WO2020103294A1 - Matériau électroluminescent micromoléculaire organique et composant électroluminescent organique - Google Patents

Matériau électroluminescent micromoléculaire organique et composant électroluminescent organique

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WO2020103294A1
WO2020103294A1 PCT/CN2018/124982 CN2018124982W WO2020103294A1 WO 2020103294 A1 WO2020103294 A1 WO 2020103294A1 CN 2018124982 W CN2018124982 W CN 2018124982W WO 2020103294 A1 WO2020103294 A1 WO 2020103294A1
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organic
light
adamantane
small molecule
organic electroluminescent
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PCT/CN2018/124982
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Chinese (zh)
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吴元均
矫士博
史婷
苏仕健
李伟
李彬彬
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深圳市华星光电技术有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • the invention relates to the field of organic electroluminescence, in particular to an organic small molecule luminescent material and an organic electroluminescent device using the organic small molecule luminescent material.
  • OLED Organic electroluminescence
  • the principle of the organic electroluminescent device is that under the action of an electric field, holes and electrons are injected from the anode and the cathode, respectively, through the hole injection layer, the hole transport layer and the electron injection layer, the electron transport layer, formed in the light-emitting layer recombination Excitons, exciton radiation decays and glows.
  • organic electroluminescent materials As the core component of organic electroluminescent devices, organic electroluminescent materials have a great influence on the performance of the devices. Among them, high quantum efficiency fluorescence characteristics, good semiconductor characteristics, high-quality film-forming characteristics, good chemical stability and thermal stability, good processing performance, etc. are its main performance factors. According to the molecular structure characteristics, it is classified according to the emission wavelength range, including organic small molecule light-emitting materials, organic complex light-emitting materials and organic polymer light-emitting materials.
  • organic complex luminescent materials are basically heavy metal complexes, the production cost is high, which is not conducive to large-scale production, and there is a serious efficiency roll-off phenomenon in organic complex luminescent materials under high current density
  • the stability of the organic complex luminescent materials is not good, and compared with polymer materials, organic small molecule luminescent materials have fewer preparation steps, stable structure, and convenient purification, so they can obtain higher device efficiency , So that it is more likely to be commercialized.
  • flexible OLED devices made with small organic light-emitting materials have received great attention because of their unparalleled advantages, and have made tremendous progress.
  • Organic light-emitting diodes have made great progress so far, and scientists have proposed various theories to explain the mechanism of light emission.
  • organic small-molecule photoelectric materials with simple structures, good performance, and commercialization requirements are still very limited, and the development of new organic photoelectric materials still has a pivotal significance.
  • the object of the present invention is to provide a small organic light-emitting material that has a very high photoluminescence quantum yield in a thin-film state and is a light-emitting guest material with good electron-hole dual-transport properties.
  • Another object of the present invention is to provide an organic electroluminescent device.
  • the light-emitting layer uses the above-mentioned organic small molecule light-emitting material, which has high external quantum efficiency and excellent light-emitting performance.
  • the present invention provides a small organic light-emitting material using 10H-spiro [acridine-9,2'-adamantane] as the donor unit, which is obtained by coupling the acceptor unit and the donor unit Of luminescent materials;
  • Ar is an aromatic substituent having electron-deficient properties.
  • the organic small molecule luminescent material consists of 2,4,6-triphenyltriazine, 2,4,6-triphenylpyrazine, 1,3-phthalonitrile and 3,5-phthalonitrile , Diphenylphosphono, diphenylsulfone, phenoxazine-10,10'-dioxide, tris (2,6-xylyl) boron, thioanthracene-5,5,10,10-tetraoxide
  • the substance, 9-thioxanthone or 9-zanthone is the acceptor unit.
  • the small organic light-emitting material is prepared by the donor unit 10H-spiro [acridine-9,2'-adamantane] and the acceptor unit as raw materials through a Hartwig-Buchwald coupling reaction.
