WO2011108901A2 - Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci - Google Patents

Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci Download PDF

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WO2011108901A2
WO2011108901A2 PCT/KR2011/001538 KR2011001538W WO2011108901A2 WO 2011108901 A2 WO2011108901 A2 WO 2011108901A2 KR 2011001538 W KR2011001538 W KR 2011001538W WO 2011108901 A2 WO2011108901 A2 WO 2011108901A2
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substituted
unsubstituted
carbon atoms
group
phosphorus
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WO2011108901A9 (fr
WO2011108901A3 (fr
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김대성
박정환
김기원
박용욱
정화순
변지훈
박정근
최대혁
김동하
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덕산하이메탈(주)
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Publication of WO2011108901A3 publication Critical patent/WO2011108901A3/fr
Publication of WO2011108901A9 publication Critical patent/WO2011108901A9/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a spiro carbazole compound containing a spiro skeleton, an organic electronic device using the same, and a terminal thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electronic device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic electronic device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Materials used as the organic material layer in the organic electronic device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electronic device has not been sufficiently achieved, and therefore, the development of a new material is still required.
  • the present inventors have found a spiro carbazole compound containing a spiro skeleton, and the compound has excellent electrical and luminescent properties, so that when applied to organic electronic devices, it has excellent hole injection and hole transport ability under low driving voltage. It has been found to be useful as a hole injection material and a hole transporting material having.
  • an object of the present invention is to provide an aromatic amine compound having various substituents, an organic electronic device using the same, and a terminal thereof.
  • the present invention provides a compound represented by the following formula.
  • the compound according to an embodiment of the present invention provides a spiro carbazole compound including a spiro skeleton.
  • the present invention has an aromatic amine compound having a variety of substituents and organic electronic device using the same, it can play a variety of roles in the terminal, and when applied to the organic electronic device and the terminal has excellent electrical characteristics and light emission characteristics excellent hole under low driving voltage It is useful as a hole injection material and a hole transport material having injection and hole transport ability. The present invention is also useful as a host material for phosphorescent dopants of various colors, depending on the compound. In the case of employing the organic film using the organic electroluminescent compound described above, an organic electronic device having high efficiency, low voltage, high brightness, and long life based on superior current density characteristics can be manufactured.
  • 1 to 5 show examples of organic electronic devices to which the compounds of the present invention can be applied.
  • the present invention provides a compound represented by Formula 1 below.
  • R 1 , R 2 , R 3 and R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 1
  • R a , R b , R c and R d are each independently of each other a hydrogen atom, a halogen atom, a cyano group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 Alkoxy group of 60 to 60, substituted or unsubstituted alkenyl group of 1 to 60 carbon atoms, substituted or unsubstituted arylene group of 5 to 60 carbon atoms, substituted or unsubstituted aryl group of 5 to 60 carbon atoms, substituted or unsubstituted carbon atoms 5 Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur containing at least one aryloxy group, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) of 60 to 60 A substituted or unsubstitute
  • Ar 1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 60 carbon atoms, a substituted or unsubstituted arylene group having 5 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms containing at least one aryl group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si).
  • n is an integer of 1-4.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may combine with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring.
  • the organic material layer of the organic electric device which will be described later, may be formed by the soluble process using the compound.
  • the organic material layer of the organic electronic device is made by using a variety of polymer materials, and less by a solvent process (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method) rather than deposition. It can be prepared in a number of layers.
  • the compound described above may be represented by the following formula (2).
  • the compounds represented by Formula 2 may correspond to specific examples substituted with hydrogen atoms except for a specific position among the compounds represented by Formula 1.
  • Ar 1 is as defined above
  • Ar 2 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 60 carbon atoms, a substituted or unsubstituted arylene group having 5 to 60 carbon atoms, substituted or Substituted or unsubstituted C1 to 50 containing at least one or more unsubstituted aryl group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms or sulfur (S) containing at least one alkyl group or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ), Nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) may be a substituted or unsubstituted C1
