WO2021177616A1 - Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant - Google Patents

Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant Download PDF

Info

Publication number
WO2021177616A1
WO2021177616A1 PCT/KR2021/001707 KR2021001707W WO2021177616A1 WO 2021177616 A1 WO2021177616 A1 WO 2021177616A1 KR 2021001707 W KR2021001707 W KR 2021001707W WO 2021177616 A1 WO2021177616 A1 WO 2021177616A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
layer
organic
mmol
Prior art date
Application number
PCT/KR2021/001707
Other languages
English (en)
Korean (ko)
Inventor
최태섭
최지영
윤부용
박형근
김대식
이형동
Original Assignee
덕산네오룩스 주식회사
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 덕산네오룩스 주식회사 filed Critical 덕산네오룩스 주식회사
Publication of WO2021177616A1 publication Critical patent/WO2021177616A1/fr

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/80—Constructional details
    • H10K30/865—Intermediate layers comprising a mixture of materials of the adjoining active 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]
    • H10K50/14—Carrier transporting layers
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to an organic electric device including a light efficiency improving layer and an electronic device including the same.
  • the organic light emitting device is a self-luminous device, and has a wide viewing angle and excellent contrast, as well as a fast response time, excellent luminance, driving voltage and response speed characteristics, and multicolorization is possible.
  • Such an organic light emitting device has a structure in which a first electrode (anode), a hole transport region, a light emitting layer, an electron transport region, and a second electrode (cathode) are sequentially formed on a substrate. Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons, and light is generated as the excitons change from an excited state to a ground state.
  • the luminous efficiency of the organic light emitting diode can be generally divided into internal luminescent efficiency and external liminescent efficiency.
  • the internal luminous efficiency is related to how efficiently excitons are generated and light conversion is performed in the organic layer interposed between the first and second electrodes (that is, between the anode and the cathode), such as a hole transport layer, a light emitting layer, and an electron transport layer, etc.
  • External luminous efficiency refers to the efficiency at which light generated in the organic layer is extracted to the outside of the organic light emitting device, and even if high light conversion efficiency is achieved in the organic layer (that is, , even if the internal luminous efficiency is high), if the external luminous efficiency is low, the overall luminous efficiency of the organic light emitting diode is inevitably reduced.
  • the top device structure has a large optical energy loss due to surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflective film, and emitted toward the cathode.
  • SPP surface plasmon polariton
  • one of the important methods for improving the shape and efficiency of the EL spectrum is a method of applying a capping layer to a top cathode type.
  • metals such as Al, Pt, Ag, and Au are mainly used as cathode electrodes, and SSP is generated on the surface of these metal electrodes.
  • SSP is generated on the surface of these metal electrodes.
  • the cathode is used as Ag
  • the light emitted by the Ag of the cathode is quenched by the SPP (light energy loss due to Ag) and the efficiency is reduced.
  • an object of the present invention is to provide an organic electric device having significantly improved luminous efficiency and color purity by forming a light efficiency improving layer with a specific compound, and an electronic device including the same.
  • the present invention provides an organic electric device comprising a compound represented by the following formula in a light efficiency improving layer and an electronic device thereof.
  • the compound according to the present invention as a material for the light efficiency improvement layer, the luminous efficiency and color purity of the organic electric device can be improved.
  • 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
  • organic electric device 110 first electrode
  • first hole transport layer 340 first light emitting layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto.
  • the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
  • fluorenyl group refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenyl group
  • the fluorenyl group or The fluorenylene group includes a case in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.
  • Substituted fluorenyl group means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, etc. may all be called a fluorene group.
  • the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.
  • heterocyclic group used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.
  • aliphatic ring group used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.
  • the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may.
  • the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'.
  • pyrimidine regardless of the valence, it can be described as 'pyrimidine', or in the case of monovalent, as a pyrimidinyl group, in the case of divalent, as the 'name of the group' of the corresponding valence, such as pyrimidinylene. have.
  • the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described.
  • R 1 when a is an integer of 1, one substituent R 1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same as or different from each other.
  • the number in 'number-condensed ring' indicates the number of rings to be condensed.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
  • a ring when expressed in the form of a 'numeric atom' such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring.
  • thiophene or furan may correspond to a 5-membered ring
  • benzene or pyridine may correspond to a 6-membered ring.
  • the ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60
