[go: up one dir, main page]

WO2019066250A1 - Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci Download PDF

Info

Publication number
WO2019066250A1
WO2019066250A1 PCT/KR2018/009503 KR2018009503W WO2019066250A1 WO 2019066250 A1 WO2019066250 A1 WO 2019066250A1 KR 2018009503 W KR2018009503 W KR 2018009503W WO 2019066250 A1 WO2019066250 A1 WO 2019066250A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
ring
aryl
carbon atoms
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2018/009503
Other languages
English (en)
Korean (ko)
Inventor
채미영
조혜민
조민지
문성윤
이선희
이남걸
이형동
오대환
이가은
박상용
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DukSan Neolux Co Ltd
Original Assignee
DukSan Neolux Co 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
Priority claimed from KR1020180039162A external-priority patent/KR20190038254A/ko
Application filed by DukSan Neolux Co Ltd filed Critical DukSan Neolux Co Ltd
Priority to CN201880063772.6A priority Critical patent/CN111164079B/zh
Priority to CN202310194478.1A priority patent/CN116120192A/zh
Priority to US16/652,383 priority patent/US11450808B2/en
Publication of WO2019066250A1 publication Critical patent/WO2019066250A1/fr
Anticipated expiration legal-status Critical
Priority to US17/346,936 priority patent/US20220278285A1/en
Priority to US18/946,259 priority patent/US20250089557A1/en
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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 a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • a material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.
  • the light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.
  • a host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer.
  • the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency.
  • the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.
  • the efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T 1 value and the intrinsic properties (mobility, interfacial characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time .
  • a light emission auxiliary layer (multilayer hole transport layer) must exist between the hole transport layer and the light emitting layer, It is necessary to develop a light-emitting auxiliary layer.
  • electrons are transferred from the electron transport layer to the light emitting layer and holes are transferred from the hole transport layer to the light emitting layer to recombine electrons and holes in the light emitting layer to form excitons.
  • the material used for the hole transport layer has a low HOMO value and therefore has a low T 1 value.
  • the exciton generated in the light emitting layer is transferred to the hole transport layer, resulting in a charge unbalance in the light emitting layer. And emits light at the interface of the hole transporting layer.
  • the material should have a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, and have a high T1 value and a hole mobility of within a suitable driving voltage range it is urgently required to develop a light-emitting auxiliary layer material having hole mobility.
  • a material forming the organic material layer in the device for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, And it is particularly desired to develop materials for a light emitting host material, a hole transporting layer and a light emitting auxiliary layer.
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity, stability and lifetime of the device, and an organic electronic device using the same and an electronic device thereof.
  • the present invention provides a compound represented by the following general formula (1).
  • the present invention provides a compound represented by the following formula (A).
  • the present invention provides an organic electronic device using the compound represented by Formula 1 or Formula A and an electronic device thereof.
  • the compound according to an embodiment of the present invention not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity, stability and lifetime of the device can be greatly improved.
  • FIG. 1 is an illustration of an organic electroluminescent device according to the present invention.
  • aryl group and arylene group each have 6 to 60 carbon atoms, but are not limited thereto.
  • the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.
  • heterocyclic group as used herein includes not only aromatic rings such as “ heteroaryl group” or “ heteroarylene group”, but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto.
  • heteroatom as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.
  • heterocyclic group used in the present invention means a ring containing a hetero atom such as N, O, S, P or Si instead of carbon forming a ring, and the term “heteroaryl group” or “heteroarylene group” As well as non-aromatic rings, and compounds containing hetero atoms such as SO 2 , P ⁇ O, etc., such as the following compounds, instead of ring-forming carbon, may also be included.
  • fluorenyl group " or " fluorenylene group " used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or” substituted fluorenylene group "means that at least one of the substituents R, R 'and R” is a substituent other than hydrogen, and R and R' Together with a spy compound.
  • spiro compound used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom.
  • atoms shared in two rings are called 'spyro atoms', and they are referred to as 'monospyros,' 'di spyroses,' and 'tri-spyros', depending on the number of spyro atoms contained in a compound.
  • 'Compounds atoms shared in two rings.
  • the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may.
  • a monovalent 'group' may be named 'phenanthryl'
  • a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound.
  • pyrimidine it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine di have.
  • substituent R 1 When a is an integer of 0, substituent R 1 is absent. When a is an integer of 1, one substituent R 1 is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 And R 1 may be the same or different from each other. When a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner. On the other hand, the indication of hydrogen bound to the carbon which forms the benzene ring may be omitted.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • an organic electroluminescent device 100 includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110, And an organic layer between the second electrode 180 and the compound according to the present invention.
  • the first electrode 120 may be an anode and the second electrode 180 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 injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, an electron injecting layer 170, and the like sequentially stacked on the first electrode 120 . At this time, at least one of these layers may be omitted or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, a buffer layer 141, It may serve as a hole blocking layer.
  • the organic electronic device may further include a protective layer or a light efficiency improvement layer.
  • the light-efficiency-improvement layer may be formed on a surface of the first electrode that is not in contact with the organic layer or a surface of the second electrode that is not in contact with the organic layer.
  • the compound according to one embodiment of the present invention applied to the organic layer includes a hole injecting layer 130, a hole transporting layer 140, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, an electron transporting layer 160, 170, a host or dopant of the light-emitting layer 150, or a material of the light-efficiency-improvement layer.
  • the compound according to Formula 1 of the present invention can be used as a material for the light-emitting layer 150, preferably as a host material for the light-emitting layer.
