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WO2019083167A1 - Élément électroluminescent organique utilisant un composé pour élément électroluminescent organique et dispositif électronique le comprenant - Google Patents

Élément électroluminescent organique utilisant un composé pour élément électroluminescent organique et dispositif électronique le comprenant

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Publication number
WO2019083167A1
WO2019083167A1 PCT/KR2018/011034 KR2018011034W WO2019083167A1 WO 2019083167 A1 WO2019083167 A1 WO 2019083167A1 KR 2018011034 W KR2018011034 W KR 2018011034W WO 2019083167 A1 WO2019083167 A1 WO 2019083167A1
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group
layer
ring
compound
organic electroluminescent
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English (en)
Korean (ko)
Inventor
변윤선
오대환
김대성
박무진
황선필
이선희
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DukSan Neolux Co Ltd
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DukSan Neolux Co Ltd
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    • 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
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Definitions

  • the present invention relates to an organic electroluminescent device using an organic electroluminescent compound 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 field element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic material layer is often formed of a multi-layered structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • 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, Indicating a tendency for the lifetime to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time.
  • a light emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer. It is time to develop.
  • the light emitting auxiliary layer should be formed of a material having a hole mobility, a high T 1 (electron block) value, and a wide band gap so as to have a proper driving voltage capable of solving the problems of the hole transporting layer.
  • a material constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material,
  • the organic material layer for an organic electroluminescent device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and development of materials for the light-emitting auxiliary layer is urgently required.
  • An object of the present invention is to provide an organic electroluminescent device using a compound capable of improving a high luminous efficiency, a low driving voltage, a high heat resistance, a color purity and a lifetime of a device as a light emitting auxiliary layer material, and an electronic device thereof.
  • the present invention provides an organic electroluminescent device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode.
  • the organic material layer includes a light-emission-assisting layer formed between the first electrode and the light-emitting layer, and the light-emission-assisting layer includes a compound represented by the following formula.
  • the present invention provides an electronic device including the organic electroluminescent device.
  • the compound according to an embodiment of the present invention as a light emitting auxiliary layer material, it is possible not only to lower the driving voltage of the organic field effect device, but also to greatly improve the luminous efficiency, color purity and lifetime of the device.
  • FIG. 1 is an illustration of an organic electroluminescent device according to the present invention.
  • organic field element 110 substrate
  • 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.
  • 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.
  • 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.
  • 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 each coupled as follows: and wherein R 1 may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.
  • FIG. 1 is a view illustrating a stacked structure of organic electroluminescent devices according to an embodiment of the present invention.
  • an organic electroluminescent device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a 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, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151 and a buffer layer 141 may be further included, and the electron transporting layer 160 may serve as a hole blocking layer You can do it.
  • the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the compound according to the present invention applied to the organic material layer includes a hole injecting layer 130, a hole transporting layer 140, an electron transporting layer 160, an electron injecting layer 170, a light emitting layer 150, a light efficiency improving layer, And the like.
  • the compound of the present invention can be used as the material of the hole transporting layer 140 and / or the light emitting auxiliary layer 151.
