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WO2014054914A2 - Dérivé d'anthracène et diode électroluminescente organique le comprenant - Google Patents

Dérivé d'anthracène et diode électroluminescente organique le comprenant Download PDF

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WO2014054914A2
WO2014054914A2 PCT/KR2013/008895 KR2013008895W WO2014054914A2 WO 2014054914 A2 WO2014054914 A2 WO 2014054914A2 KR 2013008895 W KR2013008895 W KR 2013008895W WO 2014054914 A2 WO2014054914 A2 WO 2014054914A2
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anthracene derivative
aryl
light emitting
compound
mono
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WO2014054914A3 (fr
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김윤희
권순기
이윤지
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Gyeongsang National University GNU
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    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
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    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D209/56—Ring systems containing three or more rings
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    • C07—ORGANIC CHEMISTRY
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    • 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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Definitions

  • the present invention relates to a novel anthracene derivative and an organic light emitting device comprising the same in a light emitting layer. More specifically, the anthracene derivative according to the present invention relates to an asymmetric, highly warped anthracene compound.
  • LCD Liquid Crystal Display
  • OLED organic light-emitting diodes
  • OLED is a self-luminous type that does not require backlight, and the response speed is faster than LCD in almost all aspects such as fast and low DC driving voltage, wide viewing angle, light weight, and flexible display possibility. It has been attracting attention and recently it is recognized as a core technology of display with the application of technology. However, there are still problems in efficiency and color purity, so it is urgent to develop a blue organic light emitting material for easier practical use of OLED.
  • the structure of an organic EL device is generally an anode, a hole injection layer (HIL), a hole transfer layer (HTL), an emission layer (EML), an electron transfer layer (ETL) ), An electron injection layer (EIL), and a cathode, which are formed by thermal evaporation under high vacuum (10 -6 to 10 -7 Torr). .
  • the light emitting mechanism first injects holes in the anode and electrons in the cathode, and they meet in the light emitting layer to form unstable excitons. This unstable excitons stabilize and release energy, which is released as light energy.
  • the light emitting material is also important, but it is also essential that electrons and holes must meet in the light emitting layer, and thus the role of injecting and transferring electrons and holes is also important.
  • the color of light emitted from the OLED is determined by the difference in energy level between HOMO and LUMO of the light emitting material.
  • the energy spacing between HOMO-LUMO can be controlled by varying the conjugation length of the molecule using the Linear Combination of Atomic Orbital (LCAO) method.
  • LCAO Linear Combination of Atomic Orbital
  • OLEDs need three primary colors of light: red, green, and blue to display all the colors of nature.
  • the development of high-efficiency blue light emission has become a problem for the practical use of OLED, which has a problem in that the blue light emitting material deteriorates the performance of the entire device due to the low color purity and lifetime compared to other materials.
  • the present invention relates to an anthracene derivative, and more particularly, has a high thermal stability, optical properties and chemical stability by substituting a substituent that can give a high degree of distortion in the molecule of the anthracene derivative, and minimizes intramolecular or intermolecular interactions.
  • the purpose is to provide an anthracene derivative that can have a high luminous efficiency.
  • Another object of the present invention is to provide an anthracene derivative having the characteristics of high color purity and high luminous efficiency including the anthracene derivative and an organic light emitting device including the same as a light emitting material (a blue light emitting material and a blue fluorescent host).
  • it may include an anthracene derivative of the formula (1).
  • R 1 to R 4 are independently selected from hydrogen, C 1 -C 30 alkyl or C 6 -C 30 aryl, at least one selected from R 1 and R 4 and at least one selected from R 2 and R 3 C 1 -C 30 alkyl or C 6 -C 30 aryl,
  • X and Y are independently of each other hydrogen, C 6 -C 30 aryl or C 6 -C 30 heteroaryl containing one or more elements selected from N, O, S, wherein aryl or N, O, Heteroaryls comprising at least one element selected from S are C 1 -C 30 alkyl, C 6 -C 30 aryl, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino, phenane And may be further substituted with one or more selected from trill, indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofuranyl or pyrenyl.
  • the present invention also includes an anthracene derivative of the formula (2).
  • X and Y are the same as defined in Formula 1, and R 2 and R 4 are each independently C 1 -C 30 alkyl or C 6 -C 30 aryl.
  • X and Y are each independently phenyl, biphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofu Ranyl or pyrenyl, wherein X and Y are C 1 -C 30 alkyl, C 6 -C 30 aryl, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino, phenanthryl, Anthracene derivatives which may be further substituted with one or more selected from indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofuranyl or pyrenyl.
  • the present invention also relates to anthracene derivatives comprising the following compounds.
  • Another aspect of the present invention relates to an organic light emitting device including an light emitting layer between an anode, a cathode, and a positive electrode, and to an organic light emitting device including an anthracene derivative according to the present invention in a light emitting layer.
