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WO2021025433A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2021025433A1
WO2021025433A1 PCT/KR2020/010271 KR2020010271W WO2021025433A1 WO 2021025433 A1 WO2021025433 A1 WO 2021025433A1 KR 2020010271 W KR2020010271 W KR 2020010271W WO 2021025433 A1 WO2021025433 A1 WO 2021025433A1
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group
layer
electron transport
aryl
auxiliary layer
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한송이
박호철
김영모
송효범
정승은
김근형
김태형
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Solus Advanced Materials Co Ltd
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    • 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
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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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
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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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
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    • 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
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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present invention is an organic electroluminescent device that simultaneously exhibits high luminous efficiency, low driving voltage, and long life by separately providing an organic functional layer in which the material of the light-emitting layer and the material of the electron-transport auxiliary layer are mixed between the light-emitting layer and the auxiliary layer for transporting electrons. Can provide.
  • the introduction of a multi-layered structure improves the performance of organic EL devices to the commercialization characteristics, and is trying to expand its application range to portable information display devices and TV display devices, starting with radio display products for vehicles in 1997.
  • the organic EL device when a current or voltage is applied to two electrodes, holes are injected into the organic material layer from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and these excitons fall to the ground state to emit light.
  • the organic EL device may be classified into a fluorescent EL device in which singlet excitons contribute to light emission and a phosphorescent EL device in which triplet excitons contribute to light emission according to the type of electron spin of the formed excitons.
  • the electron spin of excitons which is formed by recombination of electrons and holes, generates singlet excitons and triplet excitons at a rate of 25% and 75%.
  • Fluorescent EL devices that emit light by singlet excitons theoretically cannot exceed 25% of the internal quantum efficiency depending on the generation rate, and 5% of the external quantum efficiency is accepted as a limit.
  • Phosphorescent EL devices that emit light by triplet excitons improve luminous efficiency up to 4 times compared to fluorescence when a metal complex compound containing heavy atoms of transition metals such as Ir and Pt is used as a phosphorescent dopant. I can make it.
  • phosphorescent EL devices exhibit higher luminous efficiency than fluorescence in terms of luminous efficiency based on theoretical facts, but in blue phosphorescent devices excluding green and red, a phosphorescent dopant with deep blue color purity and high efficiency and a wide energy satisfying the same Blue phosphorescent devices have not yet been commercialized due to insufficient development level for Gap hosts, and blue phosphorescent devices are being used in products.
  • the present invention was devised to solve the above-described problem, and by separately providing an organic functional layer in which a light emitting layer material and an electron transport auxiliary layer material are mixed in a predetermined ratio between the light emitting layer and the electron transport auxiliary layer, high efficiency, low voltage and long lifespan It is a technical problem to provide an organic EL device exhibiting at the same time.
  • the present invention is a positive electrode; Hole transport area; Light-emitting layer; It has a structure in which an electron transport region and a cathode are sequentially stacked, and the electron transport region includes an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and is disposed between the light emitting layer and the electron transport auxiliary layer. Further comprising an organic functional layer, wherein the organic functional layer, the material of the light emitting layer; And a mixture of materials for the electron transport auxiliary layer.
  • the absolute value of the HOMO energy level of the electron transport auxiliary layer may be higher than the absolute value of the HOMO energy level of the emission layer.
  • a difference between the absolute value of the HOMO energy level of the electron transport auxiliary layer and the absolute value of the HOMO energy level of the emission layer may be greater than 0 eV and less than or equal to 1.5 eV.
  • the absolute value of the LUMO energy level of the electron transport auxiliary layer may be lower than the absolute value of the LUMO energy level of the electron transport layer and higher than the absolute value of the LUMO energy level of the light emitting layer.
  • a difference between the absolute value of the LUMO energy level of the electron transport auxiliary layer and the absolute value of the LUMO energy level of the electron transport layer may be greater than 0 eV and less than 1.0 eV.
  • a difference between the absolute value of the LUMO energy level of the electron transport auxiliary layer and the absolute value of the LUMO energy level of the emission layer may be in the range of 0 to 1.0 eV.
  • the organic functional layer is a material of the electron transport auxiliary layer; And it may be formed by co-deposition (co-deposition) the material of the light emitting layer.
