WO2016150193A1 - Matériau électroluminescent organique et dispositif préparé à l'aide de celui-ci - Google Patents

Matériau électroluminescent organique et dispositif préparé à l'aide de celui-ci Download PDF

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Publication number
WO2016150193A1
WO2016150193A1 PCT/CN2015/096421 CN2015096421W WO2016150193A1 WO 2016150193 A1 WO2016150193 A1 WO 2016150193A1 CN 2015096421 W CN2015096421 W CN 2015096421W WO 2016150193 A1 WO2016150193 A1 WO 2016150193A1
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carbon atoms
group
substituted
unsubstituted
compound
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PCT/CN2015/096421
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English (en)
Chinese (zh)
Inventor
高春吉
崔敦洙
汪康
孙毅
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吉林奥来德光电材料股份有限公司
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Publication of WO2016150193A1 publication Critical patent/WO2016150193A1/fr

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    • 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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D401/14—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 three or more hetero 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
    • 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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Specifically, it relates to novel aromatic compounds as electroluminescent materials and uses them as an organic electroluminescent device.
  • An organic electroluminescent device generally consists of two opposing electrodes and at least one layer of an organic luminescent compound interposed between the two electrodes. Charge is injected into the organic layer formed between the anode and the cathode to form electron and hole pairs, causing light emission of an organic compound having fluorescent or phosphorescent properties.
  • OLED Organic electroluminescent device
  • the host material in the electroluminescent device mainly has two types of small molecule host materials and polymer host materials.
  • Many high-efficiency electroluminescent devices have been prepared by doping a phosphorescent complex with a small molecule host material as a light-emitting layer.
  • the preparation of small molecule electroluminescent devices requires complex processes such as vacuum evaporation, which greatly increases the manufacturing cost.
  • the nature of the small molecule itself is easy to crystallize and the stability of the device is greatly limited.
  • the preparation of electroluminescent devices by doping various phosphorescent complex guest bodies with a polymer host material as a light-emitting layer has received much attention.
  • the technology of the present invention is a technology related to organic electro-device materials.
  • representative materials of hole transport materials in organic electro-devices are as follows:
  • the characteristics of the currently required materials are that the material has thermal stability and rapid hole mobility, and the high efficiency and long life of the illuminant.
  • the present invention provides a material superior in performance to the present stage.
  • the invention provides a hole transporting material with good luminous efficiency, which connects a biscarbazole and an ether compound together, increases the mobility of holes, and prepares the new aromatic amine compound into a device. Very good luminous efficiency.
  • L 1 is an integer of 0 to 2
  • Ar 1 is an aryl group having 6 to 30 carbon atoms (arylene group when L 1 > 0, but does not include a benzo compound)
  • Ar 2 is a carbon number.
  • R 1 to R 4 represent the same or different hydrogen atoms, substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, substituted or unsubstituted aralkyloxy groups having 7 to 50 carbon atoms, substituted or unsubstituted a substituted aralkyl fluorenyl group having 7 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic ring having 5 to 50 carbon atoms, and a substituted or unsubstituted carbon atom having 6 to 30 carbon atoms.
  • Aromatic amines Aromatic amines.
  • the biscarbazole derivative is a novel aromatic amine compound specific to any one of the following Chemical Formula 2-1 to Chemical Formula 2-5:
  • L 1 is an integer of 0 to 2
  • Ar 1 is an aryl group having 6 to 30 carbon atoms (arylene group when L 1 >0)
  • Ar 2 is a carbon atom number 7 ⁇ 50 aralkyl group, aralkyloxy group having 7 to 50 carbon atoms, aralkyl fluorenyl group having 7 to 50 carbon atoms, aryl group having 6 to 50 carbon atoms, heterocyclic ring having 5 to 50 carbon atoms, A substituted or unsubstituted aromatic amine having 6 to 30 carbon atoms.
  • R 1 to R 4 represent a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 50 carbon atoms, and a substituted or unsubstituted carbon atom number of 7 to 50.
  • the chemical formula 1 includes a specific new aromatic amine compound specific to any one of the following Chemical Formulas 3-1 to 3-8:
  • Ar 2 is an aralkyl group having 7 to 50 carbon atoms, an aralkyloxy group having 7 to 50 carbon atoms, an aralkyl fluorenyl group having 7 to 50 carbon atoms, or carbon.
  • L 1 is an integer of 0 to 2
  • R 1 to R 4 represent the same or different hydrogen atoms, substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, and substituted or unsubstituted carbon atoms 7 to 50.
  • R 1 to R 4 are selected from any one of the following chemical formulae to constitute a specific new aromatic amine compound:
  • X and Y independently represent an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, and a substitution.