  • An aliphatic ring group may be selected from the group consisting of.
  • 'neighboring groups' refers to each other when describing the following chemical formula as an example, R 1 and R 2 each other , R 2 and R 3 each other , R 3 and R 4 each other , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and not immediately adjacent, such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included.
  • substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
  • the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
  • 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). and an organic material layer formed between the second electrode 170 and the light efficiency improving layer 180 formed on the first electrode 170 .
  • the first electrode 110 may be an anode (anode)
  • the second electrode 170 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 .
  • the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .
  • the light efficiency improving layer 180 is formed on one side of the second electrode 170 that is not in contact with the organic material layer.
  • the thickness of the light efficiency improving layer may be 30 ⁇ 120nm.
  • the lower limit of the thickness of the light efficiency improving layer may be, for example, 40 nm or more, 50 nm or more, or 55 nm or more.
  • the upper limit of the thickness of the light efficiency improving layer may be, for example, 100 nm or less, 80 nm or less, or 65 nm or less.
  • the light efficiency improving layer may have a refractive index of 1.85 or more for light having a wavelength of 450 to 750 nm.
  • the upper limit of the refractive index of the light efficiency improving layer is not particularly limited, but may be, for example, 3.0 or less or 2.5 or less.
  • the light efficiency improving layer 180 is formed on the second electrode 170 in the top emission method, the light efficiency improving layer is also on one side of both surfaces of the first electrode 110 that is not in contact with the organic material layer. can be formed.
  • a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
  • the organic electric device 200 includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
  • a light emitting auxiliary layer 220 a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
  • an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .
  • the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
  • an organic electric device 300 includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
  • CGL charge generating layer
  • the organic electric device includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and the light efficiency improving layer 180 may be included.
  • the first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 .
  • the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 .
  • the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.
  • a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 .
  • the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 .
  • the charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.
  • the first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but is not limited thereto.
  • n may be an integer of 1 to 5.
  • the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
  • an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
  • the compound represented by Formula 1 of the present invention as a material for the light efficiency improving layer 180, it is possible to significantly improve the luminous efficiency and color purity while improving the lifespan of the organic electric device.
  • the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 and the electron injection layer 160 , a material that can be used as the cathode 170 is deposited on the organic material layer, and then It may be manufactured by forming the light efficiency improving layer 180 on the cathode 170 .
  • a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 and the electron injection layer 160
  • an auxiliary light emitting layer 220 may be formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.
  • the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
  • the organic electric device may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.
  • Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.
  • An organic electric device includes a first electrode; a second electrode; at least one organic material layer formed between the first electrode and the second electrode; and a light efficiency improving layer formed on one surface of both surfaces of the first electrode not in contact with the organic material layer or on one surface of both surfaces of the second electrode not in contact with the organic material layer, wherein the light efficiency improving layer is represented by the following formula (1) compounds.
  • X and Z independently of one another are O or S, and Y is N(R), C(R')(R"), O or S.
  • Ar 1 To Ar 4 are each independently a C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; -L'-N(R a )(R b ); and Formula 1-1, and at least one of Ar 1 to Ar 4 is represented by Formula 1-1.
  • L 1 To L 7 are each independently a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; C 6 ⁇ C 30 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
  • n and p are each an integer of 0-4, m is an integer of 0-2, and when each of these is an integer of 2 or more, each of R 1 , each of R 2 , and each of R 3 are the same as or different from each other.
  • o is an integer of 0 to 2, and when o is 2, each of L 1 , each of L 2 , each of L 3 , each of Ar 1 , and each of Ar 2 are the same as or different from each other.
  • the L' is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the R, R a and R b are each independently a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • R' and R" are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, at least one heteroatom of S, Si and P Containing C 2 ⁇ C 60 Heterocyclic group; C 3 ⁇ C 60 Aliphatic ring group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; And C 6 ⁇ C 30 It is selected from the group consisting of an aryloxy group, R' and R" may be bonded to each other to form a ring. When R' and R" combine with each other to form a ring, a spiro compound may be formed.