  • the organic functional layer includes a material of the electron transport auxiliary layer, a host material and a dopant material contained in the light emitting layer, and the material of the electron transport auxiliary layer and the host material
  • the mixing ratio is 5 to 95: 95 to 5 weight ratio
  • the dopant material may be included in an amount of 0.5 to 30 parts by weight based on the total weight of the material of the electron transport auxiliary layer and the host material.
  • the hole transport region may include at least one of a hole injection layer, a hole transport layer, and a hole transport auxiliary layer.
  • an organic electroluminescent device having a low driving voltage and high luminous efficiency can be provided by arranging an organic functional layer in which these materials are mixed in a predetermined ratio between the light emitting layer and the electron transport auxiliary layer.
  • an organic electroluminescent device of the present invention to a display panel, it is possible to provide a display panel with improved performance and lifespan.
  • FIG. 1 is a cross-sectional view showing the structure of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view showing the structure of an organic electroluminescent device according to another embodiment of the present invention.
  • FIG. 3 is a graph showing a relationship between a high occupied molecular orbital (HOMO) energy level between an emission layer and an electron transport auxiliary layer according to an embodiment of the present invention.
  • HOMO high occupied molecular orbital
  • FIG. 4 is a graph showing a relationship between an LUMO (lowest unoccupied molecular orbital) energy level between a light emitting layer, an electron transport auxiliary layer, and an electron transport layer according to another embodiment of the present invention.
  • LUMO lowest unoccupied molecular orbital
  • An organic electroluminescent device includes: an anode; A negative electrode disposed opposite to the positive electrode; And one or more organic material layers interposed between the anode and the cathode and including a hole transport region, a light emitting layer, and an electron transport region, and between the light emitting layer and the electron transport auxiliary layer included in the electron transport region.
  • the material of the mixture includes an organic functional layer mixed with each other.
  • This organic functional layer is in a state in which two adjacent organic material layers, that is, the material of the light emitting layer and the material of the electron transport auxiliary layer, are mixed and co-depositioned, so electron transport due to the barrier-free effect of the use of the same material. Electrons injected from the auxiliary layer can be smoothly supplied from the organic layer to the emission layer, thereby improving the luminous efficiency of the organic EL device and significantly improving the lifespan characteristics.
  • FIG. 1 is a diagram showing the structure of an organic electroluminescent device according to an embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode 10; A hole transport region 30; A light emitting layer 40; An electron transport region 50 and a cathode 20 are sequentially stacked, and the electron transport region 50 includes an electron transport auxiliary layer 53, an electron transport layer 51, and an electron injection layer 52.
  • the material of the light emitting layer 40 and the material of the electron transport auxiliary layer 53 are mixed in a predetermined ratio, at least one It has a structure including an organic functional layer 60 of.
  • the hole transport region 30 may include at least one of the hole transport layer 31 and the hole injection layer 32.
  • the anode 10 serves to inject holes into the organic material layer (A).
  • the material constituting the anode 10 is not particularly limited, and a conventional material known in the art may be used.
  • Non-limiting examples thereof include metals such as vanadium, chromium, copper, zinc, and gold; Alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al and SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; And carbon black.
  • metals such as vanadium, chromium, copper, zinc, and gold
  • Alloys thereof Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al and S
  • the method of manufacturing the positive electrode 10 is also not particularly limited, and may be manufactured according to a conventional method known in the art. For example, a method of coating an anode material on a substrate made of a silicon wafer, quartz, glass plate, metal plate, or plastic film may be mentioned.
  • the cathode 20 serves to inject electrons into the organic material layer (A).
  • the material forming the cathode 20 is not particularly limited, and a conventional material known in the art may be used.
  • Non-limiting examples thereof include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; Alloys thereof; And multi-layered materials such as LiF/Al and LiO 2 /Al.
  • a method of manufacturing the negative electrode 20 is also not particularly limited, and may be manufactured according to a method known in the art.
  • the organic material layer (A) included in the organic electroluminescent device according to the present invention can be used without limitation in a conventional configuration used as an organic material layer of an existing organic EL device.
  • a hole transport region 30, a light emitting layer 40, and an electron It may include at least one selected from the group consisting of the transport region 50.
  • the hole transport region 30 included in the organic material layer A of the present invention serves to move holes injected from the anode 10 to the emission layer 40.
  • the hole transport region 30 may include at least one selected from the group consisting of a hole injection layer 31 and a hole transport layer 32. In this case, when considering the characteristics of the organic electroluminescent device, it is preferable to include both the hole injection layer 31 and the hole transport layer 32 described above.