  • the compound according to Formula 1 of the present invention and the compound according to Formula 12 The mixture may be used as a host material, and the compound according to Formula 20 of the present invention can be used as a material of the hole transporting layer or the light emitting auxiliary layer.
  • the compound represented by the formula (21) or (22) of the present invention is a hole transport layer material, and the compound represented by the formula (23) or (24) can be used as a light emitting auxiliary layer material.
  • the compound represented by the formula (A) can be used as a luminescent auxiliary layer, particularly a green luminescent auxiliary layer material.
  • the band gap, the electrical characteristics, the interface characteristics, and the like may be different depending on which substituent is bonded at any position even though it is the same similar core, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and the T 1 value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.
  • the compound represented by the formula (1) alone or in combination with the compound represented by the formula (1) and the compound represented by the formula (12) is used as the host material in the light emitting layer, or these compounds are used as the light emitting layer material
  • the compound according to Chemical Formula 20 as a material for the hole transport layer or the light emitting auxiliary layer, it is possible to optimize the energy level and T 1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) Efficiency can be improved at the same time.
  • An organic electroluminescent device may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting layer 160.
  • the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. 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 forming method.
  • the organic electroluminescent device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the organic electroluminescent device may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.
  • Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device.
  • the electronic device may be a current or future wired or 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 controller, a navigation device, a game machine, various TVs, and various computers.
  • a compound according to one aspect of the present invention is represented by the following formula (1).
  • each symbol may be defined as follows.
  • X 1 and X 2 are independently of each other S or O, provided that X 1 and X 2 are different from each other. That is, one of X 1 and X 2 is O and the other is S.
  • Ar 1 to Ar 3 independently represent a C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ).
  • Ar 1 to Ar 3 are aryl groups, it is preferably a C 6 to C 30 aryl group or a C 6 to C 20 aryl group, more preferably a C 6 to C 18 aryl group, Phenyl, naphthyl, phenanthrene, terphenyl, and the like.
  • Ar 1 to Ar 3 are a heterocyclic group, preferably a C 2 to C 30 heterocyclic group or a C 2 to C 20 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothiazole, thiophene, thiophene, pyridine, pyrimidoindole, Benzopyrimidine, phenothiazine, phenylphenothiazine, and the like.
  • Ar 1 to Ar 3 are fluorenyl groups, they may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene and the like.
  • Ar 2 and Ar 3 are aryl groups, they may preferably be C 6 to C 30 aryl groups, more preferably C 6 to C 22 aryl groups, still more preferably C 6 to C 18 aryl groups, Illustratively, it may be phenyl, biphenyl, naphthyl, phenanthrene, terphenyl, and the like.
  • Ar 1 to Ar 3 are a heterocyclic group, preferably a C 2 to C 30 heterocyclic group or a C 2 to C 20 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothiazole, thiophene, thiophene, pyridine, pyrimidoindole, Benzopyrimidine, phenothiazine, phenylphenothiazine, and the like.
  • Ar 1 to Ar 3 are fluorenyl groups, they may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene and the like.
  • R 1 to R 4 independently of one another are hydrogen; heavy hydrogen; halogen; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; (R a ) (R b ); and the neighboring groups may be connected to each other to form a C 6 to C 60 aromatic ring, O, N, S, Si, and P Form a fused ring of a C 2 -C 60 heterocycle, a C 3 -
  • Each of a to d is an integer of 0 to 3, and when each of these is an integer of 2 or more, each R 1 , each R 2 , each R 3, or each R 4 is the same or different from each other.
  • R 1 to R 4 are aryl groups, it is preferably a C 6 to C 30 aryl group or a C 6 to C 20 aryl group, more preferably a C 6 to C 18 aryl group, Phenyl, naphthyl, terphenyl, and the like.
  • R 1 to R 4 are a heterocyclic group, preferably a C 2 to C 30 heterocyclic group or a C 2 to C 20 heterocyclic group, more preferably a C 2 to C 8 heterocyclic group, Pyridine, pyridine, quinazoline, and the like.
  • the formed ring is preferably a C 6 to C 20 aromatic ring, or an O, More preferably a C 6 to C 10 aromatic ring, or at least one of O, N, S, Si and P, which is a C 2 to C 20 hetero ring containing at least one hetero atom selected from N, S, Si and P, It may be one of the hetero atoms of the heterocyclic C 2 ⁇ C 10 containing, and the like such as benzene ring, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine.
  • an aromatic ring or a heterocycle containing a benzene ring may be formed together with a benzene ring to which they are bonded, preferably C 6 ⁇ C has 14 aromatic ring or C 2 ⁇ C 14 of the heterocycle can be formed.
  • L ' is a single bond;
  • L ' is an arylene group, preferably an arylene group having 6 to 30 carbon atoms or an arylene group having 6 to 20 carbon atoms, more preferably an arylene group having 6 to 18 carbon atoms, such as phenylene, biphenyl, naphthalene , Terphenyl, and the like.
  • R a and R b are independently of each other hydrogen; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; is selected from the group consisting of.
  • R a and R b are aryl groups, it is preferably a C 6 to C 30 aryl group or a C 6 to C 20 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, biphenyl, Naphthalene, terphenyl, and the like.
  • Ar 1 to Ar 3 , R 1 to R 4 , L ', R a , R b , and R 1 to R 4 are connected to each other to form a ring; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A C 6 -C 20 aryl group
  • Ar 1 to Ar 3 , R 1 to R 4 , A ring formed by connecting neighboring groups of L ', R a , R b and R 1 to R 4 is an aryl group, an arylene group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a heterocyclic group, ,
  • An alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, etc., may be further substituted with at least one substituent selected from the group consisting of a substituent such as deuterium, halogen and the like have.
  • Ar 1 to Ar 3 , R 1 to R 4 When a ring formed by connecting neighboring groups of L ', R a , R b and R 1 to R 4 is further substituted with an aryl group, preferably a C 6 -C 20 aryl group, more preferably C 6 may be further substituted with an aryl group -C 18, such as phenyl, naphthyl, biphenyl, terphenyl and the like.
  • Ar 1 to Ar 3 , R 1 to R 4 When a ring formed by connecting neighboring groups of L ', R a , R b and R 1 to R 4 to each other is further substituted with an alkyl group, preferably a C 1 -C 10 alkyl group, more preferably C 1 alkyl group -C 4, for example, may be further substituted with methyl, t- butyl.
  • an alkyl group preferably a C 1 -C 10 alkyl group, more preferably C 1 alkyl group -C 4, for example, may be further substituted with methyl, t- butyl.
  • the above Ar 1 to Ar 3 , R 1 to R 4 , The ring formed by connecting neighboring groups of L ', R a , R b and R 1 to R 4 may be further substituted with a substituent such as F, CN, ethene or the like.
  • the formula (1) may be represented by one of the following formulas (2) to (11).
  • each symbol is the same as defined in Chemical Formula (1).
  • X 1 , X 2 , Ar 1 to Ar 3 , R 1 to R 4 , a, b, c, d and the like are as defined in formula (1).