  • Ar 1 is as defined above, and R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 to Alkoxy group of 60, substituted or unsubstituted alkenyl group having 1 to 60 carbon atoms, substituted or unsubstituted arylene group having 5 to 60 carbon atoms, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted carbon atoms 5 to 60 A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur containing at least one aryloxy group of 60, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (
  • Ar 1 is as defined above, R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a cyano group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C 1 to 60 An alkoxy group, a substituted or unsubstituted C1-C60 alkenyl group, a substituted or unsubstituted C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C5-C60 A substituted or unsubstituted C1-C50 alkyl group or sulfur (S) containing at least one or more of an aryloxy group, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ), A substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms
  • R 1 , R 2 , R 3 , R 4 , R a , R b , R c and R d , Ar 1 , Ar 2 , R 8 , R 9 may be substituted or unsubstituted.
  • the compounds according to the examples provide spiro carbazole compounds comprising a spiro backbone.
  • Organic electronic devices exist in which the compounds described with reference to Chemical Formulas 1 to 5 are used as the hole injection material and the hole transport material.
  • Organic electronic devices in which the compounds described with reference to Chemical Formulas 1 to 5 may be used include, for example, an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor (organic TFT), and a photo. It may be used in organic semiconductor materials such as diodes, organic lasers, and laser diodes.
  • organic light emitting diodes As an example, among the organic electronic devices to which the compounds described with reference to Chemical Formulas 1 to 5 may be applied, organic light emitting diodes (OLEDs) will be described below. However, the present invention is not limited thereto and the compounds described above may be applied to various organic electronic devices. Can be.
  • Another embodiment of the present invention is an organic electronic device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one layer of the organic material layer comprises an organic electric field comprising the compounds of Formulas 1 to 5 Provided is a light emitting device.
  • the organic electroluminescent device except that at least one layer of the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer to form the compound of Formula 1 to 5 It can be prepared in a structure known in the art using conventional manufacturing methods and materials in the art.
  • the structure of the organic light emitting display device according to the present invention is illustrated in FIGS. 1 to 5, but is not limited thereto.
  • reference numeral 101 denotes a substrate
  • 110 denotes an anode
  • 103 denotes a hole injection layer
  • 104 denotes a hole transport layer
  • 105 denotes a light emitting layer
  • 106 denotes an electron injection layer
  • 107 denotes a cathode.
  • Compounds described with reference to Formulas 1 to 5 may be included on one or more of a hole injection layer and a hole transport layer. Specifically, the compounds described with reference to Formulas 1 to 5 may be used in place of one or more of the hole injection material and hole transport material described below, or may be used by forming a layer with them. Of course, not only used in one layer of the organic layer, but may be used in two or more layers.
  • the organic electroluminescent device is a metal or conductive metal acid on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation It can be prepared by depositing a cargo or an alloy thereof to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed by using a variety of polymer materials, but not by a deposition process (solvent process) such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, etc. It can be prepared as a layer.
  • the organic electroluminescent device may form an organic layer, for example, a light emitting layer, by the soluble process of the compounds described above.
  • the substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
  • An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon.
  • the positive electrode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methyl thiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrins, oligothiophenes, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacrido ne-based organics, and perylene-based organics.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer positioned thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • applications for vehicle body display require heat resistance to the device, and materials having a glass transition temperature (Tg) of 70 ° C. or higher are preferred.
  • Tg glass transition temperature
  • the materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicone Germanium oxide compounds, silicon arylamine compounds and the like.
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • the light emitting material is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4 '-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-d iphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and perylene, BczVBi (3,3) A small amount of '[(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole (
  • DCJTB [2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H
  • a small amount of doping such as -benzo (ij) quinolizin-9-yl) etheny l] -4H-pyran-4-ylidene] -propanedinitrile
  • a polymer of polyphenylene vinylene (PPV) system or a polymer such as poly fluorene may be used for the organic light emitting layer. .
  • the compounds described with reference to Chemical Formulas 1 to 5 may replace the hole injection layer and the hole transport layer, or may form a corresponding layer together with existing materials, and may be used as host materials of phosphorescent dopants of various colors depending on the compound. It may be formed.
  • the electron transport layer is positioned on the organic light emitting layer.
  • Such an electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and efficiently transporting the injected electrons.