  • the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub-substituents bonded thereto are very important, When the optimal combination of the energy level and T 1 value between each organic material layer and the intrinsic properties (mobility, interfacial characteristics, etc.) of the materials are achieved, long lifetime and high efficiency can be achieved at the same time.
  • the hole transporting layer and / or the light-emitting auxiliary layer using the compound of the present invention, it is possible to optimize the energy level and the T 1 value between the respective organic layers, the mobility of the material, The lifetime and efficiency of the device can be improved at the same time.
  • the 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. Further, a light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150.
  • the organic material layer may be formed by using various polymer materials in 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, a roll- A screen printing process, a thermal transfer process, or the like. 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 one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device, or a device for a quantum dot display.
  • OLED organic electroluminescent
  • OPC organic photoconductor
  • organic TFT organic transistor
  • monochromatic or white illumination device or a device for a quantum dot display.
  • Another embodiment of the present invention may include an electronic device including a display device including the organic electroluminescent 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,
  • the display device may include an organic electroluminescent display, a quantum dot display, and the like.
  • an organic electroluminescent device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode.
  • the organic material layer may include a light emitting auxiliary layer formed between the first electrode and the light emitting layer, and the light emitting auxiliary layer may include a compound represented by the following general formula (1).
  • each symbol may be defined as follows.
  • R a1 , R b1 , R a2 and R b2 are each independently a C 1 to C 50 alkyl group; A C 6 to C 60 aryl group; A fluorenyl group; And a C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;
  • R a1 and R b1 may combine with each other to form a ring, and R a2 and R b2 may also combine with each other to form a ring, for example, a C 6 to C 60 aromatic hydrocarbon; 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 ; Or a combination thereof.
  • R a1 and R b1 and / or R a2 and R b2 may combine with each other to form a C 6 -C 60 ring containing a benzene ring.
  • R a1 , R b1 , R a2 and R b2 are alkyl groups, it is preferably a C 1 -C 10 alkyl group, more preferably a C 1 -C 4 alkyl group, specifically methyl, ethyl, have.
  • R a1 , R b1 , R a2 and R b2 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, naphthalene, biphenyl, terphenyl and the like, and most preferably phenyl.
  • R a1 and R b1 and / or R a2 and R b2 are bonded to each other to form a ring containing a benzene ring, preferably a C 6 to C 21 ring, more preferably a C 6 to C 13 ring
  • R b1 and / or R a2 and R b2 are bonded to each other to form a fused ring of an aromatic ring and an aliphatic ring, preferably a C 3 to C 30 aliphatic ring and a C 6 to C 30 Of fused rings of aromatic hydrocarbons, more preferably fused rings of C 3 to C 18 aliphatic rings and C 6 to C 18 aromatic hydrocarbons.
  • R a1 and R b1 and / or R a2 and R b2 may be bonded to each other to form a dihydroindene or a derivative thereof, a fluorene or a derivative thereof, and consequently share a carbon atom with the pentagonal ring to which they are bonded.
  • a compound can be formed by spiraling.
  • R a1 , R b1 , R a2 and R b2 is a methyl group or phenyl, or R a1 and R b1 are bonded to each other to form a fluorene, a benzofluorene, or a dibenzofluorene, R a2 and R b2 may combine with each other to form fluorene, benzofluorene, or dibenzofluorene.
  • R a1 , R b1 , R a2 and R b2 are both methyl groups, all are phenyl or all may be fluorene, R a1 and R b1 are methyl or phenyl, R a2 and R b2 may form a fluorene ring, or conversely, R a1 and R b1 may form a fluorene ring, and R a2 and R b2 may all be methyl or phenyl.
  • R 1 to R 7 independently from each other 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 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 ') (R "); or neighboring groups may be bonded to each other to form a ring.
  • Neighboring R 1 , adjacent R 2 , neighboring R 3 , neighboring R 4 , neighboring R 5 , neighboring R 6 , and / or neighboring R 7 are combined to form a ring C 6 to C 60 aromatic hydrocarbons;
  • R a1 , R b1 , R a2 and R b2 are independently of each other a C 1 -C 10 alkyl group, a C 6 -C 20 aryl group, or R a1 and R b1 and / or R a2 and R b2 are bonded to each other to form a C 6 to C 21 ring including a benzene ring, and R 1 to R 7 independently of each other are bonded to each other to form a C 6 to C 20 ring containing a benzene ring .