  • At least one of Ar 1 to Ar 3 is a substituted or unsubstituted C 6 to C 24 aryl group, more preferably Ar 1 to Ar 3 are all substituted or not substituted A substituted or unsubstituted C 6 to C 12 aryl group, and Ar 2 and Ar 3 may be different from each other.
  • the compound represented by Formula 1 may be the following compound, but is not limited thereto.
  • an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, ≪ / RTI >
  • the organic layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer.
  • a hole injecting layer a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer.
  • one or two or more compounds represented by the above formula (1) can be used as the host material of the light emitting layer.
  • the light emitting layer may further include a compound represented by the following general formula (12).
  • Z 1 to Z 4 , Z 13 to Z 16 independently of one another are C (R) or N and Z 5 to Z 12 independently of one another are C, C (R) or N.
  • L 2 is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of.
  • L 2 is an arylene group
  • it is preferably an arylene group having 6 to 30 carbon atoms or an arylene group having 6 to 20 carbon atoms, more preferably an arylene group having 6 to 18 carbon atoms such as phenyl, naphthyl, biphenyl , Terphenyl, and the like.
  • L 2 is a heterocyclic group
  • it is preferably a C 2 to C 30 heterocyclic group or a C 2 to C 20 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group such as carbazole, Phenylcarbazole, and the like.
  • W is N (Ar 5), N, O, S, C (R ') (R ") or C (R'), and, when combined with L 2 and W is N or C (R ').
  • Ar 4 and Ar 5 are each independently a C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic ring; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; -L ' -N (R ' a ) (R ' b ); And combinations thereof.
  • the term “combination thereof” means, for example, a combination of an aryl group and a heterocyclic group, a combination of an aryl group and an aliphatic ring, and a combination of a heterocyclic group and an aliphatic ring group.
  • R, R 'and R " are each independently of the other hydrogen, deuterium, halogen, C 6 to C 60 aryl, fluorenyl, O, N, S, group 2 or heterocyclic C 60; C 3 ⁇ C aliphatic ring group of 60; an alkyl group of C 1 ⁇ C 50;; C 3 ⁇ C 60 alicyclic and C 6 ⁇ C 60 aromatic ring fused ring group of a C of 2 ⁇ C 20 alkenyl; C 2 ⁇ C 20 alkynyl of; C 1 ⁇ alkoxy group of C 30; C 6 ⁇ C 30 aryloxy; and -L'-N (R a) ( R b) ; Adjacent Rs may be connected to each other to form a ring, or R 'and R " may be connected to each other to form a ring.
  • a ring formed by connecting adjacent Rs to each other or formed by connecting R 'and R " to each other may be a ring formed of a C 6 to C 60 aromatic ring, at least one of O, N, S, Si and P, may be included C 2 ⁇ C 60 heterocyclic, C 3 ⁇ aliphatic ring of C 60, or C 3 ⁇ fused ring of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60 to, and preferably C 6 A C 2 to C 20 aromatic ring, or a C 2 to C 20 hetero ring, more preferably a C 6 to C 10 aromatic ring containing at least one hetero atom selected from O, N, S, Si and P, or O ,
  • a C 2 to C 10 heterocyclic ring containing at least one hetero atom selected from N, S, Si and P and may be, for example, benzene ring, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and
  • L ', R a and R b are as defined in the above formula (1).
  • the formula (12) may be represented by one of the following formulas (13) to (17).
  • At least one of Ar 4 and Ar 5 is a substituted or unsubstituted C 6 to C 30 aryl group, more preferably all of C 6 to C 30 Lt; / RTI >
  • the formula (12) may be represented by the following formula (18) or (19).
  • Ar 4 , Z 1 to Z 16 , and L 2 are the same as defined in Formula 12 above.
  • L 1 is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of.
  • L 1 is an arylene group, preferably an arylene group having 6 to 30 carbon atoms or an arylene group having 6 to 20 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms, such as phenyl, naphthalene, biphenyl And so on.
  • Y is O, S or N-Ar 6 .
  • R a and R b are independently from each other deuterium; halogen; A C 6 -C 20 aryl group; A C 6 -C 20 aryl group substituted by deuterium; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; An arylalkyl group of C 7 -C 20 ; Aryl alkenyl group of C 8 -C 20; is selected from the group consisting of, in combination with each other adjacent to each other a group C 6 ⁇ C 60 aromatic ring, C 2 ⁇ C 60 heterocyclic, C 3 ⁇ C 60 of aliphatic cyclic , or it may form a fused ring of an aromatic ring of C 3 ⁇ C 60 of
  • y is an integer of 0 to 3
  • z is an integer of 0 to 4
  • each of y and z is an integer of 2 or more, each R a or each R b is the same or different from each other.
  • Ar 6 is a C 6 to C 60 aryl group; A C 6 -C 60 aryl group substituted with deuterium; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 cycloalkyl group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; An arylalkyl group of C 7 -C 20 ; And aryl alkenyl group of C 8 -C 20; may be selected from the group consisting of.
  • a r6 is an aryl group of C 6 -C 20; A C 6 -C 20 aryl group substituted by deuterium; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; An arylalkyl group of C 7 -C 20 ; And aryl alkenyl group of C 8 -C 20; may be selected from the group consisting of.
  • the compound represented by Formula 12 may be one of the following compounds, but is not limited thereto.
  • the organic layer of the organic electroluminescent device includes a light emitting layer, a hole transporting layer formed between the first electrode and the light emitting layer, and a light emitting auxiliary layer formed between the light emitting layer and the hole transporting layer, (1), wherein the hole transport layer or the light-emission-assisting layer comprises a compound represented by the following general formula (20).
  • Ar 4 and Ar 5 are each independently a C 6 -C 60 aryl group; A fluorenyl group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; A fused ring group of a C 3 -C 60 aliphatic ring group and a C 6 -C 60 aromatic ring; A C 1 -C 50 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 1 -C 30 alkoxyl group; A C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); Ar 4 and Ar 5 may combine with each other to form a ring.
  • Ar 6 is a C 6 -C 60 aryl group; A fluorenyl group; And a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, or a group selected from the group consisting of the following formulas 1-a to 1-c: Can be selected.
  • Ar 9 to Ar 11 independently represent a C 6 -C 60 aryl group; A fluorenyl group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; A fused ring group of a C 3 -C 60 aliphatic ring group and a C 6 -C 60 aromatic ring; A C 1 -C 50 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 1 -C 30 alkoxyl group; A C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b );
  • L 5 is a C 6 -C 60 arylene group; A fluorenylene group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; And fused ring group of C 3 -C 60 aromatic ring of an aliphatic ring group of C 6 -C 60; may be selected from the group consisting of.
  • L 6 is a single bond; C 6 -C 60 arylene groups; A fluorenylene group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; And fused ring group of C 3 -C 60 aromatic ring of an aliphatic ring group of C 6 -C 60; may be selected from the group consisting of.
  • R 6 to R 9 independently from each other are hydrogen; heavy hydrogen; halogen; An aryl group of C 6 -C 60 ; A fluorenyl group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; A fused ring group of a C 3 -C 60 aliphatic ring group and a C 6 -C 60 aromatic ring; A C 1 -C 50 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 1 -C 30 alkoxyl group; An aryloxy group of C 6 - 30 ; And -L'-N (R a ) (R b );
  • i, and g is an integer of 0 to 4 integer
  • each, j is an integer from 0 to 3, and they each case 2 or more integer
  • a plurality of R 6, a plurality of R 7, a plurality of R 8, a plurality of R 9 Are the same or different.