  • the material constituting the above-described hole injection layer 31 and the hole transport layer 32 is not particularly limited as long as it is a material having a low hole injection barrier and high hole mobility, and the hole injection layer/transport layer material used in the industry is not limited. Can be used. In this case, the material forming the hole injection layer 31 and the hole transport layer 32 may be the same or different from each other.
  • hole injection material a hole injection material known in the art may be used without limitation.
  • usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4' ,4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2TNATA(4,4',4"-tris(N,-(2 -naphthyl)-N-phenylamino ⁇ -triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA
  • hole transport material a hole transport material known in the art may be used without limitation.
  • usable hole transport materials include carbazole derivatives such as phenylcarbazole and polyvinylcarbazole, fluorene derivatives, TPD(N,N'-bis(3-methylphenyl)-N, Triphenylamine derivatives such as N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), NPB(N ,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), etc. These are used alone. Or, two or more types may be mixed.
  • the hole transport region 30 may be manufactured through a conventional method known in the art. For example, there are vacuum evaporation method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging method (Laser Induced Thermal Imaging, LITI), and the like, but is not limited thereto.
  • the light emitting layer 40 included in the organic material layer (A) of the present invention is a layer in which holes and electrons meet to form excitons, and the color of light emitted by the organic electroluminescent device according to the material forming the light emitting layer 40 is It can be different.
  • the light emitting layer 40 may include a host and a dopant, and the mixing ratio thereof may be appropriately adjusted within a range known in the art.
  • the host in the range of 70 to 99.9% by weight and the dopant in the range of 0.1 to 30% by weight may be included.
  • the emission layer 40 when the emission layer 40 is blue fluorescence, green fluorescence, or red fluorescence, it may include 80 to 99.9% by weight of a host and 0.1 to 20% by weight of a dopant.
  • the emission layer 40 when the emission layer 40 is blue fluorescence, green fluorescence, or red phosphorescence, it may include 70 to 99% by weight of a host and 1 to 30% by weight of a dopant.
  • the host included in the light emitting layer 40 of the present invention is not particularly limited as long as it is known in the art, and non-limiting examples thereof include an alkali metal complex; Alkaline earth metal complexes; Or condensed aromatic ring derivatives.
  • aluminum complexes aluminum complexes, beryllium complexes, anthracene derivatives, pyrene derivatives, triphenylene derivatives, carbazole derivatives, dibenzofuran derivatives, and dibenzos that can increase the luminous efficiency and lifetime of organic electroluminescent devices. It is preferred to use a thiophene derivative, or a combination of one or more thereof.
  • the dopant included in the light-emitting layer 40 of the present invention is not particularly limited as long as it is known in the art, and non-limiting examples thereof include anthracene derivatives, pyrene derivatives, arylamine derivatives, iridium (Ir) or platinum (Pt ), and the like.
  • the dopant may be classified into a red dopant, a green dopant, and a blue dopant, and red dopants, green dopants and blue dopants commonly known in the art may be used without particular limitation.
  • red dopant examples include PtOEP (Pt(II) octaethylporphine: Pt(II) octaethylporphine), Ir(piq)3 (tris(2-phenylisoquinoline)iridium: tris(2-phenylisoquinoline) ) Iridium), Btp2Ir(acac) (bis(2-(2'-benzothienyl)-pyridinato-N,C3')iridium(acetylacetonate): bis(2-(2'-benzothienyl)-pyridinato-N , C3') iridium (acetylacetonate)), or a mixture of two or more thereof.
  • PtOEP Pt(II) octaethylporphine: Pt(II) octaethylporphine
  • Ir(piq)3 tri
  • non-limiting examples of the green dopant include Ir(ppy)3 (tris(2-phenylpyridine) iridium: tris(2-phenylpyridine) iridium), Ir(ppy)2(acac) (Bis(2-phenylpyridine)( Acetylacetonato)iridium(III): bis(2-phenylpyridine)(acetylaceto) iridium(III)), Ir(mppy)3 (tris(2-(4-tolyl)phenylpiridine)iridium: tris(2-(4- Tolyl)phenylpyridine) iridium), C545T (10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano [6 ,7,8-ij]-quinolizin-11-one: 10-(2-benzothiazolyl)-1,1,7,7-tt
  • non-limiting examples of the blue dopant include F2Irpic (Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III): bis[3,5-difluoro-2-( 2-pyridyl)phenyl(picolinato) iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, DPVBi (4,4'-bis(2,2'-diphenylethen-1-yl) )biphenyl: 4,4'-bis(2,2'-diphenylethen-1-yl)biphenyl), DPAVBi (4,4'-Bis[4-(diphenylamino)styryl]biphenyl: 4,4' -Bis(4-diphenylaminostyryl)biphenyl), TBPe (2,5,8,11-tetra-tert-butyl peryl
  • the light emitting layer 40 includes a red light emitting layer comprising a red phosphorescent material; A green light-emitting layer comprising a green phosphorescent material; Alternatively, it may be a blue light-emitting layer including a blue phosphorescent material or a blue phosphorescent material. Preferably, it may be a light emitting layer including a green phosphorescent material.