  • an unsubstituted aralkyloxy group having 7 to 30 carbon atoms a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, or a substituted or unsubstituted A substituted heterocyclic group having 5 to 30 carbon atoms or a substituted or unsubstituted aromatic amine having 6 to 30 carbon atoms.
  • the chemical formula 1 described above can be expressed as any one of the following chemical formulas 4-1 to 4-6 to represent a specific new aromatic Aromatic amine compound.
  • L 1 is an integer of 0 to 2.
  • Ar 1 is an aryl group having 6 to 30 carbon atoms (arylene group when L 1 >0, but does not include a benzo compound), and
  • Ar 2 is an aralkyl group having 7 to 50 carbon atoms and 7 to 7 carbon atoms. a aralkyloxy group of 50, an aralkyl fluorenyl group having 7 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heterocyclic ring having 5 to 50 carbon atoms, or a substituted or unsubstituted carbon atom having 6 to 30 carbon atoms; Aromatic amines.
  • the specific expression form is at least Selected from the following groups, respectively
  • One of 138 new compounds is formed with the above Chemical Formulas 4-1 to 4-6, that is, the compounds of the compounds E to J in the specification examples.
  • Compounds E to J are specific structural forms of the compound, but the series of compounds are not limited to the chemical structures listed. Any combination of R 1 to R 4 , Ar 1 , Ar 2 , and L 1 within the above protective range should be included in the chemical formula 1.
  • Another aspect of the present invention is to provide a manufactured organic electric battery comprising the novel aromatic amine derivative of the above Chemical Formula 1. Photoluminescent device.
  • a further aspect of the invention is an organic light emitting device comprising a first electrode, a second electrode, and one or more organic compound layers interposed between the two electrodes, wherein at least one organic compound layer comprises at least one A novel aromatic amine compound of the invention.
  • the above novel aromatic amine derivative is a single form or a mixture with other substances including the above organic layer.
  • the organic layer includes at least a hole injection layer, a hole transport layer, a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injecting layer, and It has electronic transmission and any layer in the electron injection skill layer.
  • the hole injection layer, the hole transport layer, and at least one of the hole transporting layer including the hole injection are conventional hole injecting materials, hole transporting materials, and having both hole injecting and cavities.
  • the transmission of skilled substances may also be substances produced by electron-transporting substances.
  • organic layer in this patent refers to the term of all layers disposed between the first electrode and the second electrode of the organic electronic device.
  • the organic layer includes a light-emitting layer, and the organic layer includes one or more of a phosphorescent host, a fluorescent host, phosphorescent doping, and fluorescent doping, including the neo-aromatic amine derivative in the above-mentioned light-emitting layer, i) the fluorescent main body
  • the above-mentioned neoaromatic amine derivative ii) may be the above-mentioned aromatic amine derivative iii)
  • the fluorescent main component and the fluorescent doping may be the above-mentioned neo-aromatic amine derivative.
  • the above-mentioned light-emitting layer may be a red, yellow or cyan light-emitting layer.
  • the above novel aromatic amine derivative is used in a cyan main body or a cyan doping application, and provides an organic light-emitting device having high efficiency, high brightness, high resolution, and long life.
  • the organic layer includes an electron transport layer, and the electron transport layer includes the above novel aromatic amine derivative.
  • the electron transporting layer further comprises a metal-containing compound in addition to the novel aromatic amine derivative.
  • Each of the organic layers includes a light-emitting layer and an electron transport layer, and each of the light-emitting layer and the electron transport layer includes the aromatic amine derivative (the light-emitting layer and the electron transport layer may be the same as or different from the new amine derivative) .
  • the above organic electronic device is prepared by using the novel aromatic amine derivative of the chemical formula 1 together with a conventional material and a method of preparing an organic electronic device.
  • the above device can be used in an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoconductor (OPC), or an organic thin film transistor (OTFT).
  • OLED organic light emitting device
  • OSC organic solar cell
  • e-Paper electronic paper
  • OPC organic photoconductor
  • OTFT organic thin film transistor
  • the organic light-emitting device is formed by vapor deposition, electron beam evaporation, physical vapor deposition or the like on a substrate by vapor deposition of a metal and a conductive oxide and an alloy thereof to form an anode, the hole injection layer, the hole transport layer, and the light emission.
  • the layer, the hole blocking layer and the electron transport layer are prepared by the above method of vapor-depositing the cathode.
  • the organic material layer and the anode material of the cathode material on the substrate are sequentially vapor-deposited to form an organic light-emitting device.
  • the organic layer is a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer, and the organic layer is a solvent-engineered alternative vapor deposition method using various polymer materials. , for example, spin-coating, thin strip