  • adjacent R 6 , adjacent R 7 , adjacent R 8, or adjacent R 9 may combine with each other to form a ring.
  • the adjacent groups may be bonded to each other to form a C 6 to C 60 aromatic ring, a C 2 to C 60 hetero ring, a C 3 to C 60 aliphatic ring, or a C 3 to C 60 aliphatic ring and a C 6 to C Lt ;
  • RTI ID 0.0 > 60 < / RTI > aromatic rings.
  • L ', R a and R b are as defined in formula (1).
  • Ar 4 to Ar 6 , Ar 9 to Ar 11 , R 6 to R 9 , L < 5 >, L < 6 >, and the rings formed by bonding adjacent groups to each other are each a deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A
  • the light emitting layer may further include a compound represented by the general formula (12).
  • the hole transport layer comprises a compound represented by the following Chemical Formula 21 or 22, and the light emission-assisting layer may include a compound represented by Chemical Formula 23 or Chemical Formula 24 below.
  • Ar 4 is An aryl group of C 6 -C 60 ; A fluorenyl group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a C 3 -C 60 aliphatic cyclic group.
  • At least one of Ar 4 , Ar 5 , Ar 10 and Ar 11 may be represented by the following Formula 24-1.
  • R a ' , R b ' and R c ' are independently of each other hydrogen; heavy hydrogen; halogen; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; And C 3 ⁇ fused ring group of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of, and may be formed adjacent to each other a ring group bonded to each other.
  • the ring may be a C 6 to C 60 aromatic ring, a C 2 to C 60 hetero ring, A C 3 to C 60 aliphatic ring, or a fused ring of a C 3 to C 60 aliphatic ring and a C 6 to C 60 aromatic ring.
  • the plurality of R a ' , the plurality of R b' and the plurality of R c ' may be the same or different from each other when each of l', m 'and n' is an integer of 0 to 4 .
  • Ar 1 ' is a C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of.
  • the rings formed by combining R a ' , R b' , R c ' , and Ar 1' and neighboring groups are deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A C 6 -C 20 aryl group substituted by deuterium;
  • Ar 1 ' and L 5 may independently be a C 6 to C 60 arylene group, and examples thereof include phenyl, biphenyl, o-terphenyl, m-terphenyl, 0.0 > naphthalene. ≪ / RTI >
  • the formula (24) may be represented by the following formula (A).
  • R a ', R b ', R c ', Ar 1', l ', m' and n ' have the same meanings as defined in formula 24-1
  • Ar 2' is Ar 11 of the formula 24 identical and, Ar 3 and Ar 5 in the formula is the same, is the same, and Ar 4 and Ar 4 of formula 24 'and 24 and, a' is an integer from 1 to 3.
  • each symbol in the above formula (A) can be defined as follows.
  • R a ' , R b ' and R c ' are independently of each other hydrogen; heavy hydrogen; halogen; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; And C 3 ⁇ fused ring group of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of, and may be formed adjacent to each other a ring group bonded to each other.
  • the ring may be a C 6 to C 60 aromatic ring, a C 2 to C 60 hetero ring, A C 3 to C 60 aliphatic ring, or a fused ring of a C 3 to C 60 aliphatic ring and a C 6 to C 60 aromatic ring.
  • m 'and n' are each an integer of 0 to 4, and when each of these is an integer of 2 or more, a plurality of R a 's may be the same or different, and a plurality of R b' s may be the same or different from each other And a plurality of R c 's may be the same or different from each other.
  • Ar 1 ' represents a C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of.
  • Ar 1 ' is an arylene group, it may preferably be a C 6 -C 18 aryl group, more preferably a C 6 -C 12 aryl group, such as phenyl, biphenyl, terphenyl, naphthyl and the like .
  • Ar 2 ' , Ar 3' and Ar 4 ' are C 6 -C 60 aryl groups; A fluorenyl group; A C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 -C 60 aliphatic cyclic group; A fused ring group of a C 3 -C 60 aliphatic ring group and a C 6 -C 60 aromatic ring; A C 1 -C 50 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 1 -C 30 alkoxyl group; A C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); Ar 4 and Ar 5 may combine with each other to form a ring.
  • Ar 2 ' is an aryl group, it is preferably a C 6 -C 30 aryl group, more preferably a C 6 -C 18 aryl group such as phenyl, naphthyl, biphenyl, terphenyl and the like.
  • Ar 2 ' is a heterocyclic group, it may preferably be a C 2 -C 30 heterocyclic group, more preferably a C 2 -C 16 heterocyclic group such as dibenzofuran, benzonaphthofuran, etc. .
  • Ar 2 ' is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spiroid fluorene and the like.
  • Ar 3 ' and Ar 4' are aryl groups, it is preferably a C 6 -C 30 aryl group, more preferably a C 6 -C 18 aryl group such as phenyl, biphenyl, terphenyl, naphthyl, tri Phenylene, phenanthrene, and the like.
  • Ar 3 ' and Ar 4' are heterocyclic groups, it is preferably a C 2 -C 30 heterocyclic group, more preferably a C 2 -C 12 heterocyclic group such as dibenzofuran, dibenzothiophene or the like .
  • Ar 3 ' and Ar 4' are fluorenyl groups, 9,9-dimethyl-9H-fluorene, dimethylbenzofluorene, 9,9-diphenyl-9H- Lt; / RTI > and the like.
  • L ' is a single bond;
  • fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60 may be selected from the group consisting of.
  • R a and R b are independently of each other hydrogen; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; may be selected from the group consisting of.
  • the rings formed by bonding of R a ' , R b' , R c ' , R a , R b , Ar 1' to Ar 4 ' , L' and adjacent groups to each other are respectively deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20
  • the formula (A) may be represented by one of the following formulas (B) to (D).
  • the above formula (A) may be represented by one of the following formulas (E) to (G).
  • the formula (A) may be represented by one of the following formulas (H) to (K).
  • R a ' , R b' , R c ' , l', m ', n' and Ar 1 ' to Ar 3' are as defined in formula A above.
  • X is independently of each other O, S or C (R ') (R ").
  • R d ', R e', R ' and R are each independently of the others hydrogen; heavy hydrogen; halogen; alkynyl of C 2 -C 20;; C 2 -C 20 alkenyl group of; C C 1 -C 20 alkyl group an aryl group of 6 -C 20; fluorenyl group; a C 3 -C 20; O, N , S, Si , and a heterocyclic group of C 2 -C 20 containing at least one heteroatom selected from the group consisting of P
  • a fused ring group of a C 3 to C 60 aliphatic ring and a C 6 to C 60 aromatic ring, and neighboring groups may combine with each other to form a ring.
  • the ring may be a C 6 to C 60 aromatic ring, a C 2 to C 60 hetero ring, a C 3 to C 60 aliphatic ring, or a C If three or may be a fused ring of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60, R 'and R "combine to each other to form a ring, they are compounds with a spy combined C It can be formed.
  • o ' is independently an integer of 0 to 3
  • p' is independently an integer of 0 to 4
  • o ' is an integer of 2 or more
  • plural R d' s are the same or different from each other
  • p ' The plurality of R e 's may be the same or different from each other.
  • the rings formed by combining R d ' , R e' , R ', R "and adjacent groups may be substituted with deuterium, halogen, C 1 -C 20 alkyl or C 6 -C 20 aryl, hwandoen silane group; siloxane group; a boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkyl group or a C 6 aryl group a substituted or unsubstituted phosphine oxide -C 20 group; C 1 -C Import of 20 alkylthio; alkyl group of C 1 -C 20;; C 1 -C 20 alkoxyl group alkynyl of C 2 -C 20;; an aryl group of C 6 -C 20 C 2 -C 20 alkenyl group of; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, a
  • formula (A) is represented by one of the following formulas (L) to (O):
  • R e ' , R f ' , R g ' , R h' and R 1 ' are each independently of the other hydrogen; heavy hydrogen; halogen; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; And C 3 ⁇ fused ring group of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60; is selected from the group consisting of, and may form a ring adjacent to each other a group bonded to each other.