  • the aryl group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , may be an aryl group such as C 18 , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, and the like.
  • the arylene group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 to C 20 , C 6 to C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 may be an arylene group, Specifically, it may be phenylene, biphenyl, naphthylene, terphenyl, and the like.
  • the heterocyclic group is, for example, C 2 ⁇ C 30 , C 2 ⁇ C 24 , C 2 ⁇ C 20 , C 2 ⁇ C 18 , C 2 ⁇ C 16 , C 2 ⁇ C 12 , C 2 ⁇ C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , may be a heterocyclic group such as C 18 , and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, Indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole
  • the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkyl group such as C 4 , specifically methyl, ethyl, propyl, t-butyl, and the like.
  • the aryl group is, for example, C 6 -C 20 , C 6 -C 18 , C 6 -C 16 , C 6 -C 14 , C 6 -C 12 , C 6 -C 10 , C It may be an aryl group such as 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 .
  • the heterocyclic group is, for example, C 2 ⁇ C 20 , C 2 ⁇ C 18 , C 2 ⁇ C 16 , C 2 ⁇ C 12 , C 2 ⁇ C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , C 18 may be a heterocyclic group.
  • the alkyl group may be, for example, an alkyl group such as C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , C 4 .
  • Formula 1 may be represented by Formula 2 or Formula 3 below.
  • Formula 1 may be represented by one of Formulas 4 to 7 below.
  • the Chemical Formula 1-1 may be represented by the following Chemical Formula 1-1A.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the compound represented by Formula 1 according to the present invention (final product) may be prepared by reacting Core 1 and Sub1 as shown in Scheme 1 below, but is not limited thereto.
  • Hal 1 and Hal 2 are each I, Br or Cl, L′ is L 2 or L 5 , L′′ is L 3 or L 6 , Ar′ is Ar 1 or Ar 3 , Ar′′ is Ar 2 or Ar 4 Lim)
  • Core 1 of Scheme 1 may be synthesized by the reaction routes of Schemes 2 to 5, but is not limited thereto.
  • Hal 3 is halogen.
  • the compound belonging to Core1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • Sub1 of Scheme 1 may be synthesized by the reaction route of Scheme 6 below, but is not limited thereto.
  • the compound belonging to Sub1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • Core1-1 (20 g, 50.65 mmol) to Sub1-1 (20.43 g, 50.65 mmol), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82) mmol), NaO t -Bu (7.87 g, 81.87 mmol), and toluene (169 ml) were added and stirred at 130°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.90 g (yield: 86%) of the product.
  • N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate -diamine (hereinafter abbreviated as '2-TNATA') film was vacuum deposited to form a 60 nm thick hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as 'NPB') film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • 9,10-di(naphthalen-2-yl)anthracene as a host and BD-052X (Idemitsu kosan) as a dopant were used on the hole transport layer, but doped with dopants so that these weight ratios were 93:7 A light emitting layer was formed.
  • 'BAlq' (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • Alq 3 tris(8-quinolinol)aluminum
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode
  • the compound P-1 of the present invention was A film was formed to a thickness of 60 nm to form a light efficiency improving layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light efficiency improving layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • Ir(ppy) 3 tris(2-phenylpyridine)-iridium
  • An organic electroluminescent device was manufactured in the same manner as in Example 17, except that the light efficiency improving layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 17, except that Comparative Compound A was used as a material for the light efficiency improving layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the light efficiency improving layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 33, except that Comparative Compound A was used as a material for the light efficiency improving layer.
  • SPPs Surface plasmon polaritons
  • TE transverse electric
  • TM transverse magnetic
  • the compound of the present invention has a tetracyclic core in which oxazole and thiazole moieties having a high refractive index in the visible wavelength band (range of 430 nm to 780 nm) are fused, and at least one amino group is bonded to this core, It has a structure in which a substituent such as benzoxazole and benzothiazole, which can increase the refractive index, is also bonded to the amino group.
  • the compound of the present invention has a higher refractive index than the comparative compound A due to synergy due to the combination of the core and the substituent, and as a result, the light generated in the organic layer is extracted to the outside of the organic light emitting device by the principle of constructive interference. As this increases, the overall light efficiency of the organic light emitting diode is improved.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électronique organique comprenant une couche de recouvrement et un appareil électronique le comprenant, et la couche de recouvrement est formée avec un composé représenté par la formule chimique 1, selon la présente invention, et ainsi l'efficacité et la pureté de couleur d'un dispositif électronique organique peuvent être améliorées.
PCT/KR2021/001707 2020-03-04 2021-02-09 Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant WO2021177616A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2020-0026915 2020-03-04
KR1020200026915A KR20210111971A (ko) 2020-03-04 2020-03-04 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치