  • R a1, R b1, R a2 and R b2 are independently is an alkyl group of C 1 ⁇ C 4 to each other, C 6 ⁇ , or aryl group of C 18, R a1 and R b1 and / or R a2 and R b2 are bonded to each other to form a C 6 to C 13 ring containing a benzene ring and at least one pair of adjacent groups of R 1 to R 7 are bonded to each other to form a C 6 to C 12 aromatic Hydrocarbons can be formed.
  • R a1, R b1, R a2 and R b2 may have independently a methyl group or a phenyl group, or R a1 and R b1 and / or R a2 and R b2 each other may form a fluoren-bond to one another, R 1 to R group between at least one pair of adjacent of 7 may form a benzene ring bonded to each other.
  • a, c, e and g is an integer of 0 ⁇ 4
  • b, d and f is 0-3 integer and each is 2 or more integer, orally, a plurality of each of a plurality of each of R 1 to these R 7 are each, respectively They may be the same or identical to each other.
  • Ar 1 is a C 6 to C 60 aryl group, preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, biphenyl, terphenyl, naphthyl , Phenanthrene, pyrene, and the like.
  • R a1 , R b1 , R a2 and R b2 independently of one another are a C 1 to C 10 alkyl group or a C 6 to C 20 aryl group , R a1 and R b1 and / or R a2 and R b2 may be bonded to each other to form a C 6 to C 21 ring containing a benzene ring.
  • R a1 , R b1 , R a2 and R b2 independently of one another are a C 1 to C 4 alkyl group or a C 6 to C 18 aryl group Or R a1 and R b1 and / or R a2 and R b2 may combine with each other to form a C 6 -C 13 ring containing a benzene ring.
  • R 1 to R 7 independently of each other are adjacent to each other to form a C 6 to C 20 ring containing a benzene ring
  • Ar 1 is a C 6 to C 18 aryl group
  • at least one pair of adjacent groups of R 1 to R 7 are bonded to each other to form a C 6 to C 12 aromatic hydrocarbon containing a benzene ring .
  • R a1 , R b1 , R a2 and R b2 are independently of each other a C 1 to C 10 alkyl group or a C 6 to C 20 aryl group when R 1 is a C 6 to C 30 aryl group, Or R a1 and R b1 and / or R a2 and R b2 may combine with each other to form a C 6 to C 21 ring containing a benzene ring, and R 1 to R 7 may form, independently of each other, And may be bonded to each other to form a C 6 to C 20 ring containing a benzene ring.
  • R a1 , R b1 , R a2 and R b2 independently of one another are a C 1 to C 4 alkyl group or a C 6 to C 18 aryl group Or R a1 and R b1 and / or R a2 and R b2 may be bonded to each other to form a C 6 to C 13 ring containing a benzene ring, and at least one of R 1 to R 7 adjacent groups And may be bonded to each other to form a C 6 to C 12 aromatic hydrocarbon containing a benzene ring.
  • R a1 , R b1 , R a2 and R b2 are each independently a methyl group or a phenyl group, or R a1 and R b1 and / or R a2 and R b2 are bonded to each other to form fluorene, and R 1 to R 7 At least a pair of adjacent groups may be bonded to each other to form a benzene ring, and Ar 1 may be phenyl, biphenyl, terphenyl, naphthyl, phenanthrene or pyrene.
  • L ' is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene 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 ; And a C 2 to C 60 heterocyclic group.
  • R 'and R are independently selected from C 6 ⁇ aryl group of C 60 to each other; fluorene group; C 3 ⁇ fused ring group of an aromatic ring of C 60 of aliphatic rings and C 6 ⁇ C 60; and O, N, A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from S, Si and P;
  • a ring formed by combining R a1 , R b1 , R a2 , R b2 , R 1 to R 7 , Ar 1 , L ', R', R ", R a1 and R b1 or R a2 and R b2 , And a ring formed by bonding adjacent groups of R 1 to R 7 to each other are each a group selected from the group consisting of deuterium, halogen, a silyl group substituted or unsubstituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; boron group; germanium group; a cyano group; a nitro group; a C 1 -C 20 alkylthio come; alkyl group of C 1 -C 20;; C 1 -C 20 alkoxyl group of the alkenyl group of C 2 -C 20; C 2 alkynyl of -C 20; an aryl group of C 6 -
  • Ar 1 may be further substituted with aryl groups such as phenyl, biphenyl, terphenyl, naphthyl, etc., or deuterium, methyl, ethene, methoxy, F, CN,
  • the compound represented by Formula 1 may be one of the following compounds.
  • the compound represented by the general formula (1) may be contained in the luminescent auxiliary layer in the form of a single compound or a mixture of two or more kinds, more preferably as a material of the luminescent auxiliary layer of the luminescent auxiliary layer .
  • an electronic device including a display device including an organic electroluminescent device, and a control unit for driving the display device, wherein the organic electroluminescent device comprises: ≪ / RTI >
  • the compound represented by Formula 1 according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.
  • Sub 1 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 2, but is not limited thereto.
  • the compound belonging to Sub 1 produced by the above synthesis method may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.
  • the compounds belonging to Sub 2 may be, but not limited to, the following compounds, and Table 2 shows FD-MS values of the compounds belonging to Sub 2.