  • the ring is C 6 to C 60
  • An aromatic ring of C 2 to C 60 a C 3 to C 60 aliphatic ring, or a fused ring of a C 3 to C 60 aliphatic ring and a C 6 to C 60 aromatic ring.
  • each R f ' , each R g' , each R h ' and each R l' may be the same or different from each other.
  • b ' is an integer of 0 to 3;
  • the ring formed by combining R e ' , R f' , R g ' , R h' and R 1 ' and neighboring groups is a group selected from the group consisting of deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; A phosphine oxide group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A C
  • the compound represented by Formula 20 may be one of the following compounds, but is not limited thereto.
  • the compound represented by the above formula (A) may be one of the following compounds, but is not limited thereto.
  • the present invention provides an organic electronic device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is a one- A single compound or two or more compounds.
  • the present invention provides an organic electronic device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, Species alone compound or two or more compounds.
  • the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer.
  • the compound represented by the formula (A) may be included in the luminescent auxiliary layer, particularly the green luminescent auxiliary layer.
  • the present invention provides an electronic device including a display device including an organic electronic device including a compound represented by Formula 1 or Formula A, and a controller for driving the display device.
  • the compound represented by Formula 1 according to the present invention can be prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
  • Sub 1 of Scheme 1 may be synthesized by the reaction path of Scheme 2, but is not limited thereto.
  • the compounds belonging to Sub 1 include, but are not limited to, the following.
  • the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1.
  • Sub 2 of Scheme 1 may be synthesized by the reaction path of Scheme 3, but is not limited thereto.
  • the compounds belonging to Sub 2 are the same as the following compounds, but are not limited thereto, and the FD-MS values for the following compounds are shown in Table 2.
  • Sub 1-1 (60 g, 133.35 mmol) is added to a round bottom flask and dissolved in THF (489 mL). Subsequently, Sub 2-3 (58.28 g, 160.01 mmol), Pd (PPh 3 ) 4 (6.16 g, 5.33 mmol), K 2 CO 3 (55.29 g, 400.04 mmol) and water (244 mL) And the mixture is refluxed with stirring. After completion of the reaction, the reaction mixture was extracted with ether and water, and the organic layer was dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 73.40 g of a product. (Yield: 75%).
  • the compound represented by Formula 12 according to the present invention can be prepared by reacting Sub 3 with Sub 4-1 as shown in Reaction Schemes 4-1 and 4-2, but is not limited thereto.
  • the compound represented by formula (20) according to the present invention can be prepared as follows but is not limited thereto.
  • the compound represented by formula (A) according to the present invention is prepared by reacting Sub a and Sub b as shown in the following reaction formula (5), but is not limited thereto.
  • Reaction Scheme 5 can be synthesized by the reaction route of the following Reaction Scheme 5-1, but is not limited thereto.
  • Sub b in Scheme 5 may be synthesized by the reaction pathway of Scheme 5-2, but is not limited thereto.
  • N 1 on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -phenylbenzene -1,4-diamine (abbreviated as " 2-TNATA " hereinafter) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.
  • 4,4-bis [N- (Hereinafter abbreviated as " NPD ") was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • the compound 1-1 of the present invention was used as a dopant material in tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) 3 " To form a light emitting layer with a thickness of 30 nm.
  • BAlq (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum
  • BAlq 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 to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic electroluminescent device was prepared in the same manner as in Example 1 except that the compound of the present invention described in Table 5 was used instead of the compound 1-1 of the present invention as a host material of the light emitting layer.
  • An organic electroluminescent device was fabricated in the same manner as in Example 1, except that one of the following Compounds 1 to 3 was used in place of Compound 1-1 of the present invention as a host material of the light emitting layer.
  • a forward bias DC voltage was applied to the organic electroluminescent devices manufactured by Examples 1 to 15 and Comparative Examples 1 to 3 of the present invention, and electroluminescence (EL) characteristics were measured with a photoresearch PR-650 And T95 lifetime was measured by a Mac Science Inc. lifetime measuring device at a luminance of 5000 cd / m 2 .
  • the measurement results are shown in Table 8 below.
  • Comparative Example 4 a mixture of the above-mentioned Comparative Compound 2 and the compound 5-27 of the present invention was used (Comparative Example 4), or Comparative Compound 3 and 5- 27 was used as the organic electroluminescent device, the organic electroluminescent device was fabricated in the same manner as in Example 1 above.
  • the forward bias DC voltage was applied to the organic electroluminescent devices manufactured in Examples 16 to 55 and Comparative Example 4 and Comparative Example 5, and electroluminescence (EL) characteristics were measured with a photoresearch PR-650 And T95 lifetime was measured by a Mac Science Inc. lifetime measuring device at a luminance of 5000 cd / m 2 .
  • the measurement results are shown in Table 9 below.
  • 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injecting layer
  • NPD was vacuum-deposited to a thickness of 60 nm on the hole injecting layer to form a hole transporting layer
  • Compound 14-69 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer
  • Compound 1-1 (first host) and Compound 5- 27 (second host) at a weight ratio of 95: 5 was used as a host material and Ir (ppy) 3 ) as a dopant material to form a light emitting layer with a thickness of 30 nm.
  • BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic electroluminescent device was fabricated in the same manner as in Example 56 except that the compound shown in the following Table 7 was used as the luminescent auxiliary layer material and the first host material.
  • An organic electroluminescence device was fabricated in the same manner as in Example 56 except that Comparative Compound 2 or Comparative Compound 3 was used as the first host material of the light emitting layer.
  • the forward bias DC voltage was applied to the organic electroluminescent devices manufactured in Examples 56 to 73 and Comparative Example 6 and Comparative Example 7 to determine electroluminescence (EL) characteristics with a photoresearch PR-650 And T95 lifetime was measured by a Mac Science Inc. lifetime measuring device at a luminance of 5000 cd / m 2 .
  • the measurement results are shown in Table 10 below.
  • 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer.
  • the compound 14-69 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer Thereby forming a hole transporting layer.
  • the compound 14-72 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer, and the compound 1-1 (first host) and 5- 27 (second host) at a weight ratio of 95: 5 was used as a host material and Ir (ppy) 3 ) as a dopant material to form a light emitting layer with a thickness of 30 nm.
  • BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic electroluminescent device was fabricated in the same manner as in Example 74 except that the compound shown in the following Table 8 was used as the luminescent auxiliary layer material and the first host material.
  • Embodiments of the present invention 74 to Example 85 was applied with a forward bias DC voltage to the organic electroluminescence device manufactured by was measured electroluminescence (EL) properties picture Research (photoresearch)'s PR-650, 5000cd / m 2 basis
  • EL electroluminescence
  • photoresearch photoresearch
  • Comparative Compound 2 differs in that the heteroatom of both side hetero rings bonded to triazine is S while Comparative Compound 3 has heteroatom O.
  • the LUMO value is the highest (Comparative Compound 2) and the LUMO value is lowest when O is introduced (Comparative Compound 3)
  • L is introduced as a heteroatom in one hetero ring and O is introduced in the other hetero ring, the LUMO value is located in the middle.
  • the comparative compound 2 which has the highest LUMO level
  • this LUMO level acts as a barrier to electron transport because the LUMO level is too high. Therefore, the electron transfer from the electron transporting layer to the light emitting layer is not easy, and the charge balance in the light emitting layer is reduced.
  • the energy gap between the electron transporting layer and the LUMO level becomes excessively large, and electrons can not move smoothly from the electron transporting layer to the light emitting layer, .
  • the compound of the present invention in which the LUMO level is located in the middle of the LUMO level of these comparative compounds is used as the phosphorescent host material, it has a LUMO level suitable for electron transport, Can be supplemented. Therefore, when the compound of the present invention is used as a phosphorescent host material, the charge balance in the light emitting layer is increased and the luminous efficiency and lifetime of the organic electroluminescence device are improved.
  • the device results of the examples of the present invention show that when 1-dibenzofuran is substituted for 4-dibenzofuran, performance is improved in all aspects of driving, efficiency and lifetime. It can be seen that when the substituent is substituted at the position, the performance is improved in all aspects of driving, efficiency and lifetime.
  • Example 5 the device result of Example 5 in which 1-dibenzofuran was substituted for triazine compared to Example 1 in which 4-dibenzofuran was substituted for triazine was superior, and it was found that 2-substituted dibenzofuran benzene It was confirmed that the electrical characteristics of the device of Example 7 in which the substituent was bonded at the position of the terminal was improved.
  • Example 1 Example 2, Example 5 and Example 6 of the present invention
  • the substituent bonded to the heterocycle (dibenzofuran, dibenzothiophen) bonded to triazine (Ar 2 , Ar 3 ) are mutually asymmetric, it is confirmed that the device performance is further improved. It is considered that when Ar 2 and Ar 3 are mutually asymmetric, the charge is appropriately localized due to the non-planarity of the compound and the flow of the conjugate system is effectively controlled, thereby improving the lifetime of the device.
  • 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injecting layer
  • NPD was vacuum-deposited to a thickness of 60 nm on the hole injecting layer to form a hole transporting layer
  • the compound G-1 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form a light-emission assisting layer
  • 4,4'-N, N'-dicarbazole- Phenyl hereinafter referred to as CBP
  • Ir (ppy) 3 ) as a dopant material in a weight ratio of 95: 5 to form a 30 nm thick light emitting layer.
  • BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic electroluminescent device was prepared in the same manner as in Example 86 except that the compound of the present invention described in Table 12 was used instead of the compound G-1 of the present invention as the luminescent auxiliary layer material.
  • An organic electroluminescent device was fabricated in the same manner as in Example 86 except that no light-emitting auxiliary layer was formed.
  • An organic electroluminescent device was fabricated in the same manner as in Example 86, except that the following Comparative Compounds ref 1 to ref 4 were used instead of Compound G-1 of the present invention as the luminescent auxiliary layer material.
  • a forward bias DC voltage was applied to the thus fabricated organic EL devices of Examples 86 to 116 and Comparative Examples 12 to 16 to measure electroluminescence (EL) characteristics with PR-650 of a photoresearch company And the T95 lifetime was measured through a life measuring instrument manufactured by Mac Science Inc. at a luminance of 5000 cd / m 2 .
  • the measurement results are shown in Table 12 below.
  • Ref 1, Ref 3 and Ref 4 differ in the substituents which are connected to the nitrogen atom of the amine group in the NPB type.
  • Ref 1 has a phenyl derivative (biphenyl) bonded to the nitrogen atom of the amine group, and Ref 3 and Ref 4 differ in that diphenylfluorene is connected to the nitrogen atom.
  • the device characteristics of Comparative Example 13, Comparative Example 15, and Comparative Example 16 using these compounds as the light-emitting auxiliary layer material are better than those of Comparative Example 13 and Comparative Example 13.
  • Comparative Example 14 when Ref 2 is compared with Ref 4, Ref 4 has one more amine group than Ref 2, and carbazole is bonded to this additional amine group.
  • the device characteristics of Comparative Example 14 and Comparative Example 16 using these compounds as the light emitting auxiliary layer material were similar to each other in terms of efficiency and lifetime, but it was confirmed that the driving voltage of Comparative Example 14 was superior.
  • Example 86 When the results of Example 86, Example 90, Example 91 and Example 97 of the present invention are compared, when a specific substituent other than a simple aryl group is substituted for the substituent of the amine group, the driving voltage, efficiency, and lifetime In the case of the present invention.
  • Example 91 dibenzofurane or fluorene-substituted compound (G-27 or G-52) substituted with a heteroatom was more preferable than Example 86 in which compound G-1 in which a simple phenyl group was substituted with an amine group was used as a light- ), And the compound G-29 in which fluorine and dibenzofuran were connected to one nitrogen atom of an amine group more than Example 90 and Example 97 It can be confirmed that the device result of Example 91 is more excellent.
  • Example 100 Comparing Example 100 and Example 105 of the present invention, it was confirmed that the compound G-101 in which fluorine is substituted for a nitrogen atom connected to diphenylfluorene, It can be confirmed that the characteristics of the device of Example 100 using the compound G-66 in which the fluorine is substituted for the nitrogen atom of the other amine group other than the connected nitrogen source are further improved.
  • Example 86 and Example 102 of the present invention when two amine groups of the compound of the present invention are bonded to each other by a linker, a compound wherein two amine groups are bound to the linker phenyl at the meta position
  • the device results of Example 86 using G-1 as the light-emitting auxiliary layer material show improved device results than Example 102 using Compound G-74 in which two amine groups are para-bonded to phenyl. This is because the structure of the compound is changed according to the substituent type, substitution position and substitution method, and the physical properties of the compound are changed, and the physical properties are changed so as to improve the characteristics of the device when the luminescent auxiliary layer is formed.