Publications (1)

Publication Number Publication Date
WO2021177616A1 true WO2021177616A1 (fr) 2021-09-10

Family

ID=77612921

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/001707 WO2021177616A1 (fr) 2020-03-04 2021-02-09 Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant

Country Status (2)

Country Link
KR (1) KR20210111971A (fr)
WO (1) WO2021177616A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114436971A (zh) * 2022-02-25 2022-05-06 陕西维世诺新材料有限公司 二(4-(苯并杂唑-2-基)苯基)甲胺衍生物及制备方法
CN114874235A (zh) * 2022-05-23 2022-08-09 武汉天马微电子有限公司 一种杂环化合物及其应用
CN114989181A (zh) * 2022-06-30 2022-09-02 武汉天马微电子有限公司 一种杂环芳胺化合物、有机电致发光器件和显示面板
WO2023241136A1 (fr) * 2022-06-13 2023-12-21 陕西莱特光电材料股份有限公司 Composé hétérocyclique, appareil électroluminescent organique et dispositif électronique

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113527235A (zh) * 2020-04-16 2021-10-22 东进世美肯株式会社 新型覆盖层用化合物以及包含上述覆盖层用化合物的有机发光元件
CN116323621A (zh) * 2020-12-14 2023-06-23 株式会社Lg化学 新的化合物和包含其的有机发光器件
KR102576738B1 (ko) * 2020-12-17 2023-09-08 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2023177217A1 (fr) * 2022-03-18 2023-09-21 에스에프씨 주식회사 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant
KR102577530B1 (ko) * 2022-11-17 2023-09-12 덕산네오룩스 주식회사 금속패터닝층을 포함하는 유기전기소자 및 그 전자장치

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014003336A1 (fr) * 2012-06-27 2014-01-03 덕산하이메탈(주) Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé
KR20170116927A (ko) * 2016-04-12 2017-10-20 주식회사 엘지화학 유기화합물을 포함하는 캡핑층 및 이를 포함한 유기전계발광소자
CN109824659A (zh) * 2019-03-12 2019-05-31 江苏三月光电科技有限公司 一种基于杂芳基胺类结构的有机化合物及其应用
KR102059550B1 (ko) * 2018-12-12 2019-12-26 (주)랩토 트리벤즈아졸 아민 유도체 및 이를 포함한 유기 전계 발광 소자
KR102080737B1 (ko) * 2019-05-29 2020-02-24 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014003336A1 (fr) * 2012-06-27 2014-01-03 덕산하이메탈(주) Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé
KR20170116927A (ko) * 2016-04-12 2017-10-20 주식회사 엘지화학 유기화합물을 포함하는 캡핑층 및 이를 포함한 유기전계발광소자
KR102059550B1 (ko) * 2018-12-12 2019-12-26 (주)랩토 트리벤즈아졸 아민 유도체 및 이를 포함한 유기 전계 발광 소자
CN109824659A (zh) * 2019-03-12 2019-05-31 江苏三月光电科技有限公司 一种基于杂芳基胺类结构的有机化合物及其应用
KR102080737B1 (ko) * 2019-05-29 2020-02-24 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114436971A (zh) * 2022-02-25 2022-05-06 陕西维世诺新材料有限公司 二(4-(苯并杂唑-2-基)苯基)甲胺衍生物及制备方法
CN114874235A (zh) * 2022-05-23 2022-08-09 武汉天马微电子有限公司 一种杂环化合物及其应用
WO2023241136A1 (fr) * 2022-06-13 2023-12-21 陕西莱特光电材料股份有限公司 Composé hétérocyclique, appareil électroluminescent organique et dispositif électronique
CN114989181A (zh) * 2022-06-30 2022-09-02 武汉天马微电子有限公司 一种杂环芳胺化合物、有机电致发光器件和显示面板

Also Published As

Publication number Publication date
KR20210111971A (ko) 2021-09-14

Similar Documents

Publication Publication Date Title
WO2020226298A1 (fr) Élément électronique organique comprenant un composé pour élément électronique organique, et dispositif électronique associé
WO2021177616A1 (fr) Dispositif électronique organique comprenant une couche de recouvrement et appareil électronique le comprenant
WO2021141356A1 (fr) Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci, et dispositif électronique associé
WO2021206305A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2018016786A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2020226300A1 (fr) Dispositif électrique organique comprenant un composé pour dispositif électrique organique, et dispositif électronique associé
WO2014178532A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2020149711A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
WO2015056965A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2020149710A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2020138726A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2016013816A1 (fr) Élément électrique organique faisant appel à un composé pour élément électrique organique, et dispositif électronique associé
WO2017052099A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2019093666A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique
WO2015080404A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2021029598A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé
WO2016153198A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2021045444A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2019031833A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et dispositif électronique
WO2016013817A2 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2019022435A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2021033970A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2020209514A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément luminescent organique
WO2018225991A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2017014460A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé

Legal Events

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

Ref document number: 21763728

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: 21763728

Country of ref document: EP

Kind code of ref document: A1