  • 10H-spiro [acridine-9,2'-adamantane] is prepared from aniline, o-bromoiodobenzene and adamantone, which are prepared by Hartwig-Buchwald coupling reaction and (Boc) 2 O plus protection reaction in this order .
  • the present invention also provides an organic electroluminescent device, which includes a light-transmitting substrate, an anode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode layer that are stacked;
  • the light emitting layer contains the organic small molecule light emitting material as described above.
  • the small organic light-emitting material serves as a light-emitting guest material in the light-emitting layer.
  • the light-emitting layer includes one or more of the organic small molecule light-emitting materials having different structural formulas.
  • the light-emitting layer is prepared by thermal evaporation, spin coating, brush coating, spray coating, dip coating, roll coating, printing, or inkjet printing.
  • the organic small molecule luminescent material of the present invention is composed of a novel acridine donor unit 10H-spiro [cridine-9,2'-adamantane] based on a non-aromatic rigid structure adamantane, Coupling with the acceptor unit, its structure is single, the molecular weight is determined, it is easy to purify, and the reproducibility of multiple synthesis is good, with a low sublimation temperature and a high decomposition temperature, the film morphology is stable, due to the donor unit 10H-spiro [ Acridine-9,2'-adamantane] has a very rigid structure, a non-aromatic rigid structure adamantane as part of the donor structure, this small organic light-emitting material has a very high photoluminescence quantum yield in the state of thin film Rate, when used in organic electroluminescent devices, it can effectively solve the problem of low efficiency of excited molecules due to configuration relaxation resulting in severe non-radi
  • FIG. 1 is a thermogravimetric analysis diagram of molecule 1 prepared in Example 7;
  • Figure 2 is the absorption spectra of molecules 1, 2, 3 and 4 prepared in Examples 7, 8, 9 and 10 in toluene solution;
  • FIG. 3 is a fluorescence emission spectrum of molecules 1, 2, 3, and 4 prepared in Examples 7, 8, 9, and 10 in a toluene solution;
  • Example 4 is a graph of current density-voltage-luminance curve of an organic electroluminescent device using molecule 1 prepared in Example 7 as a guest material of a light-emitting layer;
  • Example 5 is a graph of current efficiency-luminance relationship of an organic electroluminescent device using molecule 1 prepared in Example 7 as a guest material of a light-emitting layer;
  • Example 6 is a graph showing the relationship between the external quantum efficiency and brightness of an organic electroluminescent device using the molecule 1 prepared in Example 7 as a guest material of a light-emitting layer;
  • Example 7 is a light emission spectrum of an organic electroluminescence device using molecule 1 prepared in Example 7 as a guest material of a light emitting layer;
  • 10 is a graph showing the relationship between the external quantum efficiency and the brightness of an organic electroluminescent device using the compound DMAc-TRZ as the light-emitting layer guest material;
  • FIG. 11 is a light emission spectrum of an organic electroluminescence device using the compound DMAc-TRZ as a guest material of a light emitting layer.
  • the invention provides an organic small molecule luminescent material, adopting a new type of acridine donor unit 10H-spiro [cridine-9,2'-adamantane] based on non-aromatic rigid structure adamantane, through Hartwig- Buchwald coupling reaction luminescent material obtained by coupling the donor unit 10H-spiro [acridine-9,2'-adamantane] with the acceptor unit.
  • 10H-spiro [acridine-9,2'-adamantane] is obtained through a series of simple reactions such as Hartwig-Buchwald reaction, (Boc) 2 O plus protection reaction, low temperature reaction, normal temperature or high temperature ring closure reaction, Its chemical structural formula is
  • adamantane Since the inherent rigid structure of adamantane can increase the rigidity of the entire molecule, it can effectively reduce the energy loss caused by the geometric configuration deformation of the small organic light-emitting molecule composed of it in the excited state, so the donor unit 10H is used -
  • the organic small molecule luminescent material obtained by spiro [acridine-9,2'-adamantane] has a very high photoluminescence quantum yield in a thin film state, which in turn helps to improve the efficiency and stability of the device.