  • Methods such as tape-casting, doctor-blading, screen-printing, inkjet printing, or thermal imaging (Thermal-Imaging) reduce layer manufacturing.
  • the organic device according to the invention may also be illuminated front side, back side or double side depending on the material used.
  • the compound of the present invention is applicable to an organic light-emitting device, such as an organic solar cell, an OLED for illumination, a flexible OLED, an organic photoreceptor, or an organic transistor.
  • an organic light-emitting device such as an organic solar cell, an OLED for illumination, a flexible OLED, an organic photoreceptor, or an organic transistor.
  • Another aspect of the present invention provides a process for producing the above novel aromatic amine derivative, which comprises a substitution reaction, a reduction reaction, a coupling reaction, an amination reaction and the like.
  • reaction formula (1-4) is hydrolyzed to obtain a Q-2 method, and the intermediate of the reaction formula (1-1) and Q-2 are subjected to a reduction reaction to form a new aromatic amine compound.
  • the novel aromatic amine derivative of the present invention is a biscarbazole benzene in which the electron concentration of Ar 1 and Ar 2 is linked by an ether bond, and the related properties are improved, and the molecular weight of the R 1 to R 4 ligand of the biscarbazole is adjusted.
  • the ligand type improves the performance and improves the function.
  • the organic device using an amine derivative in the present invention has high luminance, excellent heat resistance, long life, and high efficiency.
  • Another aspect of the present invention provides a process for producing the above novel aromatic amine derivative, which comprises a substitution reaction, a reduction reaction, a coupling reaction, an amination reaction and the like.
  • reaction formula (1-4) is hydrolyzed to obtain a Q-2 method, and the intermediate of the reaction formula (1-1) and Q-2 are subjected to a reduction reaction to form a new aromatic amine compound.
  • Steps A), B) have no precedence
  • Y 1 is Br, Cl or I
  • L 2 is an integer of 0 to 2 and is not 0;
  • Y 2 and Y 3 are independently selected from -B(OH) 2 or -NH 2 ;
  • X 1 , X 2 are independently selected from Br or I;
  • X 3 , X 4 are independently selected from Cl, Br or I;
  • L 1 is an integer of 0 to 2, when L 1 is 0, Ar 1 is an aryl group having 6 to 30 carbon atoms; when L 1 > 0, Ar 1 is an arylene group, and the Ar 1 does not include benzo Class group
  • Ar 2 is an aralkyl group having 7 to 50 carbon atoms, an aralkyloxy group having 7 to 50 carbon atoms, an aralkyl fluorenyl group having 7 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, and a carbon number.
  • R 1 to R 4 and R′ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 50 carbon atoms, a substitution or Unsubstituted aralkyl fluorenyl group having 7 to 50 carbon atoms, aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic ring having 5 to 50 carbon atoms, and substituted or unsubstituted carbon atom number 6 to 30 Aromatic amines.
  • the benzo group refers to a group in which a benzoheterocyclic compound loses two hydrogen atoms.
  • Will Fisher's coating thickness is The ITO glass substrate was washed twice in distilled water, ultrasonically washed for 30 minutes, washed sequentially with isopropanol, acetone, and methanol for 30 minutes, repeatedly washed twice with distilled water, ultrasonically washed for 10 minutes, dried, and transferred to a plasma cleaning. In the machine, the substrate was washed for 5 minutes and sent to a vapor deposition machine. Evaporation of the hole injection layer 2-TNATA on the prepared ITO transparent electrode Hole transport layer a-NPD or Example E to Example for material evaporation Hole blocking layer and hole transport layer cathode The above process organic evaporation rate is maintained LiF is Al is
  • the present invention is an organic light-emitting device using a novel aromatic amine derivative, and as a result of obtaining good luminous efficiency and longevity, the present invention is useful in the highly practical OLED industry.
  • the organic light-emitting device of the present invention is suitable for use in a flat panel display, a planar light-emitting body, a surface-emitting OLED light-emitting body for illumination, a flexible light-emitting body, a copying machine, a printer, an LCD backlight, or a light source, a display panel, a logo, and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Indole Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un nouveau dérivé d'amine aromatique formé de façon qu'un composé de bis-carbazole se lie à Ar1 et Ar2 par le biais de liaisons éther, et qui est capable d'élever l'intensité d'électrons et d'accroître les propriétés pertinentes, le nouveau dérivé d'amine aromatique selon l'invention présentant en plus les avantages de réguler le poids moléculaire et les variétés concernant les ligands R1 et R4 du bis-carbazole, améliorant ainsi la performance, améliorant les fonctions, et autres. Un dispositif organique utilisant un dérivé d'amine selon l'invention qui présente une luminosité élevée, une excellente résistance à la chaleur, une longue durée de vie et un rendement élevé, pouvant être obtenu par un procédé de synthèse et de purification plus simple, à bas coût, et satisfaisant les exigences d'une production à l'échelle industrielle est en outre décrit.
PCT/CN2015/096421 2015-03-24 2015-12-04 Matériau électroluminescent organique et dispositif préparé à l'aide de celui-ci WO2016150193A1 (fr)