  • the above-described light emitting layer 40 may be a single layer or may be formed of a plurality of layers of two or more layers.
  • the organic electroluminescent device may emit light of various colors.
  • the present invention can provide an organic electroluminescent device having a mixed color by providing a plurality of light emitting layers made of different materials in series.
  • the driving voltage of the device increases, while the current value in the organic electroluminescent device is constant, thereby providing an organic electroluminescent device having improved luminous efficiency by the number of emission layers.
  • the electron transport region 50 included in the organic material layer A serves to transfer electrons injected from the cathode 20 to the emission layer 40.
  • the electron transport region 50 may include at least one selected from the group consisting of the electron transport auxiliary layer 53, the electron transport layer 51, and the electron injection layer 52. At this time, in consideration of the characteristics of the organic electroluminescent device, it is preferable to include all of the electron transport auxiliary layer 53, the electron transport layer 51, and the electron injection layer 52 described above.
  • the electron injection layer 52 may use an electron injection material having easy electron injection and high electron mobility without limitation.
  • the electron injection material that can be used include the above bipolar compound, anthracene derivative, heteroaromatic compound, alkali metal complex compound, and the like.
  • the electron transport region 50 may be co-deposited with an n-type dopant to facilitate injection of electrons from the cathode.
  • an alkali metal complex compound known in the art may be used without limitation, and examples thereof include an alkali metal, an alkaline earth metal, or a rare earth metal.
  • the electron transport auxiliary layer 53 may prevent excitons or holes generated in the light emitting layer 40 from diffusing into the electron transport region.
  • the electron transport auxiliary layer 53 serves to prevent holes from diffusing or moving to the electron transport layer 51, thereby improving the life of the organic EL device. That is, holes are blocked by the high energy barrier of the electron transport auxiliary layer 53 and diffuse to the electron transport layer 51 or cannot move and remain in the light emitting layer 40.
  • the electron transport auxiliary layer 53 may be made of a material having conventional electron transport characteristics known in the art without limitation.
  • oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (eg, BCP), heterocyclic derivatives containing nitrogen, and the like may be included.
  • the compound (material) constituting the electron transport auxiliary layer 53 includes a six-membered moiety represented by the following formula (1); A 5-membered moiety represented by the following formula (2); And at least one electron withdrawing (EWG) moiety among polycyclic moieties in which the six-membered moiety and the five-membered moiety are condensed.
  • EWG electron withdrawing
  • X 1 to X 6 and Y 1 to Y 5 are the same as or different from each other, and each independently N or C(R), provided that at least one of the X 1 to X 6 and Y 1 to Y 5 is N,
  • a plurality of Rs are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 to C 60 aryl group, 5 to 60 nuclear atoms Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C aryl phosphine oxide 60 group and a
  • the phosphine group, the arylphosphine oxide group, and the arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • the compound constituting the electron transport auxiliary layer 53 (e.g., an electron transport auxiliary layer material) contains at least one nitrogen-containing heteroaromatic ring containing at least one nitrogen (N), that is, an electron withdrawing group (EWG). As a result, excellent electronic characteristics are exhibited. Accordingly, when a compound having a 6-membered or 5-membered moiety represented by Formulas 1 to 2 or a polycyclic moiety in which they are condensed is applied as a material of the electron transport auxiliary layer 53, electrons are removed from the cathode 20. Since it can be well received, electrons can be smoothly transferred to the light emitting layer 40, thereby lowering the driving voltage of the device 100 and inducing high efficiency and long life.