  • Ar is an aromatic substituent having electron-deficient properties.
  • the small organic light-emitting material is 2,4,6-triphenyltriazine, 2,4,6-triphenylpyrazine, 1,3-phthalonitrile, 3,5-benzene Dicarbonitrile, diphenylphosphono, diphenylsulfone, phenoxazine-10,10'-dioxide, tris (2,6-xylyl) boron, thioanthracene-5,5,10,10 -Commonly used electron-deficient aromatic compounds and their derivatives such as tetraoxide, 9-thioxanthone, or 9-zanthone are receptor units.
  • Ar may be any organic radical
  • the organic small molecule luminescent material of the present invention consists of a novel acridine donor unit 10H-spiro [cridine-9,2'-adamantane] based on a non-aromatic rigid structure adamantane, coupled with an acceptor unit It has a single structure, a fixed molecular weight, is easy to purify, and has good reproducibility for multiple synthesis. It has a low sublimation temperature and a high decomposition temperature, and the film morphology is stable.
  • the organic small molecule luminescent material obtained by using the donor unit has a very high photoluminescence quantum in the thin film state Yield, when used in organic electroluminescent devices, can effectively solve the problem of low efficiency of the excited state molecules due to configuration relaxation resulting in severe non-radiative attenuation, and can be changed by changing the , 2'-adamantane]
  • the type of acceptor unit connected can adjust the material's luminous color, molecular weight, electrophilicity and other material characteristics, effectively adjust its conjugate length and intramolecular charge transfer, and adjust the highest occupied orbital and The lowest vacant orbital energy level can meet the needs of organic electroluminescent devices, so that it can give the device more excellent performance when applied in organic electroluminescent devices.
  • the present invention also provides an organic electroluminescent device, including a laminated light-transmitting substrate, an anode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode
  • the light-emitting layer contains the organic small molecule light-emitting material described above.
  • the small organic light-emitting material serves as a light-emitting guest material in the light-emitting layer.
  • the light-emitting layer includes one or more of the organic small molecule light-emitting materials having different structural formulas.
  • the light-emitting layer may be prepared by thermal evaporation, spin coating, brush coating, spray coating, dip coating, roll coating, printing, or inkjet printing.
  • the organic small molecule light emitting material used in the light emitting layer couples the donor unit 10H-spiro [cridine-9,2'-adamantane] to the acceptor unit through the Hartwig-Buchwald coupling reaction Obtained, with high external quantum efficiency and excellent light-emitting performance.
  • the solvent was removed by pressure distillation, 100 mL of glacial acetic acid was added, N 2 was passed for 20 minutes, 5 mL of concentrated hydrochloric acid was added, and the mixture was heated to reflux and stirred for 24 hours.
  • the mixture was poured into 500 mL of water, and the product was extracted with dichloromethane.
  • the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed after separation, and it was separated and purified with a silica gel chromatography column to obtain a white solid (1.5 g, 62%).
  • Example 5 By analyzing and comparing the above Example 5 and Example 6, it is found that the reaction method using glacial acetic acid, concentrated hydrochloric acid and heating can effectively promote the progress of the reaction.
  • Example 7 Compared with Example 7, the difference is that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine is replaced with an equimolar amount of 2- (4-bromo Phenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine, other raw materials and steps are the same as in Example 7, and the final yield of the solid product is 75%.
  • Product molecular formula C45H40N4; molecular weight: 636.33; elemental analysis results: C, 84.87; H, 6.33; N, 8.80.
  • Example 7 Compared with Example 7, the difference is that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine is replaced with an equimolar amount of 2- (4-bromo Phenyl) -4,6-bis (2-methylphenyl) -1,3,5-triazine, the other raw materials and steps are the same as in Example 7, and the final yield of the solid product is 75%.
  • Product molecular formula C45H40N4; molecular weight: 636.32; elemental analysis results: C, 84.87; H, 6.30; N, 8.83.