  • the present invention also relates to an organic light emitting device using the anthracene derivative according to the present invention as a host material.
  • the present invention relates to a novel asymmetric anthracene derivative, including an anthracene derivative of the formula (1), more specifically an anthracene derivative of the formula (2).
  • R 1 to R 4 are independently selected from hydrogen, C 1 -C 30 alkyl or C 6 -C 30 aryl, at least one selected from R 1 and R 4 and at least one selected from R 2 and R 3 C 1 -C 30 alkyl or C 6 -C 30 aryl,
  • X and Y are independently of each other hydrogen, C 6 -C 30 aryl or C 6 -C 30 heteroaryl containing one or more elements selected from N, O, S, wherein aryl or N, O, Heteroaryls comprising at least one element selected from S are C 1 -C 30 alkyl, C 6 -C 30 aryl, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino, phenane And may be further substituted with one or more selected from trill, indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofuranyl or pyrenyl, thiazolyl or thidiazolyl.
  • X and Y are the same as defined in Chemical Formula 1, and R 2 and R 4 may be each independently C 1 -C 30 alkyl or C 6 -C 30 aryl. More specifically, in Formula 2, X and Y are each independently phenyl, biphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofuranyl or Pyrenyl, mono or di-phenylaminophenyl, wherein X and Y are C 1 -C 30 alkyl, C 6 -C 30 aryl, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 It may be further substituted with one or more selected from arylamino, phenanthryl, indenyl, acenaphthyl, thienyl, carbazolyl, dibenz
  • Anthracene derivatives of the present invention may be specifically exemplified as the following compounds, but the following compounds do not limit the present invention.
  • Anthracene derivatives according to the invention may be prepared according to Scheme 1, for example.
  • X is phenyl, biphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, indenyl, acenaphthyl, thienyl, carbazolyl, dibenzofuranyl or pyrenyl, mono or di-phenyl Aminophenyl, wherein X and Y are C 1 -C 30 alkyl, C 6 -C 30 aryl, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino, phenanthryl, indenyl One or more selected from acenaphthyl, thienyl, carbazolyl or dibenzofuranyl, pyrenyl.
  • an organic light emitting device including an light emitting layer between an anode, a cathode, and a positive electrode, the organic light emitting device comprising the anthracene derivative according to the present invention in a light emitting layer.
  • the anthracene derivative according to the present invention is a light emitting material having a hole transporting capability, and has an advantage of increasing quantum efficiency, lowering driving voltage, and increasing luminous efficiency.
  • the anthracene derivative according to the present invention may have a highly twisted structure due to the high rotational disturbance of the anthracene group and the substituent, thereby exhibiting a high glass transition temperature and suppressing the interaction between the anthracene molecules as much as possible, resulting in a high color purity emission spectrum. Can be.
  • the OLED including the anthracene derivative according to the present invention has a problem of deterioration due to driving heat generated during driving of the device and a problem of deterioration of emission characteristics and color purity due to low purity and pi-stacking of the material for forming an organic film. It is possible to provide an electroluminescent device of high efficiency and high color purity due to the fact that the luminous efficiency is improved, the stability of the device is improved, and the intermolecular interference due to the strong distortion is reduced.
  • the anthracene derivative according to the present invention has an asymmetric structure, exhibits a highly twisted structure with high rotational disturbances of anthracene groups and substituents, thereby exhibits a high glass transition temperature, and the interaction between anthracene molecules is suppressed as much as possible, resulting in a high color purity emission spectrum. Indicates. Therefore, the OLED formed with the organic layer such as the light emitting layer using the asymmetric anthracene derivative according to the present invention solves the problem of heat generated during driving, the low purity of the organic film forming material, the deterioration of the emission characteristics and the color purity due to ⁇ -stacking.
  • the asymmetric anthracene derivative according to the present invention can be used as a host material of a conventionally known blue fluorescent material.
  • the OLED of the present invention can realize excellent blue color purity.
  • FIG. 3-A graph showing the UV absorption and the PL spectrum of the liquid state of Compound 1 prepared in Preparation Example 1 and the PL spectrum of the solid state.
  • Example 8 is an organic electroluminescent device according to Example 1 [ITO / 2TANATA (40 nm) / NPB (35 nm) / Compound 1 (30 nm) / B3PYMPM (15 nm) / LiF (1 nm) / Al (100 nm) ] Structure.
  • FIG. 9 is a graph showing current-voltage-luminance of the organic electroluminescent device according to Example 1 and Comparative Example 1.
  • FIG. 10 is a graph showing an external quantum efficiency according to current of an organic electroluminescent device according to Example 1 and Comparative Example 1.
  • FIG. 10 is a graph showing an external quantum efficiency according to current of an organic electroluminescent device according to Example 1 and Comparative Example 1.
  • FIG. 11 is a graph showing normalized EL and color coordinates of an organic electroluminescent device according to Example 1 and Comparative Example 1.
  • FIG. 11 is a graph showing normalized EL and color coordinates of an organic electroluminescent device according to Example 1 and Comparative Example 1.
  • FIG. 13 is a graph showing current-voltage-luminance of the organic electroluminescent device according to Example 2 and Comparative Example 2.
  • FIG. 14 14-a graph showing external quantum efficiency (External Quantum Efficiency) according to current of an organic electroluminescent device according to Example 2 and Comparative Example 2.
  • FIG. 14 14-a graph showing external quantum efficiency (External Quantum Efficiency) according to current of an organic electroluminescent device according to Example 2 and Comparative Example 2.