Landscapes

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

Abstract

L'invention concerne : un composé représenté par la formule chimique 1 ou par la formule chimique A; un élément électronique organique comprenant une première électrode, une seconde électrode, et une couche organique entre la première électrode et la seconde électrode, et un dispositif électronique comprenant l'élément électronique organique. En comprenant le composé représenté par la formule chimique 1 ou la formule chimique A dans la couche organique, l'élément électronique organique peut présenter une tension d'attaque réduite et une efficacité lumineuse et une durée de vie améliorées
PCT/KR2018/009503 2017-09-29 2018-08-20 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci Ceased WO2019066250A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201880063772.6A CN111164079B (zh) 2017-09-29 2018-08-20 有机电气元件用化合物、利用其的有机电气元件及其电子装置
CN202310194478.1A CN116120192A (zh) 2017-09-29 2018-08-20 有机电气元件用化合物、利用其的有机电气元件及其电子装置
US16/652,383 US11450808B2 (en) 2017-09-29 2018-08-20 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US17/346,936 US20220278285A1 (en) 2017-09-29 2021-06-14 Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
US18/946,259 US20250089557A1 (en) 2017-09-29 2024-11-21 Compound for organic electric element, organic electric element comprising the same, and electronic device thereof

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR20170127537 2017-09-29
KR10-2017-0127537 2017-09-29
KR1020180039162A KR20190038254A (ko) 2017-09-29 2018-04-04 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR10-2018-0039162 2018-04-04
KR1020180072472A KR20190038278A (ko) 2017-09-29 2018-06-25 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR10-2018-0072472 2018-06-25

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US16/652,383 A-371-Of-International US11450808B2 (en) 2017-09-29 2018-08-20 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US17/346,936 Division US20220278285A1 (en) 2017-09-29 2021-06-14 Compound for organic electric element, organic electric element comprising the same, and electronic device thereof

Publications (1)

Publication Number Publication Date
WO2019066250A1 true WO2019066250A1 (fr) 2019-04-04

Family

ID=65901566

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/009503 Ceased WO2019066250A1 (fr) 2017-09-29 2018-08-20 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci

Country Status (2)

Country Link
KR (1) KR102555743B1 (fr)
WO (1) WO2019066250A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102143580B1 (ko) * 2019-08-23 2020-08-12 엘티소재주식회사 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
CN112105614A (zh) * 2018-07-09 2020-12-18 株式会社Lg化学 化合物和包含其的有机发光器件
JP2021001169A (ja) * 2019-06-24 2021-01-07 エルティー・マテリアルズ・カンパニー・リミテッドLT Materials Co., Ltd. ヘテロ環化合物およびこれを用いた有機発光素子
CN112802969A (zh) * 2019-11-14 2021-05-14 三星Sdi株式会社 有机光电子器件及显示器件
CN112979623A (zh) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 一种五元杂环基化合物及其制备方法，有机电致发光器件及元件
WO2021137565A1 (fr) * 2019-12-30 2021-07-08 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, son procédé de fabrication et composition pour couche organique
WO2021182833A1 (fr) * 2020-03-09 2021-09-16 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021206502A1 (fr) * 2020-04-09 2021-10-14 주식회사 엘지화학 Élément électroluminescent organique
KR20210125940A (ko) * 2020-04-09 2021-10-19 주식회사 엘지화학 유기 발광 소자
CN114207859A (zh) * 2019-08-02 2022-03-18 德山新勒克斯有限公司 有机电子器件
EP4019505A1 (fr) * 2020-12-24 2022-06-29 LT Materials Co., Ltd. Composé hétérocyclique, dispositif électroluminescent organique le comprenant, son procédé de fabrication et composition de couche de matériau organique de dispositif électroluminescent organique
EP3972001A4 (fr) * 2020-03-11 2022-07-27 LG Chem, Ltd. Dispositif électroluminescent organique
CN114867722A (zh) * 2019-12-26 2022-08-05 Lt素材株式会社 杂环化合物、包括其的有机发光二极管以及用于有机发光二极管的有机层的组成物
JP2022539023A (ja) * 2019-06-28 2022-09-07 サムスン エスディアイ カンパニー，リミテッド 有機光電子素子用化合物、有機光電子素子用組成物、有機光電子素子および表示装置
JP2022544344A (ja) * 2019-08-16 2022-10-18 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
WO2023096405A1 (fr) * 2021-11-26 2023-06-01 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11997921B2 (en) 2020-09-10 2024-05-28 Lg Chem, Ltd. Organic light emitting device
EP4253378A4 (fr) * 2021-02-22 2024-05-29 Lg Chem, Ltd. Nouveau composé et dispositif électroluminescent organique le comprenant

