) * 2020-05-20 2021-11-29 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
CN113816996A (zh) * 2020-06-20 2021-12-21 北京夏禾科技有限公司 一种磷光有机金属配合物及其应用
CN113816997A (zh) 2020-06-20 2021-12-21 北京夏禾科技有限公司 一种磷光有机金属配合物及其应用
CN111808142A (zh) * 2020-07-09 2020-10-23 奥来德(上海)光电材料科技有限公司 一种有机磷发光化合物及其制备方法和应用
CN114516890A (zh) * 2020-11-18 2022-05-20 北京夏禾科技有限公司 有机电致发光材料及其器件
CN114907413A (zh) * 2021-02-06 2022-08-16 北京夏禾科技有限公司 有机电致发光材料及其器件
CN114075203B (zh) * 2021-06-17 2023-06-13 陕西莱特迈思光电材料有限公司 一种有机化合物以及使用其的有机电致发光器件和电子装置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130119354A1 (en) * 2011-11-15 2013-05-16 Universal Display Corporation Heteroleptic iridium complex

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8062769B2 (en) * 2006-11-09 2011-11-22 Nippon Steel Chemical Co., Ltd. Indolocarbazole compound for use in organic electroluminescent device and organic electroluminescent device
KR101511072B1 (ko) * 2009-03-20 2015-04-10 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130119354A1 (en) * 2011-11-15 2013-05-16 Universal Display Corporation Heteroleptic iridium complex

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TSUJIMOTO., H. ET AL.: "Photoluminescent properties of heteroleptic cyclometalated platinum(II) complexes bearing 1,3-bis(3,4-dibutoxyphenyl)propane-1,3-dionate as an ancillary ligand", JOURNAL OF LUMINESCENCE, vol. 130, 2010, pages 217 - 221 *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11919916B2 (en) 2014-05-02 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11427607B2 (en) * 2014-05-02 2022-08-30 Universal Display Corporation Organic electroluminescent materials and devices
WO2015190789A1 (fr) * 2014-06-09 2015-12-17 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
US20160155962A1 (en) * 2014-11-28 2016-06-02 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
CN107531716A (zh) * 2015-05-19 2018-01-02 罗门哈斯电子材料韩国有限公司 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置
CN107531716B (zh) * 2015-05-19 2021-06-22 罗门哈斯电子材料韩国有限公司 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置
JP2018517679A (ja) * 2015-05-19 2018-07-05 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド リンホスト材料及びそれを含む有機電界発光素子
JP7127095B2 (ja) 2015-05-19 2022-08-29 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド リンホスト材料及びそれを含む有機電界発光素子
JP2021022739A (ja) * 2015-05-19 2021-02-18 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド リンホスト材料及びそれを含む有機電界発光素子
WO2016186321A1 (fr) * 2015-05-19 2016-11-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant
JP2018520513A (ja) * 2015-06-26 2018-07-26 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 多成分ホスト材料及びそれを含む有機電界発光デバイス
CN106699753A (zh) * 2015-07-14 2017-05-24 上海和辉光电有限公司 一种化合物及其应用
WO2017025164A1 (fr) * 2015-08-11 2017-02-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US10930853B2 (en) 2015-11-26 2021-02-23 Samsung Display Co., Ltd. Organic light-emitting device
US11856842B2 (en) 2015-11-26 2023-12-26 Samsung Display Co., Ltd. Organic light-emitting device
US11910707B2 (en) 2015-12-23 2024-02-20 Samsung Display Co., Ltd. Organic light-emitting device
US11696499B2 (en) 2016-05-10 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
JP2019519096A (ja) * 2016-05-17 2019-07-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物、有機電界発光材料、及びそれを含む有機電界発光デバイス
WO2017200210A1 (fr) * 2016-05-17 2017-11-23 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, matériau organique électroluminescent et dispositif organique électroluminescent les comprenant
US10199584B2 (en) 2016-08-10 2019-02-05 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11711968B2 (en) 2016-10-07 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11621397B2 (en) 2018-01-17 2023-04-04 Lg Chem, Ltd. Iridium complexes containing a ligand including a (dibenzo [B,D] furanyl) pyridine skeleton having deuterium substitutions para and meta to the N ring atom and organic light emitting device comprising the same
US11217757B2 (en) * 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11700766B2 (en) 2018-03-12 2023-07-11 Universal Display Corporation Host materials for electroluminescent devices

Also Published As

Publication number Publication date
TW201605841A (zh) 2016-02-16
KR102158000B1 (ko) 2020-09-22
CN105531349A (zh) 2016-04-27
TW201527298A (zh) 2015-07-16
KR20150034333A (ko) 2015-04-03

Similar Documents

Publication Publication Date Title
WO2015046916A1 (fr) Combinaison d'un composé hôte et d'un composé dopant
WO2018105888A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
EP3446345A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant
EP3494117A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2018021841A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2015084021A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
EP2875094A1 (fr) Nouvelle combinaison d'un composé hôte et d'un composé dopant et dispositif électroluminescent organique la comprenant
WO2014185751A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP2875093A1 (fr) Nouvelle combinaison d'un composé hôte et d'un composé dopant et un dispositif électroluminescent organique la comprenant
WO2015037965A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2015056993A1 (fr) Combinaison d'un composé hôte et d'un composé dopant et dispositif électroluminescent organique comprenant la combinaison.
WO2015099486A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
WO2015009076A1 (fr) Combinaison d'un composé dopant et d'un composé hôte et dispositif électroluminescent organique comprenant ladite combinaison
WO2013109045A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2014129846A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique comprenant ces composés
WO2013154325A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
EP2817387A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP2828254A1 (fr) Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique les comprenant
EP3201200A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2015093878A1 (fr) Composé électroluminescent organique, et matériau hôte à composants multiples et dispositif électroluminescent organique comprenant ledit composé
WO2013073859A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent comprenant lesdits composés
WO2014003440A1 (fr) Nouvelle combinaison d'un composé hôte et d'un composé dopant et dispositif électroluminescent organique la comprenant
WO2017183859A1 (fr) Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant
WO2014104704A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2014042405A1 (fr) Nouvelle combinaison d'un composé hôte et d'un composé dopant et dispositif à électroluminescence organique les comprenant

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201480050614.9

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14849772

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14849772

Country of ref document: EP

Kind code of ref document: A1