  • Example 7 Compared with Example 7, the difference is that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine is replaced with an equimolar amount of 2- (4-bromo Phenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, other raw materials and steps are the same as in Example 7, and the final yield of the solid product is 65% .
  • Product molecular formula C47H44N4; molecular weight: 664.36; elemental analysis results: C, 84.90; H, 6.67; N, 8.43.
  • the thermal stability of the organic small molecule light-emitting material 1 based on the 10H-spiro [acridine-9,2'-adamantane] donor unit prepared in Example 7 was tested to clarify the molecular stability of the material And the feasibility of applying vacuum evaporation to organic light-emitting devices.
  • the specific implementation steps are as follows: Thermogravimetric analysis (TGA) is measured on Netzsch TG 209, the heating rate is 10 °C min -1 under nitrogen protection, the heating end point is greater than 600 °C, as shown in Figure 1, after testing, molecule 1
  • the thermal decomposition temperature is 420 °C. It has a very high decomposition temperature, it is easy to obtain high-purity photoelectric materials by gradient sublimation, and it is suitable for electroluminescent devices.
  • This example prepares an organic electroluminescent molecule using the organic small molecule luminescent material molecule 1 prepared in Example 7 based on the 10H-spiro [acridine-9,2'-adamantane] donor unit for the luminescent layer guest material Light emitting device, the specific stack structure is as follows:
  • indium tin oxide is the anode
  • TAPC is the hole transport layer
  • TmPyPB is the electron transport layer
  • lithium fluoride is the electron injection layer
  • aluminum is the cathode
  • molecule 1: DPEPO is the light emitting layer.
  • the preparation method is as follows: the transparent conductive indium tin oxide glass substrate is sequentially cleaned with acetone, micron-level semiconductor special detergent, deionized water, and isopropyl alcohol for 15 minutes to remove the dirt on the substrate surface. Then put it in a thermostat at 80 degrees Celsius to dry it for use. The dried indium tin oxide substrate is treated with an oxygen plasma ignition device for 4 minutes to further remove organic contaminants attached to the surface.
  • TAPC, light-emitting layer material, TmPyPB, lithium fluoride, and aluminum are thermally deposited on the light-emitting layer by vacuum thermal evaporation to obtain the organic electroluminescent device of this embodiment.
  • a 10- (4- (4,6-phenyl-1,3,5-triazine-2-yl) phenyl) -9,9-dimethyl-9,10- Dihydroacridine (abbreviated as: DMAc-TRZ) (structure shown below) is used as an organic electroluminescent device for the guest material of the light emitting layer.
  • the specific stacked structure of the organic electroluminescent device is as follows: glass substrate / indium tin oxide (125 nanometers) / TAPC (40 nanometers) / 20wt% or 30wt% Lithium (1 nanometer) / Aluminum (100 nanometers).
  • Indium tin oxide is the anode
  • TAPC is the hole transport layer
  • TmPyPB is the electron transport layer
  • lithium fluoride is the electron injection layer
  • aluminum is the cathode
  • DMAc-TRZ: DPEPO is the light emitting layer.
  • the preparation method of the organic electroluminescent device in this implementation is the same as the method in Example 12.
  • the brightness and radiant energy density of electromechanical light-emitting devices prepared according to Example 12 and Comparative Example 13 at different voltages were tested with a CS-200 spectroradiometer and PR745 spectroscopic instrument. According to the current density and brightness of the organic electroluminescent device at different voltages, the current efficiency and external quantum efficiency (EQE) of the organic electroluminescent device are obtained.
  • EQE external quantum efficiency
  • Example 12 By comparing and analyzing Example 12 and Example 13, the following conclusions can be obtained: under the same device conditions, compared with the molecular DMAc-TRZ, molecule 1 obtains more excellent external quantum efficiency and bluer electroluminescence Spectrum, the reason may be: by replacing the two CH 3 hydrogen atoms of the acridine group, the super conjugate electron donation effect in molecule 1 is effectively reduced.