  • it should be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons.
  • the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the cathode is positioned on the electron transport layer. This cathode serves to inject electrons into the electron transport layer.
  • a metal having a low work function is more preferable for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
  • the organic light emitting display device may be a top emission type, a bottom emission type, or a double-sided emission type according to the material used.
  • the present invention includes a display device including the organic electronic device described above, and a terminal including a control unit for driving the display device.
  • This terminal refers to current or future wired and wireless communication terminals.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as PDA, electronic dictionary, PMP, remote control, navigation, game machine, various TV, various computers.
  • 2-Bromobiphenyl was dissolved in anhydrous THF solvent, the reaction temperature was lowered to 78 ° C., and t-Butyllithum was slowly added dropwise and stirred for 1 hour.
  • the intermediate B synthesized in step 1) was dissolved in THF solvent and slowly added dropwise, followed by stirring for 12 hours. After completion of the reaction, the mixture was extracted with Ethyl acetate, a small amount of water in the reaction was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and separated by column chromatography to obtain the desired intermediate B (yield). : 54%).
  • the intermediate C synthesized in step 3) was dissolved in anhydrous THF, the reaction temperature was lowered to 78 ° C., n-BuLi (1.6 M in hexane) was slowly added dropwise, and the reaction was stirred for 30 minutes. The temperature of the reaction was lowered to 78 ° C. and Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwise. After completion of the reaction, the mixture was extracted with Ethyl acetate, a small amount of water in the reaction was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was recrystallized with Methanol to obtain the desired intermediate D (yield: 71%).
  • CuPc copper phthalocyanine
  • a-NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • BD-052X is a blue fluorescent dopant
  • an organic light emitting diode was manufactured using 9,10-di (naphthalen-2-yl) anthracene (ADN) as a light emitting host material.
  • an organic electroluminescent device having the same structure as the test example was manufactured by using a compound represented by Chemical Formula 6 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.
  • CBP Chemical Formula 6
  • the organic light emitting diodes of Experimental Examples 1 to 3 exhibit substantially the same color coordinates compared to the organic light emitting diodes using CBP as a host material and have improved luminous efficiency with critical significance. It can be seen that.
  • a compound represented by the following Chemical Formula 7 (hereinafter abbreviated as a-NPB) was used as a hole transport layer material, thereby fabricating an organic light emitting display device having the same structure as in the test example.
  • Table 2 summarizes the physical properties of the organic electroluminescent device of Comparative Example 2 and the organic electroluminescent device of Experimental Example using a-NPD as the hole injection layer material.
  • the organic light emitting diodes of Experimental Examples 4 and 5 exhibit substantially the same color coordinates as the organic EL devices using a-NPB as the hole transport layer material, and have a driving voltage and a current density. Therefore, it can be seen that the luminous efficiency is improved with a critical significance.
  • the compounds of the present invention have excellent electrical and luminescent properties, and when used in an organic light emitting device as a hole injection material and a hole transport material, based on improvements in physical characteristics such as driving voltage, current density, and luminous efficiency, High efficiency, low voltage, high brightness and long life can be expected.
  • improvements in physical characteristics such as driving voltage, current density, and luminous efficiency, High efficiency, low voltage, high brightness and long life can be expected.
  • green and blue light emission of long life is obtained, it is used as a green phosphorescent host material and a hole transport layer material of the organic light emitting display device, and thus it is possible to remarkably improve the luminous efficiency and lifetime.
  • the compounds of the present invention can achieve the same effect even when used in other organic material layers of the organic light emitting device.
  • the compounds represented by Formulas 1 to 5 are substituted or unsubstituted of R 1 , R 2 , R 3 , R 4 , R a , R b , R c and R d , Ar 1 , Ar 2 , R 8 , R 9
  • the substituents described above are illustrative examples of some of the compounds represented by the formula (5) in a broad relationship, but compounds represented by the formulas (1) to (4) that are not illustrated by way of example as a comparative example It can be confirmed that the reason for having the parent-nucleus structure of 4 has the same effect as the above-described comparative examples, and the results may form part of the present specification.

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Abstract

L'invention porte sur un composé de spiro-carbazole comprenant un squelette spiro, et sur un élément électronique organique utilisant celui-ci et sur un terminal de celui-ci.
PCT/KR2011/001538 2010-03-05 2011-03-07 Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci WO2011108901A2 (fr)

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KR20140088003A (ko) * 2012-12-31 2014-07-09 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
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CN114213377A (zh) * 2021-12-10 2022-03-22 上海钥熠电子科技有限公司 一种蒽基荧光发光主体材料及其应用

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