  • 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 (hereinafter abbreviated as "2-TNATA”) was vacuum-deposited to form a hole injection layer having a thickness of 60 nm, and then N, N'-bis (1-naphthalenyl) bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as "NPB”) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • NPB N'-bis (1-naphthalenyl) bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
  • Compound P-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.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • BAlq aluminum (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum
  • BAlq 2,3-bis (2-methyl-8-quinolinolato aluminum
  • Alq 3 &quot Tris- (8-hydroxyquinoline) aluminum
  • Alq 3 &quot LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to form a cathode.
  • An organic electroluminescence device was prepared 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 of the luminescent auxiliary layer.
  • An organic electroluminescence device was fabricated in the same manner as in Example 1 except that no luminescent auxiliary layer was formed.
  • An organic electroluminescence device was prepared in the same manner as in Example 1, except that one of the following Comparative Compounds A to D was used in place of the compound P-1 of the present invention as a material of the luminescent auxiliary layer.
  • An organic electroluminescent device was prepared in the same manner as in Example 1 except that the compound P-1 of the present invention was used as a material of the hole transport layer and NPB was used as a material of the luminescent auxiliary layer.
  • Electruminescence (EL) characteristics were measured with photoresearch PR-650 by applying a forward bias DC voltage to the organic EL devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 6 of the present invention was measured at a luminance of 5000 cd / m < 2 > through a life measuring apparatus manufactured by Mac Science Inc., and T95 lifetime was measured.
  • Comparative Compound A and Comparative Compound B differ only in the position where the amine group is bonded to dibenzofurane.
  • the amine group is bonded to the 1-position of dibenzofurane
  • the comparative compound B is the amine group Is bonded to the 4-position of dibenzofurane.
  • the device characteristics of Comparative Example 2 and Comparative Example 3 using these compounds as the light emitting auxiliary layer material were better than those of Comparative Example 3.
  • Comparative Compound C differs in that both amine groups are in a non-linear position (i.e., the amine group is bonded to the meta position of the phenyl).
  • the device characteristics of Comparative Example 3 and Comparative Example 4 using these compounds as the light emitting auxiliary layer material were remarkably improved in Comparative Example 4 using Comparative Compound C.
  • Comparative Example 4 when comparing the comparative compound C with the comparative compound D, the comparative compound C has phenyl bonded to the nitrogen of the amine group bonded with the dibenzofuran, while the comparative compound D has the dimethylfluorene bonded thereto.
  • the device characteristics of Comparative Example 4 and Comparative Example 5 using these compounds as the light-emitting auxiliary layer material were slightly improved in the device characteristics of Comparative Example 5.
  • the characteristics of the device can be varied depending on the substitution position of the substituent, the kind of the substituent, and the like. It seems that the physical properties of the compound during compound deposition in the manufacturing process act as a major factor (eg, energy balance) in improving the device performance.

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

Abstract

L'invention concerne : un élément électroluminescent organique comprenant un composé représenté par la formule chimique 1 à titre de matériau de couche électroluminescente auxiliaire ; et un dispositif électronique le comprenant, où la couche électroluminescente auxiliaire comprend le composé représenté par la formule chimique 1, ce qui permet d'abaisser une tension de commande de l'élément électroluminescent organique et d'améliorer son rendement électroluminescent et sa durée de vie.
PCT/KR2018/011034 2017-10-24 2018-09-19 Élément électroluminescent organique utilisant un composé pour élément électroluminescent organique et dispositif électronique le comprenant Ceased WO2019083167A1 (fr)

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KR10-2017-0138253 2017-10-24

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CN113563203A (zh) * 2021-07-30 2021-10-29 上海钥熠电子科技有限公司 基于间苯二胺的化合物及其在有机电致发光显示器件中的应用
CN114957188A (zh) * 2021-02-26 2022-08-30 阜阳欣奕华材料科技有限公司 化合物与有机电致发光器件以及中间体化合物
US11807615B2 (en) * 2019-10-28 2023-11-07 Wuhan Tianma Micro-Electronics Co., Ltd. Compound, organic electroluminescent device, and display device

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