  • FIG. 15 is a graph showing normalized EL and color coordinates of an organic electroluminescent device according to Example 2 and Comparative Example 2.
  • FIG. 15 is a graph showing normalized EL and color coordinates of an organic electroluminescent device according to Example 2 and Comparative Example 2.
  • an anthracene derivative according to the present invention a method for preparing the same, and a luminescent property of a device are described for the detailed understanding of the present invention, but only for the purpose of illustrating the embodiments of the present invention. It does not limit the scope of.
  • the thermal properties were measured by thermogravimetric analysis (TGA) and differential calorimetry (DSC) by heating from 40 ° C. to 700 ° C. at 10 ° C. per minute under a nitrogen atmosphere.
  • TGA thermogravimetric analysis
  • DSC differential calorimetry
  • Anthracene derivatives were prepared at a concentration of 10 ⁇ 5 M to measure UV-VIS and PL spectra.
  • Anthracene derivatives were prepared at a concentration of 10 ⁇ 5 M and measured by cyclic voltammetry.
  • J-V-L Device current-voltage-luminance measurements were measured with a Spectro radiometer (Photo Research (o.PR-650) -source meter (Kethley 2400)).
  • the transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from the OLED glass was patterned to 2 mm ⁇ 2 mm, and then ultrasonic cleaning was performed sequentially using trichloroethylene, acetone, ethanol, and distilled water. And stored in isopropanol and used.
  • An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF; Lithium Fluoride) to a thickness of 1 nm as an electron injection layer and depositing Al on the electron injection layer to form a cathode of 100 nm.
  • LiF lithium fluoride
  • the organic electroluminescent device manufactured was [ITO / 2TANATA (40 nm) / NPB (35 nm) / Compound 1 (30 nm) / B3PYMPM (15 nm) / LiF (1 nm) / Al (100 nm)] from below It has a stacked structure in order.
  • the transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from the OLED glass was patterned to be 2 mm ⁇ 2 mm, and then ultrasonic cleaning was performed sequentially using trichloroethylene, acetone, ethanol, and distilled water. And stored in isopropanol and used.
  • compound 1 prepared in Preparation Example 1 was used as a host on the hole transport layer, and 6MDPA (N, N-diphenyl-N ′, N′-dim-tolyl-SBFF-5,9-diamine), known as a dopant, was used. 30 nm was deposited as a light emitting layer.
  • 6MDPA N, N-diphenyl-N ′, N′-dim-tolyl-SBFF-5,9-diamine
  • Bis-4.6 is disposed on the emission layer.
  • An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF; Lithium Fluoride) to a thickness of 1 nm as an electron injection layer and depositing Al on the electron injection layer to form a cathode of 100 nm.
  • LiF lithium fluoride
  • the organic electroluminescent device manufactured was [ITO / 2TANATA (60 nm) / NPB (35 nm) / Compound 1: 6MDPA (30 nm, 5 wt) / B3PYMPM (20 nm) / LiF (1 nm) / Al (100 nm )] Has a stacked structure from below.
  • the transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from the OLED glass was patterned to be 2 mm ⁇ 2 mm, and then ultrasonic cleaning was performed sequentially using trichloroethylene, acetone, ethanol, and distilled water. And stored in isopropanol and used.
  • An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF; Lithium Fluoride) to a thickness of 1 nm as an electron injection layer and depositing Al on the electron injection layer to form a cathode of 100 nm.
  • the organic electroluminescent device manufactured was [ITO / 2TANATA (40 nm)) / NPB (35 nm) / MADN (30 nm) / B3PYMPM (15 nm) / LiF (1 nm) / Al (100 nm)] It has a stacked structure in order.
  • the transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from the OLED glass was patterned to be 2 mm ⁇ 2 mm, and then ultrasonic cleaning was performed sequentially using trichloroethylene, acetone, ethanol, and distilled water. And stored in isopropanol and used.
  • 6MDPA also known as dopant
  • MADN 2-methyl-9,10-di (2-naphthyl) anthracene
  • N N-diphenyl-N ', N'-dim-tolyl-SBFF-5,9-diamine
  • 2-methyl-9,10-di (2-naphthyl) anthracene MADN; 2-methyl-9,10-di (2-napthyl) anthracene
  • 6MDPA N, N-diphenyl-N ′, N′-dim-tolyl-SBFF-5,9-diamine
  • Methylpyrimidine (B3PYMPM; bis-4,6- (3,5-di-3-pyridylphenyl) -2-methylpyrimidine) was deposited to an electron transport layer at a thickness of 20 nm.
  • An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF; Lithium Fluoride) to a thickness of 1 nm as an electron injection layer and depositing Al on the electron injection layer to form a cathode of 100 nm.
  • the organic electroluminescent device manufactured was [ITO / 2TANATA (60 nm) / NPB (35 nm) / MADN: 6MDPA (30 nm, 5 wt%) / B3PYMPM (20 nm) / LiF (1 nm) / Al (100 nm )] Has a stacked structure from below.
  • Example 1 The results of evaluating the current-voltage, luminance-voltage, and color characteristics of the organic electroluminescent device manufactured in Example 1 and the organic electroluminescent device manufactured in Comparative Example 1 are shown in FIGS. 9 to 11, and in Example 1
  • the evaluation results of the fabricated organic electroluminescent device showed color purity close to deep blue with color coordinates of (0.154,0.048). The maximum efficiency was 4.59%, which showed excellent luminous efficiency.
  • the anthracene derivative according to the present invention has an asymmetric structure, exhibits a highly twisted structure with high rotational disturbances of anthracene groups and substituents, thereby exhibits a high glass transition temperature, and the interaction between anthracene molecules is suppressed as much as possible, resulting in a high color purity emission spectrum. Indicates. Therefore, the OLED formed with the organic layer such as the light emitting layer using the asymmetric anthracene derivative according to the present invention solves the problem of heat generated during driving, the low purity of the organic film forming material, the deterioration of the emission characteristics and the color purity due to ⁇ -stacking.
  • the asymmetric anthracene derivative according to the present invention can be used as a host material of a conventionally known blue fluorescent material.
  • the OLED of the present invention can realize excellent blue color purity.