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022086168A1 (fr) * 2020-10-20 2022-04-28 주식회사 엘지화학 Dispositif électroluminescent organique
CN114230562B (zh) * 2021-11-08 2023-07-14 陕西莱特迈思光电材料有限公司 杂环化合物及包含其的电子元件和电子装置
KR102760306B1 (ko) * 2022-02-14 2025-02-04 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1769269A (zh) * 2005-09-29 2006-05-10 复旦大学 封端的三芳基胺和咔唑类材料、处理方法及其应用
JP2007059750A (ja) * 2005-08-26 2007-03-08 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用材料
KR20120129733A (ko) * 2011-05-20 2012-11-28 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
CN105218541A (zh) * 2015-10-23 2016-01-06 上海道亦化工科技有限公司 一种磷光主体化合物及其有机电致发光器件
US20160343941A1 (en) * 2015-05-19 2016-11-24 Feng-wen Yen Indenotriphenylene-based diamine derivative and organic electroluminescence device using the same
KR101857632B1 (ko) * 2018-02-02 2018-05-14 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
KR101959821B1 (ko) * 2017-09-15 2019-03-20 엘티소재주식회사 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007059750A (ja) * 2005-08-26 2007-03-08 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用材料
CN1769269A (zh) * 2005-09-29 2006-05-10 复旦大学 封端的三芳基胺和咔唑类材料、处理方法及其应用
KR20120129733A (ko) * 2011-05-20 2012-11-28 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
US20160343941A1 (en) * 2015-05-19 2016-11-24 Feng-wen Yen Indenotriphenylene-based diamine derivative and organic electroluminescence device using the same
CN105218541A (zh) * 2015-10-23 2016-01-06 上海道亦化工科技有限公司 一种磷光主体化合物及其有机电致发光器件
KR101857632B1 (ko) * 2018-02-02 2018-05-14 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112105614A (zh) * 2018-07-09 2020-12-18 株式会社Lg化学 化合物和包含其的有机发光器件
CN112105614B (zh) * 2018-07-09 2023-11-10 株式会社Lg化学 化合物和包含其的有机发光器件
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US12048242B2 (en) 2019-05-31 2024-07-23 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
JP2021001169A (ja) * 2019-06-24 2021-01-07 エルティー・マテリアルズ・カンパニー・リミテッドLT Materials Co., Ltd. ヘテロ環化合物およびこれを用いた有機発光素子
JP7226817B2 (ja) 2019-06-24 2023-02-21 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを用いた有機発光素子
JP7303336B2 (ja) 2019-06-28 2023-07-04 サムスン エスディアイ カンパニー，リミテッド 有機光電子素子用化合物、有機光電子素子用組成物、有機光電子素子および表示装置
JP2022539023A (ja) * 2019-06-28 2022-09-07 サムスン エスディアイ カンパニー，リミテッド 有機光電子素子用化合物、有機光電子素子用組成物、有機光電子素子および表示装置
CN114207859A (zh) * 2019-08-02 2022-03-18 德山新勒克斯有限公司 有机电子器件
US12225819B2 (en) 2019-08-02 2025-02-11 Duk San Neolux Co., Ltd. Organic electronic device
JP2022544344A (ja) * 2019-08-16 2022-10-18 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
JP7671504B2 (ja) 2019-08-16 2025-05-02 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
CN112420964B (zh) * 2019-08-23 2025-11-07 Lt素材株式会社 有机发光装置、用于制造其的方法以及用于有机材料层的组合物
KR102143580B1 (ko) * 2019-08-23 2020-08-12 엘티소재주식회사 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
US11785844B2 (en) 2019-08-23 2023-10-10 Lt Materials Co., Ltd. Organic light emitting device, method for manufacturing same and composition for organic material layer
CN112420964A (zh) * 2019-08-23 2021-02-26 Lt素材株式会社 有机发光装置、用于制造其的方法以及用于有机材料层的组合物
CN112802969B (zh) * 2019-11-14 2024-12-13 三星Sdi株式会社 有机光电子器件及显示器件
CN112802969A (zh) * 2019-11-14 2021-05-14 三星Sdi株式会社 有机光电子器件及显示器件
CN114867722B (zh) * 2019-12-26 2025-06-06 Lt素材株式会社 杂环化合物、包括其的有机发光组件以及用于有机发光组件的有机材料层的组成物
CN114867722A (zh) * 2019-12-26 2022-08-05 Lt素材株式会社 杂环化合物、包括其的有机发光二极管以及用于有机发光二极管的有机层的组成物
CN114846010A (zh) * 2019-12-30 2022-08-02 Lt素材株式会社 杂环化合物、包含其的有机发光装置、其制造方法及用于有机层的组成物
TWI877284B (zh) * 2019-12-30 2025-03-21 南韓商Ｌｔ素材股份有限公司 雜環化合物、包含其的有機發光裝置及其製造方法以及用於有機發光裝置的有機層的組成物
WO2021137565A1 (fr) * 2019-12-30 2021-07-08 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, son procédé de fabrication et composition pour couche organique
JP7774309B2 (ja) 2019-12-30 2025-11-21 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、これを含む有機発光素子、その製造方法及び有機物層用組成物
JP2023508847A (ja) * 2019-12-30 2023-03-06 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物、これを含む有機発光素子、その製造方法及び有機物層用組成物
CN113939508A (zh) * 2020-03-09 2022-01-14 株式会社Lg化学 新型化合物及包含其的有机发光器件
WO2021182833A1 (fr) * 2020-03-09 2021-09-16 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
EP3972001A4 (fr) * 2020-03-11 2022-07-27 LG Chem, Ltd. Dispositif électroluminescent organique
US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
CN114144902A (zh) * 2020-04-09 2022-03-04 株式会社Lg化学 有机发光器件
CN114144902B (zh) * 2020-04-09 2024-10-15 株式会社Lg化学 有机发光器件
KR102576736B1 (ko) * 2020-04-09 2023-09-08 주식회사 엘지화학 유기 발광 소자
KR20210125940A (ko) * 2020-04-09 2021-10-19 주식회사 엘지화학 유기 발광 소자
WO2021206502A1 (fr) * 2020-04-09 2021-10-14 주식회사 엘지화학 Élément électroluminescent organique
US11997921B2 (en) 2020-09-10 2024-05-28 Lg Chem, Ltd. Organic light emitting device
EP4019505A1 (fr) * 2020-12-24 2022-06-29 LT Materials Co., Ltd. Composé hétérocyclique, dispositif électroluminescent organique le comprenant, son procédé de fabrication et composition de couche de matériau organique de dispositif électroluminescent organique
EP4253378A4 (fr) * 2021-02-22 2024-05-29 Lg Chem, Ltd. Nouveau composé et dispositif électroluminescent organique le comprenant
CN112979623B (zh) * 2021-02-22 2022-09-09 吉林奥来德光电材料股份有限公司 一种五元杂环基化合物及其制备方法，有机电致发光器件及元件
CN112979623A (zh) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 一种五元杂环基化合物及其制备方法，有机电致发光器件及元件
WO2023096405A1 (fr) * 2021-11-26 2023-06-01 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

Also Published As

Publication number Publication date
KR20190038303A (ko) 2019-04-08
KR102555743B1 (ko) 2023-07-14

Similar Documents

Publication Publication Date Title
WO2019066250A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci
WO2021112403A1 (fr) Élément électronique organique comprenant un composé organique, et dispositif électronique le comprenant
WO2020032424A1 (fr) Élément électronique organique comprenant, en tant que matériau hôte, un mélange de différents types de composés, et dispositif électronique associé
WO2020116816A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2021020942A1 (fr) Élément électroluminescent organique
WO2020116822A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et appareil électronique associé
WO2020141949A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021029616A1 (fr) Dispositif électroluminescent organique
WO2016167491A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique
WO2016122150A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé
WO2013081315A1 (fr) Composé pour un dispositif électronique organique, dispositif électronique organique comprenant celui-ci et dispositif électronique comprenant le dispositif électronique organique
WO2015041428A1 (fr) Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé
WO2015182872A1 (fr) Composé pour élément électro-organique, et élément électro-organique et dispositif électronique utilisant celui-ci
WO2019139419A1 (fr) Diode électroluminescente organique
WO2013122364A2 (fr) Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci
WO2018182294A1 (fr) Composé à base de benzocarbazole et dispositif électroluminescent organique comprenant celui-ci
WO2020130392A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2017010726A1 (fr) Élément électronique organique utilisant un composé comme élément électronique organique et dispositif électronique associé
WO2017030307A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et appareil électronique comprenant celui-ci
WO2015115756A1 (fr) Composé destiné à un élément électrique organique, élément électrique organique ayant recours à ce composé, et dispositif électronique correspondant
WO2021020946A1 (fr) Élément électroluminescent organique
WO2013108997A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique et appareil électronique le comprenant
WO2020130394A1 (fr) Élément électrique organique comprenant un composé pour élément électrique organique et dispositif électronique l'utilisant
WO2011145876A2 (fr) Composé organique hybride innovant et dispositif électroluminescent organique l'utilisant
WO2019135665A1 (fr) Dispositif électroluminescent organique

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: 18860017

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: 18860017

Country of ref document: EP

Kind code of ref document: A1