  • N nitrogen
  • EWG electron withdrawing group
  • the material of the electron transport auxiliary layer 53 not only has a high triplet energy, but also the molecular weight of the compound is significantly increased through the control of various types of substituents introduced into the parent nucleus and the position of introduction, resulting in improved glass transition ionicity and high Can have thermal stability.
  • the organic electroluminescent device 100 including the same can greatly improve durability and lifespan characteristics.
  • the electron withdrawing (EWG) moiety included in the compound constituting the electron transport auxiliary layer 53 may be further specified by any one selected from the following structural formula group. However, it is not particularly limited thereto.
  • the compound constituting the electron transport auxiliary layer 53 (e.g., an electron transport auxiliary layer material) is different from the electron attracting device (EWG), and the electron attracting device (EWG ) It may contain at least one conventional electron donor (EDG) moiety known in the art having higher electron donation.
  • EWG electron withdrawing group
  • EDG electron donor
  • the electron donor (EDG) moiety may be embodied as any one selected from the group of substituents represented by the following structural formula, but is not particularly limited thereto.
  • Z 1 to Z 3 are the same as or different from each other, and each independently selected from the group consisting of NR 3 , O, S, and CR 4 R 5 ,
  • R 1 to R 5 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ an aryl boronic of C 60, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group
  • n are each independently an integer of 0 to 4,
  • a boron group, a phosphine group, a phosphine oxide group, and an arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group , C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group
  • the electron transport region 50 may be manufactured through a conventional method known in the art. For example, there are vacuum evaporation method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging method (Laser Induced Thermal Imaging, LITI), and the like, but is not limited thereto.
  • the organic functional layer 60 included in the organic material layer (A) according to the present invention is an organic layer that is additionally inserted between the light emitting layer 40 and the electron transport auxiliary layer 53.
  • the organic functional layer 60 is an organic layer in which two adjacent organic material layers, that is, the material of the light emitting layer 40 and the material of the electron transport auxiliary layer 53, are mixed with each other to be co-depositioned. Since the organic functional layer 60 uses the same material as the material of the organic layer adjacent to each other, it exhibits a barrier-free effect of lowering the barrier between adjacent organic material layers, and thus the electrons injected from the auxiliary electron transport layer 53 are used. (electron) can be smoothly supplied from the organic layer (A) to the emission layer 40. Accordingly, since the possibility of forming excitons by meeting holes and electrons in the emission layer 40 increases, the luminous efficiency of the organic electroluminescent device can be improved and lifespan characteristics can be significantly improved.
  • organic functional layer 60 In order for the organic functional layer 60 according to the present invention to smoothly exhibit the barrier-free effect described above, adjacent organic material layers, such as the light-emitting layer 40, the electron transport auxiliary layer 53, and the electron transport layer 51 There is a need to adjust the physical properties between materials as follows.
  • the absolute value of the HOMO (highest occupied molecular orbital) energy level of the electron transport auxiliary layer 53 may be higher than the absolute value of the HOMO energy level of the light emitting layer 40 ( See Figure 3 below).
  • the emission layer 40 may refer to a host.
  • the difference between the absolute value of the HOMO energy level of the electron transport auxiliary layer 53 and the absolute value of the HOMO energy level of the light emitting layer 40 may be greater than 0 eV and less than 1.5 eV, and more specifically 0 It may be greater than eV and less than 1.0 eV.
  • the electron transport auxiliary layer 53 forms an energy barrier, so that holes existing in the light emitting layer 40 diffuse to the electron transport auxiliary layer 53 or It does not move and stays in the light emitting layer 40. Accordingly, the possibility of forming excitons by meeting holes and electrons in the emission layer 40 is increased, thereby improving the luminous efficiency of the organic electroluminescent device 100 and significantly improving the lifetime characteristics.
  • the LUMO (lowest unoccupied molecular orbital) energy level of the electron transport auxiliary layer 53 is two adjacent organic material layers, specifically the emission layer 40, the electron transport layer 51 and the emission layer. (40) to exist between.
  • the absolute value of the LUMO energy level of the electron transport auxiliary layer 53 is lower than the absolute value of the LUMO energy level of the electron transport layer 51 and higher than the absolute value of the LUMO energy level of the light emitting layer 40 Can (see Fig. 4 below).
  • a difference between the LUMO energy level of the electron transport auxiliary layer 53 and the LUMO energy level of the electron transport layer 51 may be greater than 0 eV and less than 1.0 eV.