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PCT/KR2013/008895 2012-10-04 2013-10-04 Dérivé d'anthracène et diode électroluminescente organique le comprenant Ceased WO2014054914A2 (fr)

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US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
CN113105382A (zh) * 2021-03-26 2021-07-13 华南理工大学 一种联苯修饰咔唑基团的蒽基深蓝光材料及其制备与应用

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DE102007024850A1 (de) * 2007-05-29 2008-12-04 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
KR101495547B1 (ko) * 2008-04-17 2015-02-25 롬엔드하스전자재료코리아유한회사 신규한 전자 재료용 화합물 및 이를 포함하는 유기 전자소자
KR101216004B1 (ko) * 2009-08-17 2012-12-27 에스에프씨 주식회사 안트라센 유도체 및 이를 포함하는 유기전계발광소자
KR101145685B1 (ko) * 2010-02-26 2012-05-24 경상대학교산학협력단 안트라센 유도체 및 이를 포함하는 유기 발광 소자
KR20110123701A (ko) * 2010-05-07 2011-11-15 에스에프씨 주식회사 안트라센계 화합물 및 이를 포함하는 유기전계발광소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
CN113105382A (zh) * 2021-03-26 2021-07-13 华南理工大学 一种联苯修饰咔唑基团的蒽基深蓝光材料及其制备与应用

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