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CN201510128210.3 2015-03-24
CN201510128210.3A CN104829520B (zh) 2015-03-24 2015-03-24 有机电致发光材料及其使用这个有机电致发光材料制备的器件

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Cited By (2)

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WO2020109039A1 (fr) 2018-11-28 2020-06-04 Basf Se Composés pesticides
WO2021219513A1 (fr) 2020-04-28 2021-11-04 Basf Se Composés pesticides

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CN104892434B (zh) * 2015-06-02 2017-03-01 吉林奥来德光电材料股份有限公司 一种化合物和发光器件
CN105523991B (zh) * 2015-12-22 2018-05-01 吉林奥来德光电材料股份有限公司 一种新的咔唑类化合物及其制备方法和应用
CN105384613B (zh) * 2015-12-22 2017-10-27 吉林奥来德光电材料股份有限公司 一种新的有机电致发光材料及其制备方法和应用
CN107619406A (zh) * 2016-07-15 2018-01-23 吉林奥来德光电材料股份有限公司 一种新的咔唑类衍生物及其制备方法和在器件中的应用
CN114195699B (zh) * 2021-12-02 2024-03-19 常州大学 有机小分子手性主体材料及其应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020109039A1 (fr) 2018-11-28 2020-06-04 Basf Se Composés pesticides
WO2021219513A1 (fr) 2020-04-28 2021-11-04 Basf Se Composés pesticides

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