  • the difference between the LUMO energy level value of the electron transport auxiliary layer 53 and the absolute value of the LUMO energy level of the emission layer 40 may be in the range of 0 to 1.0 eV, and more specifically greater than 0 eV, 1.0 It may be less than or equal to eV.
  • the organic functional layer 60 may be manufactured according to a method known in the art by using the material of the light emitting layer 40 and the material of the electron transport auxiliary layer 53.
  • it may be formed by co-depositioning a material of the light emitting layer 40 and a material of the electron transport auxiliary layer 53 at a predetermined ratio.
  • the organic functional layer 60 is not particularly limited as long as it includes the material of the light emitting layer 40 and the material of the electron transport auxiliary layer 53, as long as the components, structure, thickness, etc. of the organic functional layer 60 are included.
  • the organic functional layer 60 is a single layer formed by co-depositing a material of the light-emitting layer 40 and a material of the electron transport auxiliary layer 53, or the material of the light-emitting layer 40 and the auxiliary layer 53 )
  • a mixture of materials; and at least one heterogeneous material may be a mixture of a mono-layer.
  • it may have a multi-layer structure in which two or more different materials are stacked by forming separate layers, respectively.
  • the organic functional layer 60 is an electron transport auxiliary layer 53 material containing at least one or more 6-membered moieties, 5-membered moieties, or condensed polycyclic moieties represented by Formulas 1 to 2, and It includes a host material and a dopant material contained in the emission layer 40.
  • the mixing ratio of the material of the electron transport auxiliary layer 53 and the host material is not particularly limited, for example, 5 to 95: 95 to 5 weight ratio, specifically 5 to 90: 95 to 10 weight ratio I can.
  • the content of the dopant material may be appropriately adjusted within a conventional range known in the art.
  • the dopant may be included in an amount of 0.5 to 30 parts by weight based on the total weight (eg, 100 parts by weight) of the electron transport auxiliary layer 53 material and the host material, but is not particularly limited thereto.
  • the organic light-emitting device 100 of the present invention may further include a light-emitting auxiliary layer (not shown) disposed between the hole transport region 30 and the light-emitting layer 40.
  • a light-emitting auxiliary layer (not shown) disposed between the hole transport region 30 and the light-emitting layer 40.
  • the light-emitting auxiliary layer serves to transport the holes moved from the hole transport region 30 to the light-emitting layer 40 and controls the thickness of the organic material layer (A).
  • This light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer 32, and has a high triplet energy to prevent excitons of the light-emitting layer 40 from diffusing to the hole transport layer 32.
  • This light emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport region. Further, the auxiliary light emitting layers of the red, green, and blue organic light emitting devices may be made of the same material.
  • the material for the light-emitting auxiliary layer is not particularly limited, and examples thereof include carbazole derivatives or arylamine derivatives.
  • Non-limiting examples of the light emission auxiliary layer that can be used include NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'-bis-(3-methylphenyl)-N, N'-bis ( phenyl)-benzidine), s-TAD, MTDATA(4, 4', 4′′-Tris(N-3-methylphenyl-Nphenyl-amino)-triphenylamine). These may be used alone or in combination of two or more.
  • the light emission auxiliary layer may include a p-type dopant in addition to the above-described material. As the p-type dopant, a known p-type dopant used in the art may be used.
  • the organic electroluminescent device 100 of the present invention may further include a capping layer (not shown) disposed on the above-described cathode 20.
  • the capping layer serves to protect the organic light emitting device and help light generated from the organic material layer to be efficiently emitted to the outside.
  • the capping layer is tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6′- (2′,2′′-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4′-bis[N-(1-napthyl)-N-phenyl-amion] biphenyl ( ⁇ -NPD), N,N′-diphenyl-N,N′-bis(3-methylphenyl) -1,1′- It may contain at least one selected from the group consisting of biphenyl-4,4'-diamine (TPD), 1,1'-bis(di-4-tolylaminophenyl) cyclohexane (TAPC).
  • TPD biphenyl-4,4'-diamine
  • TAPC 1,1'-bis(di-4-tolylaminophenyl) cyclohexane
  • the material forming the capping layer is inexpensive compared to
  • Such a capping layer may be a single layer, but may include two or more layers having different refractive indices, so that the refractive index gradually changes while passing through the two or more layers.
  • the capping layer may be manufactured by a conventional method known in the art, and for example, various methods such as a vacuum deposition method, a spin coating method, a cast method, or a Langmuir-Blodgett (LB) method may be used.