  • the 10H-spiro [cridine-9,2'- The molecule composed of the adamantane] donor unit has a very rigid molecular structure, which effectively suppresses the relaxation process of the molecular configuration of the molecule under the excited state condition, and reduces the Stokes shift of molecule 1.
  • the two reasons above result in a bluer electroluminescence spectrum.
  • the rigid structure suppresses the non-radiative decay process of the molecule, improves the molecular photoluminescence quantum yield, and thus improves the device based on molecule 1 effectiveness.
  • the organic small molecule light-emitting material of the present invention has a role as a doping guest material in the light-emitting layer. Since blue light-emitting materials are very important for full-color display and white light photos, it is of great significance to prepare high-efficiency blue light materials with application potential.
  • the organic small molecule luminescent material of the present invention consists of a novel acridine donor unit 10H-spiro [cridine-9,2'-adamantane] based on a non-aromatic rigid structure adamantane, and
  • the acceptor unit is coupled, its structure is single, the molecular weight is determined, it is easy to purify, and the reproducibility of multiple synthesis is good. It has a low sublimation temperature and a high decomposition temperature, and the film morphology is stable.
  • Pyridin-9,2'-adamantane has a very rigid structure, a non-aromatic rigid structure adamantane as part of the donor structure, this small organic light-emitting material has a very high photoluminescence quantum yield in the state of thin film , which can effectively solve the problem of low efficiency of excited molecules due to configuration relaxation resulting in severe non-radiative attenuation when applied in organic electroluminescent devices, and can be changed by 10H-spiro [cridine-9,2 '-Adamantane]
  • the type of acceptor unit connected can adjust the material's luminous color, molecular weight, electrophilicity and other material properties, effectively control its conjugation length and intramolecular charge transfer, and adjust the highest occupied orbit and the lowest vacancy Orbital energy level to meet the needs of organic electroluminescent devices, so that when applied in organic electroluminescent devices can give the device more excellent performance.
  • the light-emitting layer uses the above-

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Abstract

La présente invention concerne un matériau électroluminescent micromoléculaire organique et un composant électroluminescent organique. Le matériau électroluminescent micromoléculaire organique est produit par accouplement d'un nouveau motif donneur d'acridine 10H-spiro[acridine-9,2'-adamantane] à un motif récepteur, présente une structure unique et un poids moléculaire déterminé, est pratique à purifier, fournit une grande reproductibilité de synthèse multiple et présente une température de sublimation réduite, une température de décomposition augmentée et une morphologie de film stable. De plus, étant donné que l'adamantane non aromatique et à structure rigide sert de structure d'une partie donneuse, le matériau électroluminescent micromoléculaire organique présente un rendement quantique de photoluminescence extrêmement élevé dans une morphologie de film et, lorsqu'il est appliqué dans le composant électroluminescent organique, résout efficacement le problème d'une faible efficacité de composant suite à une atténuation non radiative grave due à la relaxation de configuration d'une molécule excitée.
PCT/CN2018/124982 2018-11-19 2018-12-28 Matériau électroluminescent micromoléculaire organique et composant électroluminescent organique WO2020103294A1 (fr)

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CN110467536B (zh) 2019-06-14 2020-06-30 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和光电转化器件
CN112441977B (zh) * 2019-09-04 2024-03-19 北京鼎材科技有限公司 化合物、其应用及包含其的有机电致发光器件
CN110724129B (zh) * 2019-10-30 2021-04-20 上海天马有机发光显示技术有限公司 一种有机电致发光化合物及其应用
CN112028918B (zh) * 2019-12-31 2023-04-28 陕西莱特光电材料股份有限公司 一种有机化合物、其应用以及有机电致发光器件
KR20210137594A (ko) * 2020-05-07 2021-11-18 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 발광 소자
KR20210153188A (ko) * 2020-06-09 2021-12-17 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 발광 소자
CN114516829A (zh) * 2022-02-16 2022-05-20 闽都创新实验室 一种二苯乙烯衍生物，其制备及应用

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