  • various methods such as a vacuum deposition method, a spin coating method, a cast method, or a Langmuir-Blodgett (LB) method may be used.
  • the organic light emitting device 100 of the present invention including the above-described configuration may be manufactured according to a conventional method known in the art. For example, after vacuum depositing an anode material on a substrate, an organic light-emitting device may be manufactured by vacuum-depositing a material of a hole transport area material, a light emitting layer material, an electron transport area material, and a cathode material on the anode in order. .
  • FIG. 2 is a diagram illustrating a structure of an organic electroluminescent device according to another embodiment of the present invention.
  • the organic electroluminescent device 200 includes an anode 10; A hole transport region 30; A light emitting layer 40; An electron transport region 50 and a cathode 20 are sequentially stacked, and the electron transport region 50 includes an electron transport auxiliary layer 53, an electron transport layer 51, and an electron injection layer 52. And at least one organic functional layer disposed between the emission layer 40 and the electron transport auxiliary layer 53, and in which materials of the emission layer 40 and the electron transport auxiliary layer 53 are mixed in a predetermined ratio It has a structure containing 60.
  • the hole transport region 30 may include at least one of a hole injection layer 31, a hole transport layer 32, and a hole transport auxiliary layer 33, preferably a hole injection layer 31, a hole transport layer It includes both (32) and the hole transport auxiliary layer (33).
  • the hole transport auxiliary layer 33 is not particularly limited as long as it is a material having a low hole injection barrier and high hole mobility, and a material known in the art may be used without limitation. As an example, it may include a carbazole derivative, a fluorene derivative, a triphenylamine derivative, and the like.
  • the hole transport auxiliary layer 33 is a vacuum deposition method, a spin coating method, a cast method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal method, as known in the art. Imaging, LITI) or the like, but is not limited thereto.
  • each of the components 10, 20, 30-32, 40, and 51-53 of the organic electroluminescent device illustrated in FIG. 2 is the same as that of FIG. 1, and thus individual descriptions thereof will be omitted.
  • the organic electroluminescent devices 100 and 200 according to the present invention have a structure in which an anode 10, an organic material layer (A, A'), and a cathode 20 are sequentially stacked, but the anode 10 and the organic material layer (A, A') or between the cathode 20 and the organic material layers (A, A') may further include an insulating layer or an adhesive layer.
  • the organic electroluminescent device according to the present invention may have excellent lifespan characteristics because, when voltage, current, or both are applied, the life time of initial brightness is increased while maintaining maximum luminous efficiency.
  • the compounds of the present invention were prepared as follows, and their HOMO, LUMO, and triplet energies were measured by methods known in the art, respectively, and are shown in Table 1 below. In addition, ADN compound and Alq 3 compound were used as controls.
  • the bandgap energy of each compound was obtained from the UV spectrum, and then the LUMO energy level was calculated as the difference between the bandgap energy and the HOMO energy level.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power Sonic 405, Hwashin Tech
  • a blue organic electroluminescent device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that the organic functional layer was not used and the emission layer was deposited at 30 nm.
  • the blue organic electric field of Comparative Example 2 was carried out in the same manner as in Example 1, except that an electron transport auxiliary layer (eg, compound 1) and a compound different from the light emitting layer material (eg, compound 5) were used as organic functional layer components.
  • An electron transport auxiliary layer eg, compound 1
  • a compound different from the light emitting layer material eg, compound 5
  • NPB, ADN, and Alq 3 used in Examples 1 to 14 and Comparative Example 1 are as follows, respectively.
  • the blue organic electroluminescent devices of Examples 1 to 14 including organic functional layers in which materials of the light emitting layer and the electron transport auxiliary layer are mixed according to the present invention are compared without the organic functional layer.

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Abstract

La présente invention peut concerner un dispositif électroluminescent organique comprenant une couche fonctionnelle organique qui est disposée entre une couche électroluminescente et une couche auxiliaire de transport d'électrons et dans lequel un matériau de la couche électroluminescente et un matériau de la couche auxiliaire de transport d'électrons sont mélangés et co-déposés, et ainsi le dispositif électroluminescent organique présente simultanément une haute efficacité lumineuse, une faible tension d'attaque, une longue durée de vie, et analogues.
PCT/KR2020/010271 2019-08-06 2020-08-04 Dispositif électroluminescent organique Ceased WO2021025433A1 (fr)

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